TRAILER BRIDGE INC
S-1/A, 1997-06-30
TRUCKING (NO LOCAL)
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<PAGE>   1
 
   
     AS FILED WITH THE SECURITIES AND EXCHANGE COMMISSION ON JUNE 30, 1997
    
 
   
                                                      REGISTRATION NO. 333-28221
    
================================================================================
 
                       SECURITIES AND EXCHANGE COMMISSION
                             WASHINGTON, D.C. 20549
                               ------------------
   
                                AMENDMENT NO. 1
    
   
                                       TO
    
 
                                    FORM S-1
                             REGISTRATION STATEMENT
                                     UNDER
                           THE SECURITIES ACT OF 1933
                               ------------------
 
                              TRAILER BRIDGE, INC.
             (Exact name of Registrant as specified in its charter)
                             ---------------------
 
<TABLE>
<S>                             <C>                             <C>
           DELAWARE                          4213                         13-3617986
(State or other jurisdiction of  (Primary Standard Industrial          (I.R.S. Employer
incorporation or organization)    Classification Code Number)         Identification No.)
</TABLE>
 
                    9550 REGENCY SQUARE BOULEVARD, SUITE 500
                          JACKSONVILLE, FLORIDA 32225
                                 (904) 724-4400
 
         (Address, including zip code, and telephone number, including
            area code, of Registrant's principal executive offices)
                               ------------------
                                 RALPH W. HEIM
                     PRESIDENT AND CHIEF OPERATING OFFICER
                              TRAILER BRIDGE, INC.
                    9550 REGENCY SQUARE BOULEVARD, SUITE 500
                          JACKSONVILLE, FLORIDA 32225
                                 (904) 724-4400
 
   
      (Name, address, including zip code, and telephone number, including
    
                        area code, of agent for service)
                               ------------------
                                   Copies to:
 
   
<TABLE>
<C>                             <C>                             <C>
WILLIAM G. GOTIMER, JR., ESQ.        LINDA Y. KELSO, ESQ.         BRUCE E. MACDONOUGH, ESQ.
     TRAILER BRIDGE, INC.              FOLEY & LARDNER            GREENBERG TRAURIG HOFFMAN
  500 PARK AVENUE, SUITE 540           200 LAURA STREET          LIPOFF ROSEN & QUENTEL, P.A.
   NEW YORK, NEW YORK 10022      JACKSONVILLE, FLORIDA 32202         1221 BRICKELL AVENUE
        (212) 935-9518                  (904)359-2000                MIAMI, FLORIDA 33131
                                                                        (305) 579-0500
</TABLE>
    
 
                               ------------------
     APPROXIMATE DATE OF COMMENCEMENT OF PROPOSED SALE TO THE PUBLIC: As soon as
practicable after the effective date of this Registration Statement.
                        CALCULATION OF REGISTRATION FEE
 
   
<TABLE>
<CAPTION>
================================================================================================================
                                                             PROPOSED          PROPOSED
                                            AMOUNT            MAXIMUM           MAXIMUM           AMOUNT OF
TITLE OF EACH CLASS OF SECURITIES TO        TO BE         OFFERING PRICE       AGGREGATE        REGISTRATION
           BE REGISTERED                REGISTERED(1)        PER UNIT       OFFERING PRICE         FEE(2)
- ----------------------------------------------------------------------------------------------------------------
<S>                                   <C>                <C>               <C>               <C>
Common Stock $.01 par value.........   3,105,000 shares       $13.00          $40,365,000       $12,231.82(3)
================================================================================================================
</TABLE>
    
 
   
(1) Includes 405,000 shares of Common Stock issuable upon exercise of an
    over-allotment option granted to the Underwriters.
    
(2) Estimated solely for the purpose of calculating the registration fee
    pursuant to Rule 457 under the Securities Act of 1933.
   
(3) The Registrant has previously paid a fee of $9,393.94.
    
                               ------------------
     THE REGISTRANT HEREBY AMENDS THIS REGISTRATION STATEMENT ON SUCH DATE OR
DATES AS MAY BE NECESSARY TO DELAY ITS EFFECTIVE DATE UNTIL THE REGISTRANT SHALL
FILE A FURTHER AMENDMENT WHICH SPECIFICALLY STATES THAT THIS REGISTRATION
STATEMENT SHALL THEREAFTER BECOME EFFECTIVE IN ACCORDANCE WITH SECTION 8(A) OF
THE SECURITIES ACT OF 1933 OR UNTIL THE REGISTRATION STATEMENT SHALL BECOME
EFFECTIVE ON SUCH DATE AS THE COMMISSION, ACTING PURSUANT TO SAID SECTION 8(A),
MAY DETERMINE.
================================================================================
<PAGE>   2
 
     INFORMATION CONTAINED HEREIN IS SUBJECT TO COMPLETION OR AMENDMENT. A
     REGISTRATION STATEMENT RELATING TO THESE SECURITIES HAS BEEN FILED WITH THE
     SECURITIES AND EXCHANGE COMMISSION. THESE SECURITIES MAY NOT BE SOLD NOR
     MAY OFFERS TO BUY BE ACCEPTED PRIOR TO THE TIME THE REGISTRATION STATEMENT
     BECOMES EFFECTIVE. THIS PROSPECTUS SHALL NOT CONSTITUTE AN OFFER TO SELL OR
     THE SOLICITATION OF AN OFFER TO BUY NOR SHALL THERE BE ANY SALE OF THESE
     SECURITIES IN ANY STATE IN WHICH SUCH OFFER, SOLICITATION OR SALE WOULD BE
     UNLAWFUL PRIOR TO REGISTRATION OR QUALIFICATION UNDER THE SECURITIES LAWS
     OF ANY SUCH STATE.
 
                                                           SUBJECT TO COMPLETION
   
                                                                   JUNE 30, 1997
    
 
   
                                2,700,000 Shares
    
 
                            [Trailer Bridge Logo]
 
                              TRAILER BRIDGE, INC.
                                  Common Stock
                               ------------------
 
   
     All of the shares of Common Stock offered hereby are being sold by Trailer
Bridge, Inc. ("Trailer Bridge" or the "Company"). Prior to this offering, there
has been no public market for the Common Stock of the Company. It is currently
estimated that the initial public offering price will be between $11.00 and
$13.00 per share. See "Underwriting" for a discussion of the factors to be
considered in determining the initial public offering price. The Company has
made application for the Common Stock to be quoted on the Nasdaq National Market
under the symbol "TRBR."
    
 
   
     Existing stockholders will beneficially own approximately 71% of the
outstanding Common Stock after the offering. See "Principal Stockholders."
Approximately $6.2 million of the net proceeds of the offering will be used to
repay indebtedness of the Company to an affiliate and $6.0 million will be used
to pay an S Corporation dividend to existing stockholders. See "Use of
Proceeds." The Common Stock is subject to certain restrictions on ownership by
non-U.S. citizens designed to maintain the Company's eligibility to own and
operate vessels in the U.S. domestic trade. Non-U.S. citizens will be required
to redeem or sell their Common Stock if ownership of the Common Stock by
non-U.S. citizens exceeds these restrictions. See "Description of Capital
Stock -- Foreign Ownership Restrictions and Possible Divestiture of Stock."
    
 
                               ------------------
 
   
     THE COMMON STOCK OFFERED HEREBY INVOLVES A HIGH DEGREE OF RISK. SEE "RISK
FACTORS" BEGINNING ON PAGE 8.
    
                               ------------------
 
  THESE SECURITIES HAVE NOT BEEN APPROVED OR DISAPPROVED BY THE SECURITIES AND
 EXCHANGE COMMISSION OR ANY STATE SECURITIES COMMISSION NOR HAS THE SECURITIES
   AND EXCHANGE COMMISSION OR ANY STATE SECURITIES COMMISSION PASSED UPON THE
ACCURACY OR ADEQUACY OF THIS PROSPECTUS. ANY REPRESENTATION TO THE CONTRARY IS A
                               CRIMINAL OFFENSE.
 
   
<TABLE>
<CAPTION>
=============================================================================================================
                                                                  UNDERWRITING
                                           PRICE TO              DISCOUNTS AND             PROCEEDS TO
                                            PUBLIC                COMMISSIONS               COMPANY(1)
- -------------------------------------------------------------------------------------------------------------
<S>                                <C>                      <C>                      <C>
Per Share.........................            $                        $                        $
- -------------------------------------------------------------------------------------------------------------
Total.............................            $                        $                        $
=============================================================================================================
</TABLE>
    
 
   
(1) Before deducting expenses of the offering estimated at $332,000.
    
 
   
(2) The Company has granted the Underwriters a 30-day option to purchase up to
    an additional 405,000 shares of Common Stock solely to cover over
    allotments, if any. To the extent that the option is exercised, the
    Underwriters will offer the additional shares to the public at the Price to
    Public shown above. If the option is exercised in full, the total Price to
    Public, Underwriting Discounts and Commissions and Proceeds to Company will
    be $          , $          and $          , respectively. See
    "Underwriting."
    
 
                               -----------------------
 
     The shares of Common Stock are offered by the several Underwriters, subject
to prior sale, when, as and if delivered to and accepted by them, and subject to
the right of the Underwriters to reject any order in whole or in part. It is
expected that delivery of the shares of Common Stock will be made at the offices
of Alex. Brown & Sons Incorporated, Baltimore, Maryland, on or about
  , 1997.
 
                               ALEX. BROWN & SONS
                                  INCORPORATED
 
               THE DATE OF THIS PROSPECTUS IS             , 1997.
<PAGE>   3
Omitted Graphic and Image Material

        The following is a narrative description of graphic and image material
contained in the printed version of the Prospectus which has been omitted from
the version filed electronically.


Inside front cover:

        Three photographs (counterclockwise from the top) depicting (i)
        a Trailer Bridge tractor and trailer leaving a customer's premises,
        (ii) a trailer being pulled onto one of the Company's tripledeck
        barges, and (iii) the loaded barge being towed out to the open sea.









 
   
     CERTAIN PERSONS PARTICIPATING IN THIS OFFERING MAY ENGAGE IN TRANSACTIONS
THAT STABILIZE, MAINTAIN OR OTHERWISE AFFECT THE PRICE OF THE COMMON STOCK,
INCLUDING BY ENTERING STABILIZING BIDS, EFFECTING SYNDICATE COVERING
TRANSACTIONS OR IMPOSING PENALTY BIDS. FOR A DESCRIPTION OF THESE ACTIVITIES,
SEE "UNDERWRITING."
    
 
     The Company intends to furnish its stockholders with annual reports
containing audited financial statements and an opinion thereon expressed by
independent certified public accountants and with quarterly reports for the
first three quarters of each year containing unaudited financial information.
 
                                        2
<PAGE>   4
 
                               PROSPECTUS SUMMARY
 
   
     The following summary is qualified in its entirety by the more detailed
information and the financial statements and notes thereto appearing elsewhere
in this Prospectus. Except as otherwise specified, all information in this
Prospectus assumes (i) a 15,700-for-one split of the shares of Common Stock, and
(ii) no exercise of the Underwriters' over-allotment option. See "Underwriting."
    
 
                                  THE COMPANY
 
   
     Trailer Bridge, headquartered in Jacksonville, Florida, is an integrated
trucking and marine freight carrier that provides truckload freight
transportation primarily between the continental U.S. and Puerto Rico. Founded
in 1991 by transportation pioneer Malcom P. McLean, the Company combines an
efficient and dedicated motor carrier with a low cost barge and tug marine
transportation system. Trailer Bridge is the only company serving markets
governed by the Jones Act which exclusively operates marine vessels fully
configured to carry 48' and 53' long, 102" wide, "high-cube" trailers. This
configuration enables the Company to achieve equipment utilization rates and
other operating efficiencies not readily available to traditional ocean carriers
that primarily use smaller capacity equipment, such as 40' containers. The
Company believes that as a result of these and other efficiencies, its total
unit costs per mile are the lowest of any carrier operating between the
continental U.S. and Puerto Rico.
    
 
   
     Trailer Bridge intends to achieve significant growth by providing the
lowest cost freight transportation service to markets well suited to its
high-cube integrated truckload and marine freight system. Based on volume and
pricing data, the Company believes that there are a number of markets in which
the Company's unique transportation system can provide superior full-load
service at a significant cost advantage over existing modes of truckload and
rail intermodal transportation.
    
 
   
     Trailer Bridge's differentiated service quickly gained the acceptance of
U.S. to Puerto Rico shippers, leading to rapid growth and high equipment
utilization. In 1993, the Company's first full year of operation, Trailer Bridge
achieved a 93% outbound (continental U.S. to Puerto Rico) vessel utilization
rate and captured 5% of the continental U.S. to Puerto Rico marine freight
market. In response to the rapid market share gains experienced by Trailer
Bridge, in 1996 the Company increased its vessel capacity by 56% by inserting
midsections ("mid-bodies") into its two existing barges, increasing the capacity
of each barge from 266 to 416 48' equivalent truckload units. These
roll-on/roll-off barges are chartered from an affiliate.
    
 
   
     Trailer Bridge will increase its vessel capacity by an additional 56% in
late 1997 and early 1998 when it takes delivery of two 408' long container
carrying barges designed specifically for the Company's integrated truckload
marine transportation system and bearing the Company's Triplestack Box
Carrier(TM) trade name. The Triplestack Box Carriers(TM) will be versatile,
low-draft vessels that have a capacity of 213 53' containers, stacked three-high
on a single deck. Construction of these two vessels began in March 1997. Upon
completion, the vessels will be deployed in the Company's existing Puerto Rico
freight operation. Trailer Bridge also intends to contract for the construction
of three additional Triplestack Box Carriers(TM) which it intends to deploy in
coastwise service between New York and Florida. The Company plans to investigate
other marine markets which are well suited for its unique, cost-efficient
transportation service, such as from the continental U.S. to Hawaii or Alaska.
    
 
     Management believes that the Company's principal competitive strengths are:
 
   
          Significant Operating Cost Advantage.  Trailer Bridge believes that it
     is the lowest cost provider of freight transportation between the
     continental U.S. and Puerto Rico. Lower overall operating costs are
     achieved through significantly higher equipment utilization and lower
     marine linehaul costs than those of traditional ocean carriers. The
     Company's inland trucking operation achieves higher equipment utilization
     and lower unit trucking costs by using 48' and
    
                                        3
<PAGE>   5
 
     53' high-cube trailers. These trailers provide customers with over 50% more
     interior capacity than 40' marine containers but with similar inland
     trucking costs. The Company's marine system uses towed ocean-going barges
     instead of self-propelled container ships to deliver equivalent units of
     capacity at significantly lower capital and operating costs.
 
   
          Domestic Truckload Operations.  The Company believes that it is the
     only carrier using its own fleet of tractors and high-cube dry van trailers
     to provide transportation services between interior points within the
     continental U.S. and Puerto Rico. By using high-cube equipment, the
     mainstay of the domestic truckload industry and a centralized dispatch
     system, the Company can more effectively compete for and obtain domestic
     non-Puerto Rico truckload freight while repositioning equipment for Puerto
     Rico shipments. As a result, the Company believes that it operates with
     lower empty miles and higher equipment utilization than its competitors in
     the Puerto Rico trade.
    
 
   
          Centralized Operation in Strategic Location.  Trailer Bridge operates
     a centralized truckload operation from its headquarters in Jacksonville.
     Because approximately 70% of the Company's truckload freight is dispatched
     through Jacksonville on a regular schedule to meet weekly barge sailings to
     Puerto Rico, the Company is able to achieve purchasing, maintenance and
     other operating efficiencies and higher driver retention. Additionally, the
     Company's centralized Jacksonville headquarters is strategically located
     near key southern rail and highway endpoints which connect U.S. cities to
     Puerto Rico and other Caribbean points.
    
 
   
          Emphasis on U.S. Domestic Ocean Trade.  The Company concentrates its
     marine operations in markets governed by the Jones Act. The Jones Act
     prevents foreign-built or foreign-crewed vessels from competing in ocean
     trade between ports in the U.S., including the non-contiguous areas of
     Puerto Rico, Alaska, Hawaii and Guam.
    
 
   
          Experienced Management Team.  The Company's officers and directors
     have extensive experience in the transportation industry, including an
     average of over 15 years in the marine and trucking industries. All but one
     member of the Company's management team have been with the Company since
     its inception. The scope of management experience at Trailer Bridge is well
     balanced between both trucking and marine transportation.
    
 
   
     Trailer Bridge's strategy for continuing its profitable growth includes (i)
increasing capacity in its Puerto Rico service by 56% with the addition of two
new Triplestack Box Carriers(TM), (ii) initiating a new coastwise marine
transportation service that will offer twice-weekly sailings from New York to
Florida utilizing three additional Triplestack Box Carriers(TM) to be built in
1998, and (iii) initiating marine service to other Jones Act protected markets
such as Hawaii and Alaska.
    
 
   
     Trailer Bridge was incorporated under the laws of Delaware in April 1991.
The Company's headquarters is located at 9550 Regency Square Blvd, Jacksonville,
Florida 32225, and its telephone number is (800) 554-1589.
    
                                        4
<PAGE>   6
 
                                  THE OFFERING
 
   
Common Stock offered hereby.................    2,700,000 shares
    
 
   
Common Stock to be outstanding after the
offering....................................    9,372,500 shares (1)
    
 
   
Use of Proceeds.............................    To purchase revenue equipment
                                                ($13.2 million), reduce
                                                indebtedness to an affiliate
                                                ($6.2 million), fund an S
                                                Corporation dividend to existing
                                                stockholders ($6.0 million),
                                                partially fund the acquisition
                                                of new vessels ($2.2 million)
                                                and increase working capital
                                                ($2.2 million). Dollar amounts
                                                are approximations. See "Use of
                                                Proceeds."
    
 
Proposed Nasdaq National Market Symbol......    TRBR
- ---------------
 
   
(1) Excludes 785,000 shares of Common Stock reserved for issuance to employees
    under the Company's Incentive Stock Plan (of which options to purchase
    471,000 shares at the initial public offering price have been granted). See
    "Management -- Incentive Stock Plan."
    
                                        5
<PAGE>   7
 
                      SUMMARY FINANCIAL AND OPERATING DATA
   
          (In thousands, except per share amounts and operating data)
    
 
   
<TABLE>
<CAPTION>
                                                                                                 THREE MONTHS
                                                                                                     ENDED
                                                      YEAR ENDED DECEMBER 31,                      MARCH 31,
                                          ------------------------------------------------     -----------------
                                            1992      1993      1994      1995     1996(1)     1996(1)    1997
                                          --------   -------   -------   -------   -------     -------   -------
<S>                                       <C>        <C>       <C>       <C>      <C>          <C>       <C>
STATEMENT OF OPERATIONS DATA:
  Operating revenues....................  $ 38,778   $67,613   $72,192   $62,531  $63,148     $14,568   $16,446
  Operating income (loss)...............    (9,309)    5,094     6,175     8,778    4,425         966      1,748
  Nonoperating expense (net)............      (864)     (944)   (1,805)   (1,314)  (1,015)       (256)      (264)
  Income (loss) before provision and pro
    forma provision (benefit) for income
    taxes...............................   (10,173)    4,150     4,370     7,464    3,410         710      1,484
  Pro forma net income (loss)(2)........    (6,313)    2,526     2,343     4,360    2,073         443        909
  Pro forma net income per common
    share(3)............................                                          $   .29                $   .13
  Pro forma weighted average shares
    outstanding(3)......................                                            7,173                  7,173
  Supplementary pro forma net income per
    common share(4).....................                                          $   .30                $   .12
OPERATING DATA:
  Operating ratio(5)....................     124.0%     92.5%     91.4%     86.0%    93.0%       93.4%      89.4%
  Vessel utilization outbound...........      60.1%     93.5%     90.9%     96.0%    88.4%(6)    96.3%      78.1%(6)
  Vessel utilization inbound............      12.1%     36.6%     52.8%     51.6%    42.0%(6)    59.8%      33.6%(6)
  Overall vessel capacity utilization...      36.1%     65.0%     71.8%     73.8%    65.3%(6)    78.1%      55.8%(6)
  Tractor loaded mile percentage........      77.3%     87.1%     86.2%     81.0%    81.5%       83.0%      80.5%
  Weighted average tractors.............       178       199       256       187      163         174        154
  Weighted average trailers.............       923     1,629     1,605     1,458    1,762       1,400      1,983
</TABLE>
    
 
   
<TABLE>
<CAPTION>
                                                                  MARCH 31, 1997         PRO FORMA
                                                              -----------------------       AS
                                                               ACTUAL    PRO FORMA(7)   ADJUSTED(8)
                                                              --------   ------------   -----------
<S>                                                           <C>        <C>            <C>
BALANCE SHEET DATA:
  Working capital (deficit).................................  $ (2,823)    $(8,823)(9)    $ 5,577
  Net property and equipment................................    14,349      14,349         27,549
  Total assets..............................................    26,440      26,440         44,362
  Long-term debt, capital lease obligations and due to
    affiliate(10)...........................................    15,242      15,242          9,364
  Stockholders' equity......................................     6,314         314         29,464
</TABLE>
    
 
- ---------------
 
   
 (1) During 1996, each of the Company's barge vessels was increased in size
     through a mid-body expansion program that resulted in a 56% increase in
     vessel capacity and was accomplished over a six-month period. From
     mid-February through mid-July 1996, only one of the Company's vessels was
     in service at a time. To maintain weekly service frequency, a smaller
     substitute vessel was utilized, resulting in both reduced revenue and
     additional costs. For these reasons, management believes that overall 1996
     results are not indicative of the results that would have been expected had
     both of the Company's vessels remained in service throughout the year.
    
   
 (2) Since January 1, 1992, the Company has operated as an S Corporation under
     the Internal Revenue Code and the laws of the states that recognize S
     Corporation status. As a result, the Company's taxable earnings were taxed
     directly to the Company's then-existing stockholders. Pro forma net income
     assumes that the Company was subject to federal and state income taxes and
     was taxed as a C Corporation at the effective tax rates that would have
     applied for all periods. See Note 2 to the Financial Statements. With the
     closing of the offering, the Company will become subject to federal and
     state income taxes. The pro forma statement of operations data do not give
     effect to a non-cash charge (that would have been approximately $650,000 at
     March 31, 1997) in recognition of deferred income taxes that will result
     from the termination of the Company's S Corporation status upon
     effectiveness of the offering.
    
                                        6
<PAGE>   8
 
   
 (3) Pro forma net income per share reflects a 15,700-for-1 stock split that
     will become effective in connection with the offering and the issuance of
     500,000 shares of Common Stock to fund the payment of a $6.0 million S
     Corporation dividend to existing stockholders with a portion of the net
     proceeds of the offering.
    
   
 (4) The Company expects to use a portion of the net proceeds from the offering
     to repay amounts due to affiliate. Supplementary pro forma net income per
     share reflects the interest savings and the issuance of approximately
     652,000 shares of Common Stock to fund the repayment, assuming the issuance
     and repayment had occurred on January 1, 1996.
    
   
 (5) Operating expenses as a percentage of revenue.
    
   
 (6) From mid-February through mid-July 1996, only one of the Company's two
     vessels was in service at a time due to the Company's mid-body expansion
     program, and the Company operated during this period with a second, smaller
     substitute vessel. Vessel capacity outbound to Puerto Rico and inbound to
     the U.S. increased from 266 48' trailer equivalents at February 1, 1996 to
     416 48' trailer equivalents at July 31, 1996.
    
   
 (7) Adjusted to reflect the $6.0 million S Corporation dividend to be paid to
     existing stockholders with a portion of the net proceeds of the offering.
    
   
 (8) Adjusted to reflect (i) the sale of 2,700,000 shares of Common Stock
     offered by the Company at an assumed price of $12.00 per share and the
     application of the estimated net proceeds therefrom as described under "Use
     of Proceeds," and (ii) a non-cash charge (that would have been
     approximately $650,000 at March 31, 1997) that will result from the
     termination of the Company's S Corporation status. See "S Corporation
     Status."
    
   
 (9) Reflects short-term obligation to fund dividend payable to existing
     stockholders.
    
   
(10) Includes current maturities.
    
                                        7
<PAGE>   9
 
                                  RISK FACTORS
 
     In addition to the other information in this Prospectus, the following risk
factors should be considered carefully in evaluating an investment in the
Company's Common Stock.
 
OPERATIONS DEPENDENT ON LIMITED FLEET AND SPECIAL LOADING STRUCTURES
 
     The Company's current operations are dependent upon two vessels and triple
deck loading ramps at the Company's port facilities in Jacksonville, Florida and
San Juan, Puerto Rico, the loss of any of which could have a material adverse
effect on the Company. The operation of any marine vessel involves the risk of
catastrophic events due to various perils of sea. In addition, port facilities
in Jacksonville and San Juan are vulnerable to the risk of hurricanes. In the
event of either a total loss of or major damage to any vessel or ramp, there can
be no assurance that the Company could locate a suitable replacement, or if
available, that such replacement could be obtained on suitable terms. The
Company also would be adversely affected if unexpected maintenance or repairs
were required for any vessel or ramp, all of which have been specially
configured for the Company. The Company does not maintain business interruption
insurance. Accordingly, there can be no assurance that the loss of, damage to or
significant required repair to any of the Company's vessels or port facilities
in the future would not have a material adverse effect on the Company.
 
CURRENT RELIANCE ON SINGLE MARKET
 
   
     Most of the Company's present revenue is attributable to freight moving
either to or from Puerto Rico. Freight moving to or from Puerto Rico accounted
for 89.2% of the Company's revenue in 1996 and 93.5% during the three months
ended March 31, 1997. The Company's current results are therefore affected by
economic conditions and business cycles in Puerto Rico that may or may not be
similar to those in the U.S. The Company's present reliance on the Puerto Rico
market makes it susceptible to changes that it would not otherwise be exposed to
if it operated in a more geographically diverse market, including a downturn in
the local economy, local economic and competitive factors, changes in government
regulations and political changes. The U.S. Congress has passed legislation that
establishes a phase-out of Section 936 of the Internal Revenue Code, which
allows for favorable U.S. tax treatment of profits resulting from manufacturing
operations in Puerto Rico. The phase-out began in January 1996 and continues
until January 2006. This favorable tax provision has contributed to economic
growth in Puerto Rico in the past by enticing U.S. corporations to establish
manufacturing operations in Puerto Rico. Any change in Puerto Rico's political
status with the U.S., or the ongoing debate on such status, could affect the
economy of Puerto Rico. The ultimate effect of the phase-out of Section 936 or
of possible changes in Puerto Rico's governmental and political status is
uncertain and, accordingly, there can be no assurance that such issues will not
adversely affect the Company.
    
 
NEW VENTURE RISKS
 
     A key element of the Company's strategy for future growth is to expand into
new markets, including the domestic coastwise traffic lanes such as New York to
Florida, while continuing to build the Company's presence in the Puerto Rico
market. In addition, the Company's expansion in both the Puerto Rico and
coastwise traffic lanes will be accomplished with its new Triplestack Box
Carrier(TM) vessels which will require the Company's acquisition of containers,
chassis units and loading equipment that may not be compatible with the
Company's existing vessels and revenue equipment. The planned use of Triplestack
Box Carriers(TM) and expansion into coastal traffic lanes are subject to risks
of establishing a new business, including lack of experience, unforeseen design,
operating and maintenance problems and lack of market acceptance. In the case of
the coastwise traffic lanes, there is presently no comparable marine service and
the Company will be competing with the rail intermodal and truckload industries.
Many competitors in these industries have substantially greater financial
resources, operate more equipment, or carry a larger volume of freight than the
Company. Moreover, the expansion in Puerto Rico with the Triplestack Box
Carriers(TM) and
 
                                        8
<PAGE>   10
 
   
the entry into new coastal traffic lanes will require new marketing strategies,
additional personnel and a continuing evaluation of management structure. No
assurance can be given that Trailer Bridge will be able to attract a sufficient
number of customers at freight rates that result in profitable operations in
Puerto Rico, the Company's anticipated new traffic lanes and the markets it
expects to expand into in the future. See "Business -- Growth Strategy."
    
 
SHIP CONSTRUCTION RISKS
 
   
     The Company has entered into a fixed-price contract for the Company's two
Triplestack Box Carriers(TM), and construction has commenced with the first
vessel scheduled for delivery in November 1997 and the second vessel scheduled
for delivery two months later. No assurance can be given that there will be no
changes in the contract specifications, either as required by various regulatory
bodies or as requested by the Company, which result in an increase in
construction cost and/or a delay in the delivery of the vessels. Construction of
the Triplestack Box Carriers(TM) also involves the risks associated with any
large construction project, such as weather interference, labor shortages, work
stoppages and unforeseen engineering problems, any of which could have the
effect of increasing project costs and/or delaying delivery. During the
construction of a vessel, as a matter of state law, laborers and others who
perform services in connection with such construction may have liens against the
vessel under construction.
    
 
RAPID GROWTH OF BUSINESS
 
   
     The Company expects to increase its capacity by approximately 56% between
October 31, 1997 and January 31, 1998. This new vessel capacity will result in a
need for additional revenue equipment (tractors and trailers) and drivers. There
can be no assurance that the Company will be able to attract and retain enough
qualified drivers to operate planned additions to the equipment fleet. Further,
expected growth, if achieved, may place a significant strain on the Company's
management, working capital, and accounting and other operating systems. There
is no assurance that such systems will be adequate to handle such growth or that
operating margins will not be adversely affected by future changes in and
expansion of the Company's business. Finally, the Company may be required to
curtail its plans for growth due to changes in economic conditions.
    
 
POTENTIAL LOSS OF JONES ACT PROTECTION
 
   
     The Company's marine operations are conducted in the U.S. domestic trade,
which, by virtue of a set of federal laws known as the Jones Act, require that
only U.S. built, owned and crewed vessels move freight between ports in the
U.S., including the non-contiguous areas of Puerto Rico, Alaska, Hawaii and
Guam. There have been repeated attempts to repeal these laws, and efforts to
effect such repeal are expected to continue in the future. The Company is
already subject to vigorous competition and potential additional competition in
its marine operations, including competition by companies with financial
resources greater than those of the Company that could be committed to the
construction of new vessels in excess of market requirements. Repeal of or
significant changes to the Jones Act could result in additional competition from
vessels built in lower-cost foreign shipyards and manned by foreign nationals
accepting lower wages than U.S. citizens. There is no assurance that such repeal
or changes would not have a material adverse effect on the Company in the
domestic trades it now serves or expects to serve in the future.
    
 
ECONOMIC FACTORS
 
   
     The Company has no control over economic factors such as fuel prices, fuel
tax, interest rate fluctuations, recessions or customers' business cycles.
Significant increases in fuel or other operating costs and interest rates, to
the extent not offset by increases in freight rates, would adversely affect the
Company's operating results. Economic recessions, temporary inventory imbalances
or downturns in customers' business cycles also could have a material adverse
effect upon the operating results of the Company. If the resale value of the
Company's revenue equipment were to decline, the
    
 
                                        9
<PAGE>   11
 
Company could receive less upon the disposition of equipment or find it
necessary to retain its equipment longer, with a resulting increase in operating
expenses. The marine and trucking industries are cyclical with corresponding
changes in revenue and profits. Changes in the level of economic growth as well
as changes in the supply and demand of vessel and trucking capacity can impact
both rates and resale values. The amount and timing of new vessel deliveries to
competing carriers in the Puerto Rico market and rate reductions from increased
capacity, excess capacity or slow market growth could result in rate instability
that could have a material adverse effect upon the Company. See "Management's
Discussion and Analysis of Financial Condition and Results of Operations."
 
RECRUITMENT AND RETENTION OF QUALIFIED DRIVERS
 
     Competition for drivers is intense in the trucking industry, and the
Company occasionally experiences difficulty attracting and retaining enough
qualified drivers. There is, and historically has been, an industry-wide
shortage of qualified drivers, and this shortage could affect the quality and
reliability of the Company's service, force the Company to significantly
increase the compensation it pays to driver employees, curtail the Company's
growth or otherwise affect the Company's profitability. Difficulty in attracting
and retaining qualified drivers would have a material adverse effect upon the
Company's operations and ability to grow. See "Business -- Driver Recruiting and
Retention."
 
ACQUISITION OF REVENUE EQUIPMENT
 
     The Company's strategy for continued growth is dependent on the acquisition
and deployment of additional revenue equipment. The Company currently has orders
for the purchase of 100 tractors through February 1998 as part of its normal
tractor replacement program. The Company also has contracted for the
construction of 53' containers and chassis units whose delivery is expected to
coincide with the vessel construction schedule for its new Triplestack Box
Carriers(TM). Delays in the availability of equipment could occur due to work
stoppages at the manufacturer, equipment or supply shortages or other factors
beyond the Company's control. Any delay or interruption in the availability of
equipment in the future could have a material adverse effect on the Company.
 
COMPETITION
 
   
     The trucking industry is highly competitive and fragmented and the Puerto
Rico freight market is also highly competitive. The Company currently competes
with other truckload carriers that provide domestic dry van service, private
fleets operated by existing and potential customers, and marine carriers that
provide ocean service between the continental U.S. and Puerto Rico. The
Company's planned service in the coastwise traffic lanes will compete with rail
intermodal service and trucking companies. Competition for the freight
transported by the Company is based primarily on freight rates, and, to a lesser
degree, on service and efficiency. Most of the Company's current and future
competitors have substantially greater financial resources, operate more
equipment, or carry a larger volume of freight than the Company. See
"Business -- Competition."
    
 
DEPENDENCE ON KEY PERSONNEL
 
   
     The Company's success depends upon key members of management, particularly
John D. McCown. The loss of Mr. McCown could have a material adverse effect on
the Company. The Company does not maintain key man life insurance policies on
any of its officers or management.
    
 
   
     Because Mr. McCown also serves as President and Chief Executive Officer of
the Company's affiliate that owns the two barges operated by the Company, he
will not devote 100% of his working time to Trailer Bridge. It is anticipated
that he will devote less than 5% of his working time to his duties with the
affiliate. See "Management."
    
 
                                       10
<PAGE>   12
 
SEASONALITY
 
     The Company's operations are affected by the seasonality of the Puerto Rico
freight market where shipments are generally reduced during the first calendar
quarter and increased during the fourth calendar quarter of each year in
anticipation of Christmas. This seasonality is expected to have a greater impact
on the Company when it increases its capacity with the addition of two new
Triplestack Box Carriers(TM). In addition, the Company's operating expenses have
historically been higher in the winter months due to decreased fuel efficiency
and increased maintenance costs in colder weather. The Company's operating
revenue and net income may vary as a result of these factors, and accordingly,
results of operations are subject to fluctuation, and results in any period
should not be considered indicative of the results to be expected for any future
period. Fluctuations in operating results may also result in fluctuations in the
price of the Common Stock. See "Management's Discussion and Analysis of
Financial Condition and Results of Operations -- Seasonality."
 
FUEL PRICE FLUCTUATIONS
 
     Fuel is one of the Company's largest operating expenses and was 9.5% of
total revenue for the three months ended March 31, 1997. The cost and
availability of fuel is subject to many economic and political factors. Any
increase in fuel taxes or fuel prices, to the extent not offset by freight rate
increases, or any interruption in the supply of fuel, could have a material
adverse effect on the Company's operating results. The Company has no agreement
in place that assures either price or availability and a dramatic increase in
the price of fuel or a shortage of fuel could have a material adverse impact on
the Company. See "Business -- Fuel Availability and Cost."
 
ENVIRONMENTAL MATTERS
 
   
     The Company's operations are subject to various environmental laws and
regulations dealing with the transportation, storage, presence, use, disposal
and handling of hazardous materials and hazardous wastes, discharge of storm
water and vessel fuel delivery. The Company does not maintain either aboveground
or underground fuel storage tanks on its properties. Contractors under the
direction of the tug owner handle the delivery of fuel to ocean-going tugs. The
Company is not aware of any fuel spills on land or at sea or hazardous substance
contamination on its properties and believes that its operations are in material
compliance with existing environmental laws and regulations. However, if any
such substances were found on the Company's properties or if the Company were
found to be in violation of applicable laws and regulations, the Company could
be responsible for clean-up costs, property damage, and fines or other
penalties, any one of which could have a material adverse effect on the Company.
    
 
CLAIMS EXPOSURE AND INSURANCE COSTS
 
   
     Trucking and marine transportation companies, including the Company, face
multiple claims for personal injury and property damage relating to accidents,
cargo damage and workers' compensation. The Company currently maintains a broad
range of liability and property insurance covering its business. To the extent
that the Company experiences a material increase in the frequency or severity of
accidents or workers' compensation claims, or unfavorable developments on
existing claims, the Company's operating results and financial condition could
be materially adversely affected. Significant increases in the Company's claims
and insurance cost, to the extent not offset by rate increases, would reduce the
Company's profitability. See "Business -- Safety and Insurance."
    
 
GOVERNMENT REGULATION
 
   
     The Company is subject to regulation by various federal and state agencies,
including the Surface Transportation Board, the successor agency to the
Interstate Commerce Commission, the United States Department of Transportation,
the U.S. Coast Guard and various similar state agencies.
    
 
                                       11
<PAGE>   13
 
These regulatory authorities have broad powers, generally governing activities
such as authority to engage in motor carrier operations, operational safety,
accounting systems, tariff filings of freight rates, certain mergers,
consolidations and acquisitions, and financial reporting. The Company's marine
operations are conducted in the U.S. domestic trade, which, by virtue of a set
of federal laws known as the Jones Act, require that only U.S. built, owned and
crewed vessels move freight between ports in the U.S., including the
noncontiguous areas of Puerto Rico, Alaska, Hawaii and Guam. The Company is also
subject to regulations promulgated by the Environmental Protection Agency and
similar state agencies. Although management believes that its operations are in
material compliance with current laws and regulations, there can be no assurance
that current regulatory requirements will not change or that currently
unforeseen environmental incidents will not occur or that contamination or past
noncompliance with environmental laws will not be discovered on properties on
which the Company has operated. See "Business -- Regulation."
 
RELIANCE ON SIGNIFICANT CUSTOMERS
 
   
     For the year ended December 31, 1996, the Company's 25 largest customers
represented 35.2% of revenue, its ten largest customers represented 22.9% of
revenue, and its five largest customers represented 15.8% of revenue. Those same
customers represented 26.7%, 17.8% and 13.6%, respectively, of total revenue for
the year ended December 31, 1995. Most of the Company's contracts with customers
are cancelable on 30 days' notice and the penalties for a shipper for breach of
contract are minimal. The loss of any of its major customers could have a
material adverse effect on the Company's operating results and profitability.
See "Business -- Marketing and Customers."
    
 
   
CAPITAL REQUIREMENTS
    
 
   
     The trucking industry and the vessels utilized to move truckload freight
require extensive investment in revenue equipment. The Company historically has
relied upon vessel charters, debt and equipment leases to finance revenue
equipment, and it has granted its lenders liens on substantially all of its
assets. If in the future the Company were unable to borrow sufficient funds,
enter into acceptable lease arrangements, sell or trade its used equipment at
acceptable prices, or raise additional equity capital, the resulting capital
shortage would limit the Company's growth and force the Company to operate its
revenue equipment for longer periods, which would be likely to adversely affect
the Company's growth and profitability. See "Use of Proceeds," "Capitalization,"
and "Management's Discussion and Analysis of Financial Condition and Results of
Operations -- Liquidity and Capital Resources."
    
 
VOTING CONTROL OF THE COMPANY
 
   
     Upon completion of the offering, Malcom P. McLean and Clara L. McLean will
beneficially own approximately 71% of all of the outstanding shares of Common
Stock. Accordingly, Malcom P. McLean and Clara L. McLean will have the ability
to elect the entire Board of Directors of the Company, determine the outcome of
all matters involving a stockholder vote, and take certain actions by written
consent with notice to the other stockholders. See "Principal Stockholders" and
"Description of Capital Stock."
    
 
RESTRICTION ON FOREIGN OWNERSHIP AND POSSIBLE REQUIRED DIVESTITURE OF STOCK
 
   
     In order to maintain the eligibility of the Company to own and operate
vessels in the U.S. domestic trade, 75% of the outstanding capital stock and
voting power of the Company is required to be held by U.S. citizens. Although
the Company's Certificate of Incorporation contains provisions limiting
non-citizenship ownership of its capital stock, the Company could lose its
ability to conduct operations in the U.S. domestic trade if such provisions
prove unsuccessful in maintaining the required level of citizen ownership. Such
loss would have a material adverse effect on the Company. If the Company
determines that persons who are not citizens of the U.S. own more than 24.99% of
the Company's outstanding capital stock or more than 24.99% of the voting power
of the Company,
    
 
                                       12
<PAGE>   14
 
   
the Company may redeem such stock or, if redemption is not permitted by
applicable law or the Board of Directors, in its discretion, elects not to make
such redemption, the Company may require the non-citizens who most recently
acquired shares to divest such excess shares to persons who are U.S. citizens in
such manner as the Board of Directors directs. The required redemption would be
at a price equal to the average closing price during the preceding 30 trading
days, which price could be materially different from the current price of the
Common Stock or the price at which the non-citizen acquired the Common Stock. If
a non-citizen purchases the Common Stock, there can be no assurance that he will
not be required to divest the shares and such divestiture could result in a
material loss. See "Description of Capital Stock -- Foreign Ownership
Restrictions."
    
 
LIMITATIONS ON TAKEOVERS
 
   
     Certain corporate governance and statutory provisions may inhibit changes
in control of the Company. Applicable provisions of Delaware law restrict the
ability of certain acquirers to engage in un-approved business combinations with
the Company. The Company's Certificate of Incorporation permits the issuance of
additional shares of authorized but unissued Common Stock and allows the Board
of Directors to establish all relevant provisions of and issue up to 1,000,000
shares of preferred stock without further action by the stockholders. Such
preferred stock could be used, for example, in a stockholder rights plan. See
"Description of Capital Stock." In addition, Malcom P. McLean and Clara L.
McLean beneficially own stock entitled to a majority of the voting power of all
of the Company's outstanding Common Stock. The effect of these provisions and
the concentration of stock ownership could be to make a takeover more difficult
or to discourage a person from attempting a takeover, including a takeover that
some stockholders may deem to be in their best interests.
    
 
SHARES ELIGIBLE FOR FUTURE SALE
 
   
     Sales of a substantial number of shares of Common Stock or the availability
of such shares for sale in the public market following the offering may
adversely affect prevailing market prices for the Common Stock and may make it
more difficult for the Company to sell its equity securities in the future on
terms it deems acceptable. Upon completion of the offering, the Company will
have 9,372,500 shares of outstanding Common Stock. All 2,700,000 shares of
Common Stock offered hereby will be freely tradable without restriction. The
remaining 6,672,500 shares owned by existing stockholders will be eligible for
sale under Rule 144 of the Securities Act of 1933 (the "Securities Act")
beginning 180 days after the date of this Prospectus.
    
 
LACK OF DIVIDENDS
 
   
     After the closing of the offering, the Company intends to retain its
earnings to finance the growth and development of its business and does not
anticipate paying cash dividends. Any payment of cash dividends in the future
will depend upon the Company's financial condition, capital requirements,
earnings, restrictions under loan agreements and other factors the Board of
Directors may deem relevant. See "Dividend Policy."
    
 
NO PRIOR PUBLIC MARKET FOR COMMON STOCK; DETERMINATION OF OFFERING PRICE
 
   
     Prior to the offering, there has been no public market for the Common
Stock, and there can be no assurance that an active trading market will develop
or, if developed, that such market will be sustained or that the stock will
trade at or above the initial public offering price. The initial public offering
price of the Common Stock offered hereby will be determined by negotiation
between the Company and the Underwriters and may bear no relationship to the
price at which the Common Stock will trade after completion of the offering. See
"Underwriting" for a discussion of the factors to be considered in determining
the initial public offering price. In addition, from time to time the stock
market experiences price and volume volatility, which may affect the market
price of the Common Stock for reasons unrelated to the Company's performance.
    
 
                                       13
<PAGE>   15
 
DILUTION
 
   
     Purchasers of Common Stock in the offering will incur immediate and
substantial dilution in net tangible book value of $8.96 per share. See
"Dilution."
    
 
                              S CORPORATION STATUS
 
     Since January 1, 1992, the Company has been treated as an S Corporation
under the Internal Revenue Code and the laws of the states that recognize S
Corporation status. Accordingly, the Company's net income was reported by and
taxed directly to the Company's stockholders rather than to the Company. The
Company's S Corporation status will terminate with the closing of the offering,
and in future periods the Company will be subject to federal and state taxes at
applicable rates. The termination of the Company's S Corporation status will
result in a one-time, non-cash charge to the Company (that would have been
approximately $650,000 at March 31, 1997) in recognition of deferred income
taxes.
 
                                USE OF PROCEEDS
 
   
     The net proceeds to the Company from the sale of the 2,700,000 shares of
Common Stock offered hereby are estimated to be approximately $29.8 million
(assuming an initial public offering price of $12.00 per share), after deducting
underwriting discounts, commissions and estimated expenses of the offering.
    
 
   
     Approximately $13.2 million of the net proceeds will be used to purchase
revenue equipment scheduled for delivery in late 1997 and early 1998. The
revenue equipment includes the 53' containers and chassis units that will be
utilized with the two Triplestack Box Carriers(TM) now being constructed to
expand the Company's service in the Puerto Rico traffic lane. Approximately $6.2
million of the net proceeds will be used to repay debt due to Kadampanattu
Corp., which is wholly owned by Malcom P. McLean, the Company's principal
stockholder. An additional $6.0 million will be used to fund the payment of an S
Corporation dividend to existing stockholders. The debt to be repaid bears
interest at 8.0% per annum and matures on December 31, 1997. Approximately $1.5
million of such debt was incurred in 1997 to fund the Company's 12.5% down
payment on the construction of two Triplestack Box Carriers(TM). Approximately
$2.2 million of the net proceeds will be used to fund the required 12.5% down
payment on three additional Triplestack Box Carriers(TM), which is currently
expected to be made in the third quarter of 1997. The approximately $2.2 million
of remaining proceeds will be used for working capital and general corporate
purposes.
    
 
     Pending application of the net proceeds as described above, the Company
intends to invest such proceeds in short-term, investment grade,
interest-bearing securities.
 
                                DIVIDEND POLICY
 
   
     The Company currently intends to retain its earnings to finance the growth
and development of its business and does not anticipate paying cash dividends.
Any payment of cash dividends in the future will depend upon the Company's
financial condition, capital requirements, earnings, restrictions under loan
agreements and other factors the Board of Directors may deem relevant.
    
 
   
     As an S Corporation, the Company has paid dividends to its stockholders
from time to time in part to partially fund or offset their tax liability with
respect to S Corporation earnings. See "S Corporation Status." Since the
Company's inception, it has paid aggregate dividends of $2.6 million. The
Company also intends to pay an S Corporation dividend of $6.0 million to its
existing stockholders with a portion of the net proceeds of the offering.
    
 
                                       14
<PAGE>   16
 
                                 CAPITALIZATION
 
   
     The following table sets forth the current portion of long-term debt,
capital lease obligations, due to affiliate and capitalization of the Company as
of March 31, 1997 (i) on an actual basis after giving retroactive effect to the
stock split and related increase in authorized capital stock in connection with
this offering, (ii) on a pro forma basis to give effect to the contemplated $6.0
million S Corporation dividend to existing stockholders, and (iii) on a pro
forma basis as adjusted to give effect to the application of the net proceeds
from the sale of the 2,700,000 shares of Common Stock pursuant to this offering
(at an assumed offering price of $12.00 per share) as set forth in "Use of
Proceeds":
    
 
   
<TABLE>
<CAPTION>
                                                                MARCH 31, 1997
                                                       ---------------------------------
                                                                              PRO FORMA
                                                       ACTUAL    PRO FORMA   AS ADJUSTED
                                                       -------   ---------   -----------
                                                                (IN THOUSANDS)
<S>                                                    <C>       <C>         <C>
Current portion of long-term debt and capital lease
  obligations........................................  $ 2,902    $2,902       $ 2,902
Due to affiliate.....................................    5,878     5,878            --
                                                       -------    ------       -------
                                                       $ 8,780    $8,780       $ 2,902
                                                       =======    ======       =======
 
Long-term debt and capital lease obligations (net of
  current portion)...................................  $ 6,462    $6,462       $ 6,462
Stockholders' equity:
  Preferred stock: $.01 par value, 1,000,000 shares
     authorized, no shares outstanding...............       --        --            --
  Common Stock, $.01 value, 20,000,000 shares
     authorized; 6,672,500 shares issued and
     outstanding, 9,372,500 shares issued and
     outstanding as adjusted(1)......................       67        67            94
Additional paid-in capital...........................      (67)      (67)       29,706
Retained earnings....................................    6,314       314          (336)(2)
                                                       -------    ------       -------
     Total stockholders' equity......................    6,314       314        29,464(2)
                                                       -------    ------       -------
          Total capitalization.......................  $12,776    $6,776       $35,926
                                                       =======    ======       =======
</TABLE>
    
 
- ---------------
 
   
(1) Excludes 785,000 shares of Common Stock reserved for issuance to employees
    under the Company's Incentive Stock Plan (of which options to purchase
    471,000 shares at the initial public offering price have been granted). See
    "Management -- Incentive Stock Plan."
    
   
(2) Reflects a non-cash charge (that would have been $650,000 at March 31, 1997)
    that will result from the termination of the Company's S Corporation status.
    See Note 3 to the Financial Statements.
    
 
                                       15
<PAGE>   17
 
                                    DILUTION
 
   
     The net tangible book value of the Company's Common Stock as of March 31,
1997 was approximately $5.4 million, or $.81 per share. Net tangible book value
per share represents the amount of the Company's stockholders' equity, less
intangible assets (consisting of goodwill), divided by 6,672,500 shares of
Common Stock outstanding.
    
 
   
     Net tangible book value dilution per share represents the difference
between the amount per share paid by purchasers of shares of Common Stock in the
offering made hereby and the pro forma net tangible book value per share of
Common Stock immediately after completion of the offering. After giving effect
to (i) the sale of 2,700,000 shares of Common Stock in the offering at an
assumed price of $12.00 per share, (ii) the application of the estimated net
proceeds therefrom, and (iii) the non-cash charge (that would have been $650,000
at March 31, 1997) in recognition of deferred income taxes as described in "S
Corporation Status," the pro forma net tangible book value of the Company as of
March 31, 1997, would have been $28.5 million, or $3.04 per share. This
represents an immediate increase in net tangible book value of $2.34 per share
to existing stockholders and an immediate dilution in pro forma net tangible
book value of $8.96 per share to purchasers of shares of Common Stock in the
offering, as illustrated in the following table:
    
 
   
<TABLE>
<S>                                                           <C>     <C>
Assumed public offering price per share.....................          $12.00
  Net tangible book value per share at March 31, 1997.......  $ .81
  Pro forma non-cash adjustment to recognize deferred income
     taxes..................................................   (.10)
  Increase per share attributable to new investors..........   2.34
Pro forma net tangible book value per share after the
  offering..................................................            3.04
                                                                      ------
Net tangible book value dilution per share to new
  investors.................................................          $ 8.96
                                                                      ======
</TABLE>
    
 
   
     The following table sets forth as of March 31, 1997 the difference between
existing stockholders and the purchasers of shares in the offering (at an
assumed offering price of $12.00 per share) with respect to the number of shares
purchased from the Company, the total consideration paid, and the average price
per share paid:
    
 
   
<TABLE>
<CAPTION>
                                         SHARES PURCHASED      TOTAL CONSIDERATION
                                        -------------------   ---------------------   AVERAGE PRICE
                                         NUMBER     PERCENT     AMOUNT      PERCENT     PER SHARE
                                        ---------   -------   -----------   -------   -------------
<S>                                     <C>         <C>       <C>           <C>       <C>
Existing stockholders.................  6,672,500     71.2%   $       425       --%      $   --
New investors.........................  2,700,000     28.8%    32,400,000    100.0%      $12.00
                                        ---------    -----    -----------    -----
          Total.......................  9,372,500    100.0%   $32,400,425    100.0%
                                        =========    =====    ===========    =====
</TABLE>
    
 
                                       16
<PAGE>   18
 
                     SELECTED FINANCIAL AND OPERATING DATA
 
   
     The selected financial data set forth below has been derived from the
financial statements of the Company. The financial statements as of December 31,
1995 and 1996 and for each of the three years in the period ended December 31,
1996 have been audited by Deloitte & Touche LLP, independent auditors, and such
financial statements and the report thereon are included in this Prospectus. The
financial statements as of December 31, 1992, 1993 and 1994 and for each of the
two years in the period ended December 31, 1993 have also been audited and are
not included herein. The financial statements as of March 31, 1996 and 1997 and
for the three months then ended are unaudited. However, in the opinion of
management, all adjustments of a normal recurring nature which are necessary to
present a fair statement of the results for the interim periods have been made.
The unaudited results of operations for the interim periods are not necessarily
indicative of the results for the full year. The selected financial information
set forth below should be read in conjunction with "Management's Discussion and
Analysis of Financial Condition and Results of Operations" and the Financial
Statements appearing elsewhere in this Prospectus, including the notes thereto.
    
 
   
<TABLE>
<CAPTION>
                                                                                                      Three Months
                                                                                                          Ended
                                                          Year Ended December 31,                       March 31,
                                            ----------------------------------------------------   -------------------
                                              1992       1993       1994       1995     1996(1)    1996(1)      1997
                                            --------   --------   --------   --------   --------   --------   --------
                                                   (In thousands, except per share amounts and operating data)
<S>                                         <C>        <C>        <C>        <C>        <C>        <C>        <C>
STATEMENT OF OPERATIONS DATA:
  Operating revenues......................  $ 38,778   $ 67,613   $ 72,192   $ 62,531   $ 63,148   $ 14,568   $ 16,446
  Operating expenses:
    Salaries, wages and benefits..........    10,443     15,831     19,307     14,592     13,289      3,435      3,404
    Rent and purchased transportation.....    17,320     23,398     19,616     14,497     16,231      3,430      4,211
    Fuel..................................     3,440      4,240      5,429      5,256      5,883      1,468      1,557
    Operations and maintenance............     7,512      9,192     11,781     10,553     14,211      3,046      3,206
    Taxes and licenses....................       392        989        960        589        455        138        156
    Insurance and claims..................     1,331      2,051      2,202      1,861      2,121        514        522
    Communications and utilities..........       631        824        834        621        608        143        134
    Depreciation and amortization.........     1,418      1,370      2,647      2,761      2,944        701        689
    Other operating expenses..............     5,600      4,624      3,241      3,023      2,981        727        819
                                            --------   --------   --------   --------   --------   --------   --------
        Total operating expenses..........    48,087     62,519     66,017     53,753     58,723     13,602     14,698
                                            --------   --------   --------   --------   --------   --------   --------
  Operating income (loss).................    (9,309)     5,094      6,175      8,778      4,425        966      1,748
  Interest expense, net...................      (864)    (1,384)    (1,817)    (1,362)    (1,082)      (247)      (264)
  Gain (loss) on sale of equipment........        --        440         12         48         67         (9)        --
                                            --------   --------   --------   --------   --------   --------   --------
        Total nonoperating expense, net...      (864)      (944)    (1,805)    (1,314)    (1,015)      (256)      (264)
                                            --------   --------   --------   --------   --------   --------   --------
  Income (loss) before provision and pro
    forma provision (benefit) for income
    taxes.................................   (10,173)     4,150      4,370      7,464      3,410        710      1,484
  Provision for income taxes..............        --          9         12         67         39          8         29
                                            --------   --------   --------   --------   --------   --------   --------
  Income (loss) before pro forma provision
    (benefit) for income taxes............   (10,173)     4,141      4,358      7,397      3,371        702      1,455
  Pro forma provision (benefit) for income
    taxes(2)..............................    (3,860)     1,615      2,015      3,037      1,298        259        546
                                            --------   --------   --------   --------   --------   --------   --------
  Pro forma net income (loss)(2)..........  $ (6,313)  $  2,526   $  2,343   $  4,360   $  2,073   $    443   $    909
                                            ========   ========   ========   ========   ========   ========   ========
  Pro forma net income per common
    share(3)..............................                                              $    .29              $    .13
                                                                                        ========              ========
  Pro forma weighted average shares
    outstanding(3)........................                                                 7,173                 7,173
  Supplementary pro forma net income per
    common share(4).......................                                              $    .30              $    .12
OPERATING DATA:
  Operating ratio(5)......................     124.0%      92.5%      91.4%      86.0%      93.0%      93.4%      89.4%     
  Vessel utilization outbound.............      60.1%      93.5%      90.9%      96.0%      88.4%(6)   96.3%      78.1%(6)  
  Vessel utilization inbound..............      12.1%      36.6%      52.8%      51.6%      42.0%(6)   59.8%      33.6%(6)  
  Overall vessel capacity utilization.....      36.1%      65.0%      71.8%      73.8%      65.3%(6)   78.1%      55.8%(6)  
  Tractor loaded mile percentage..........      77.3%      87.1%      86.2%      81.0%      81.5%      83.0%      80.5%
  Weighted average tractors...............       178        199        256        187        163        174        154
  Weighted average trailers...............       923      1,629      1,605      1,458      1,762      1,400      1,983
</TABLE>
    
 
                                       17
<PAGE>   19
 
   
<TABLE>
<CAPTION>
                                                                December 31,                            March 31,
                                            ----------------------------------------------------   -------------------
                                              1992       1993       1994       1995     1996(1)    1996(1)      1997
                                            --------   --------   --------   --------   --------   --------   --------
                                                   (In thousands, except per share amounts and operating data)
<S>                                         <C>        <C>        <C>        <C>        <C>        <C>        <C>
BALANCE SHEET DATA:
  Working capital deficit.................  $(16,867)  $(13,174)  $(10,188)  $ (4,697)  $ (1,719)  $ (3,712)  $ (2,823)
  Net property and equipment..............     3,366      9,428     11,118      8,851     12,512      8,189     14,349
        Total assets......................    13,816     20,688     23,521     20,226     24,764     18,557     26,440
  Long-term debt, capitalized leases and
    due to affiliate(7)...................    15,322     22,771     20,776     13,461     13,879     11,085     15,242
  Stockholders' equity (deficit)..........   (11,356)    (7,214)    (2,856)     2,673      6,045      3,376      6,314
</TABLE>
    
 
- ---------------
 
   
(1) During 1996, each of the Company's barge vessels was increased in size
    through a mid-body expansion program that resulted in a 56% increase in
    vessel capacity and was accomplished over a six-month period. From
    mid-February through mid-July 1996, only one of the Company's vessels was in
    service at a time. To maintain weekly service frequency, a smaller
    substitute vessel was utilized, resulting in both reduced revenue and
    additional costs. For these reasons, management believes that overall 1996
    results are not indicative of the results that would be expected had both of
    the Company's vessels remained in service throughout the year.
    
   
(2) Since January 1, 1992, the Company has operated as an S Corporation under
    the Internal Revenue Code and the laws of the states that recognize S
    Corporation status. As a result, the Company's taxable earnings were taxed
    directly to the Company's then-existing stockholders. Pro forma net income
    assumes that the Company was subject to federal and state income taxes and
    was taxed as a C Corporation at the effective tax rates that would have
    applied for all periods. See Note 2 to the Financial Statements. With the
    closing of the offering, the Company will become subject to federal and
    state income taxes. The pro forma statement of operations data do not give
    effect to a non-cash charge (that would have been approximately $650,000 at
    March 31, 1997) in recognition of deferred income taxes that will result
    from the termination of the Company's S Corporation status upon
    effectiveness of the offering.
    
   
(3) Pro forma net income per share reflects a 15,700-for-1 stock split that will
    become effective in connection with the offering and the issuance of 500,000
    shares of Common Stock to fund the payment of a $6.0 million S Corporation
    dividend to existing stockholders with a portion of the net proceeds of the
    offering.
    
   
(4) The Company expects to use a portion of the net proceeds from the offering
    to repay amounts due to affiliate. Supplementary pro forma net income per
    share reflects the interest savings and the issuance of approximately
    652,000 shares of Common Stock to fund the repayment, assuming the issuance
    and repayment had occurred on January 1, 1996.
    
   
(5) Operating expenses as a percentage of revenue.
    
   
(6) From mid-February through mid-July 1996, only one of the Company's two
    vessels was in service at a time due to the Company's mid-body expansion
    program, and the Company operated during this period with a second, smaller
    substitute vessel. Vessel capacity outbound to Puerto Rico and inbound to
    the U.S. increased from 266 48' trailer equivalents at February 1, 1996 to
    416 48' trailer equivalents at July 31, 1996.
    
   
(7) Includes current maturities.
    
 
                                       18
<PAGE>   20
 
               MANAGEMENT'S DISCUSSION AND ANALYSIS OF FINANCIAL
                      CONDITION AND RESULTS OF OPERATIONS
 
OVERVIEW
 
   
     Trailer Bridge was incorporated in 1991. In February 1992, the Company
commenced integrated truckload and marine services between the U.S. and Puerto
Rico utilizing high-cube truckload equipment and two ocean-going barges. The
Company generates revenue by providing integrated truckload and marine freight
transportation between Puerto Rico and points within the continental U.S.
("Puerto Rico revenue") and to a lesser extent by providing truckload freight
transportation between points within the continental U.S. ("non-Puerto Rico
revenue"). In April 1992, Trailer Bridge acquired a Midwestern truckload carrier
with significant non-Puerto Rico revenue, primarily to increase the size of the
Company's truckload fleet. Starting in late 1994, Trailer Bridge began to
increase its focus on serving marine related markets by reducing inland
truckload service in traffic lanes which were not complementary to lanes serving
Puerto Rico freight customers.
    
 
     The table below reflects Puerto Rico revenue, non-Puerto Rico revenue and
total revenue for the three years ended December 31, 1996 and the three months
ended March 31, 1996 and 1997:
 
   
<TABLE>
<CAPTION>
                                                                                               THREE MONTHS ENDED
                                           YEAR ENDED DECEMBER 31,                                  MARCH 31,
                          ---------------------------------------------------------   -------------------------------------
                                1994                1995                1996                1996                1997
                          -----------------   -----------------   -----------------   -----------------   -----------------
                          AMOUNT    PERCENT   AMOUNT    PERCENT   AMOUNT    PERCENT   AMOUNT    PERCENT   AMOUNT    PERCENT
                          -------   -------   -------   -------   -------   -------   -------   -------   -------   -------
                                                               (Dollars in thousands)
<S>                       <C>       <C>       <C>       <C>       <C>       <C>       <C>       <C>       <C>       <C>
Puerto Rico.............  $50,829     70.4%   $53,167     85.0%   $56,347     89.2%   $12,638     86.8%   $15,378     93.5%
Non-Puerto Rico.........   21,363     29.6      9,364     15.0      6,801     10.8      1,930     13.2      1,068      6.5
                          -------    -----    -------    -----    -------    -----    -------    -----    -------    -----
Total...................  $72,192    100.0%   $62,531    100.0%   $63,148    100.0%   $14,568    100.0%   $16,446    100.0%
                          =======    =====    =======    =====    =======    =====    =======    =====    =======    =====
</TABLE>
    
 
   
     During 1996, each of the Company's barge vessels was increased in size
through a mid-body expansion program that resulted in a 56% increase in vessel
capacity and was accomplished over a six-month period. From mid-February through
mid-July 1996, only one of the Company's vessels was in service at a time. To
maintain weekly service frequency, a smaller substitute vessel was utilized,
resulting in both reduced revenue and additional costs. For these reasons,
management believes that overall 1996 results are not indicative of the results
that would be expected had both of the Company's vessels remained in service
throughout the year.
    
 
   
     The Company is in the process of compiling preliminary results for the
second quarter of 1997 and expects to report revenues of approximately $16
million for the three months ended June 30, 1997. See "-- Seasonality." In
addition, on May 21, 1997, the majority stockholder of the Company granted to
the Company's Chairman and Chief Executive Officer, an option to purchase up to
942,000 shares of Common Stock (adjusted for the 15,700-for-1 stock split) owned
by him at $.95 per share or an aggregate price of $891,330 for all shares. These
options are immediately exercisable and have a term of 10 years. In connection
with this option, the Company expects to record a nonrecurring, noncash charge
for compensation expense and a credit to paid-in capital of approximately $10.4
million in the second quarter of 1997, representing the difference between the
exercise price and an assumed initial public offering price of $12.00 per share.
This option does not involve the issuance of additional shares of Common Stock
by the Company and therefore, any subsequent purchase of shares under the option
will not have a dilutive effect on the Company's book value or earnings per
share amounts. As a result of the grant of the option, the Company will report a
significant loss in the second quarter of 1997.
    
 
                                       19
<PAGE>   21
 
RESULTS OF OPERATIONS
 
   
     The following table sets forth the percentage relationship of certain items
to operating revenues for the periods indicated:
    
 
   
<TABLE>
<CAPTION>
                                                                                 THREE MONTHS
                                                                                     ENDED
                                                      YEAR ENDED DECEMBER 31,      MARCH 31,
                                                      ------------------------   -------------
                                                       1994     1995     1996    1996    1997
                                                      ------   ------   ------   -----   -----
<S>                                                   <C>      <C>      <C>      <C>     <C>
Operating revenues.................................    100.0%   100.0%   100.0%  100.0%  100.0%
Operating expenses:
  Salaries, wages, and benefits....................     26.7     23.3     21.0    23.6    20.7
  Rent and purchased transportation................     27.2     23.2     25.7    23.6    25.6
  Fuel.............................................      7.5      8.4      9.3    10.1     9.5
  Operations and maintenance.......................     16.3     17.0     22.5    20.9    19.5
  Taxes and licenses...............................      1.3      0.9      0.7     0.9     0.9
  Insurance and claims.............................      3.1      3.0      3.4     3.5     3.2
  Communications and utilities.....................      1.2      1.0      1.0     1.0     0.8
  Depreciation and amortization....................      3.7      4.4      4.7     4.8     4.2
  Other operating expenses.........................      4.4      4.8      4.7     5.0     5.0
                                                       -----    -----    -----   -----   -----
          Total operating expenses.................     91.4     86.0     93.0    93.4    89.4
                                                       -----    -----    -----   -----   -----
Operating income...................................      8.6     14.0      7.0     6.6    10.6
Interest expense, net..............................     (2.5)    (2.2)    (1.7)   (1.7)   (1.6)
Gain (loss) on sale of equipment...................      0.0      0.1      0.1    (0.0)    0.0
                                                       -----    -----    -----   -----   -----
  Total nonoperating expense, net..................     (2.5)    (2.1)    (1.6)   (1.7)   (1.6)
Income before provision and pro forma provision for
  income taxes.....................................      6.1     11.9      5.4     4.9     9.0
Provision for income taxes.........................      0.1      0.1      0.1     0.1     0.2
                                                       -----    -----    -----   -----   -----
Income before pro forma provision for income
  taxes............................................      6.0     11.8      5.3     4.8     8.8
Pro forma provision for income taxes...............      2.8      4.8      2.0     1.8     3.3
                                                       -----    -----    -----   -----   -----
Pro forma net income...............................      3.2%     7.0%     3.3%    3.0%    5.5%
                                                       =====    =====    =====   =====   =====
</TABLE>
    
 
  Three Months Ended March 31, 1997 Compared to Three Months Ended March 31,
1996
 
   
     Operating revenues increased $1.8 million, or 12.9%, to $16.4 million
during the three months ended March 31, 1997 from $14.6 million during the year
earlier period. This increase was due to a $2.7 million (21.7%) increase in
Puerto Rico revenue through the utilization of a portion of the additional
capacity resulting from the mid-body project, partially offset by a $862,000
(44.7%) decrease in non-Puerto Rico revenue as available tractor capacity was
targeted further towards Puerto Rico revenue. Vessel capacity utilization on the
core continental U.S. to Puerto Rico traffic lane was 78.1% during the three
months ended March 31, 1997, compared to 96.3% during the year earlier period
during which a smaller substitute vessel was utilized.
    
 
   
     Salaries, wages, and benefits expense was $3.4 million for the three months
ended March 31, 1997, a decrease of $31,000 from the year earlier period due to
a reduction in drivers. As a percentage of revenue, salaries, wages and benefits
expense decreased to 20.7% during the three months ended March 31, 1997 from
23.6% for the year earlier period. This decrease was attributable to the
increased relative proportion of Puerto Rico revenue, which is not as labor
intensive as non-Puerto Rico revenue.
    
 
   
     Rent and purchased transportation expense (which includes the tug
time-charter and vessel charter paid by the Company as well as expenses related
to leasing of rolling stock) increased $781,000 from the year earlier period
primarily due to a $980,000 increase in charter fees for the expanded vessels,
partially offset by a $242,000 net reduction in rolling stock rental costs as a
result
    
 
                                       20
<PAGE>   22
 
   
of an increase in the proportion of owned as compared to leased equipment. Rent
and purchased transportation increased to 25.6% of revenue during the three
months ended March 31, 1997 compared to 23.6% of revenue during the year earlier
period as a result of the increased charter fees.
    
 
     Fuel expense as a percentage of revenue was 9.5% during the three months
ended March 31, 1997 compared to 10.1% during the year earlier period. This
decrease was primarily due to additional Puerto Rico revenue that generally has
a lower fuel cost compared to non-Puerto Rico revenue, partially offset by an
increase in average fuel prices.
 
   
     Operations and maintenance expense (which includes marine terminal rental
and cargo-handling costs) was $3.2 million for the three months ended March 31,
1997, up from $3.0 million for the year earlier period. As a percentage of
revenue, operations and maintenance expense decreased to 19.5% from 20.9% during
the year earlier period. The improvement resulted from the elimination of
temporary inefficiencies and increased per unit handling costs associated with
the use of a smaller substitute vessel during the 1996 mid-body expansion
program, partially offset by the higher operating costs associated with the
Company's expanded Puerto Rico operations.
    
 
   
     Insurance and claims expense decreased to 3.2% of revenue during the three
months ended March 31, 1997 from 3.5% of revenue during the year earlier period.
This decrease was attributable to additional Puerto Rico revenue, which
generally has a lower payroll insurance cost than non-Puerto Rico revenue.
    
 
   
     Communications and utilities expense decreased to 0.8% of revenue during
the three months ended March 31, 1997 from 1.0% of revenue during the year
earlier period. This decrease was attributable to additional Puerto Rico
revenue, which generally requires less communication and therefore has a lower
communication cost than non-Puerto Rico revenue.
    
 
   
     Depreciation and amortization expense decreased to 4.2% of revenue during
the three months ended March 31, 1997 from 4.8% of revenue during the year
earlier period. This decrease was attributable to the increased relative
significance of Puerto Rico revenue, which to date has not required the same
proportionate investment in depreciable equipment as non-Puerto Rico revenue.
Unlike the present vessels, the Triplestack Box Carriers(TM) being built in 1997
will be owned by the Company and will be depreciated by the Company.
    
 
     Other operating expense (which includes office building rent and general
supplies) was $819,000 during the three months ended March 31, 1997, compared to
$727,000 for the year earlier period. As a percentage of revenue, other
operating expense remained constant at 5.0%.
 
     The Company's operating ratio improved to 89.4% during the first quarter of
1997 from 93.4% during the year earlier period primarily as a result of the
increased Puerto Rico revenue that resulted from the Company's 1996 mid-body
expansion program, as well as a related increase in the Company's ability to use
available trucking capacity for its more profitable core Puerto Rico traffic.
 
   
     Interest expense (net) decreased slightly to 1.6% of revenue during the
three months ended March 31, 1997 due to reductions in average outstanding
balances (primarily amounts owed to an affiliate).
    
 
     As a result of the factors described above, pro forma net income more than
doubled to $909,000 (5.5% of revenue) during the three months ending March 31,
1997 from $443,000 (3.0% of revenue) during the year earlier period.
 
  Year ended December 31, 1996 Compared to Year ended December 31, 1995
 
   
     During 1996, the Company implemented an expansion program that increased
the capacity of its vessels by 56% through the insertion of a mid-body in both
of its vessels. Throughout the six-month construction period, only one of the
Company's vessels was in service along with, first, a substitute vessel
one-third smaller, followed by a substitute vessel more than two-thirds smaller
than the Company's pre-modified vessels. One of the Company's vessels was out of
service from
    
 
                                       21
<PAGE>   23
 
   
mid-February to mid-May, while the other was out of service from mid-May to
mid-July 1996. Although weekly service was maintained, the resulting
fluctuations in vessel capacity led to inefficiencies, temporary loss of
business and increased costs in all cost categories, most notably in the marine
cargo handling area.
    
 
   
     Operating revenues increased $617,000 (1.0%) to $63.1 million during 1996
from $62.5 million during 1995. This reflects a $3.2 million (6.0%) increase in
Puerto Rico revenue, substantially offset by a $2.6 million (27.4%) decrease in
non-Puerto Rico revenue. The decrease in non-Puerto Rico revenue resulted from a
shift in the Company's business away from domestic traffic lanes which were not
complementary to Puerto Rico traffic lanes and a decrease in the average length
of domestic hauls.
    
 
   
     Salaries, wages and benefits expense decreased slightly to $13.3 million
during 1996 from $14.6 million for 1995, and decreased as a percentage of
revenue to 21.0% during 1996 from 23.3% during 1995. This decrease as a
percentage of revenues was attributable to the shift away from non-Puerto Rico
domestic traffic lanes, resulting in a reduction in the number of truck drivers
employed by the Company.
    
 
   
     Rent and purchased transportation expense increased $1.7 million to $16.2
million due to a $2.2 million increase in charter fees on the enlarged vessels,
partially offset by a $500,000 decrease in rolling stock rental expense. As a
percentage of revenue, rent and purchased transportation expense increased to
25.7% during 1996 compared to 23.2% during 1995. Such increase was primarily due
to (i) the increase in post-modification barge charter fees, and (ii) the
Company's payment of pre-modification charter fees during the mid-body project
while using smaller capacity substitute vessels. While the Company's larger
roll-on/roll-off barges were undergoing renovations, the Company leased smaller
substitute barges from a third party and incurred $1.2 million of additional
barge rent and $500,000 of other transitional expenses, which were reimbursed by
the charterer of the roll-on/roll-off vessels. Accordingly, there was not a net
increase in the aggregate rental expense attributable to the substitute vessels.
    
 
     Fuel expense increased $627,000 to $5.9 million and increased to 9.3% of
revenue during 1996 from 8.4% of revenue during 1995, primarily due to an
increase in average fuel prices.
 
   
     Operations and maintenance expense increased $3.6 million to $14.2 million
in 1996 from $10.6 million in 1995. Operations and maintenance expense increased
as a percentage of revenue to 22.5% during 1996 from 17.0% during 1995. These
increases were attributable to an increase in cargo handling costs related to
the complexity of loading substitute vessels during the mid-body modification
project.
    
 
   
     Taxes and licenses expense decreased to .7% of revenue during 1996 compared
to .9% of revenue during 1995. This decrease resulted from a reduction in
non-Puerto Rico revenue which has a higher tax and license cost (primarily
highway taxes and local taxes and licenses) than Puerto Rico revenue.
    
 
   
     Insurance and claims expense increased to 3.4% of revenue during 1996 from
3.0% of revenue during 1995. This increase was attributable to increased cargo
claims due to the use of smaller substitute vessels during the mid-body
modification project and increased insurance levels related to a higher
concentration of owned revenue equipment and the higher replacement cost of the
enlarged vessels.
    
 
   
     Depreciation and amortization expense increased to $2.9 million, or 4.7% of
revenue, during 1996 from $2.8 million, or 4.4% of revenue, during 1995. This
increase resulted from increases in owned trailers, some of which replaced
trailers utilized under operating leases, partially offset by a reduction in
owned tractors which were previously utilized in the non-Puerto Rico traffic
lanes.
    
 
   
     Other operating expense remained flat at $3.0 million during 1995 and 1996.
There was a slight decrease in other operating expense as a percentage of
revenue to 4.7% for 1996 from 4.8% for 1995.
    
 
                                       22
<PAGE>   24
 
   
     The Company's operating ratio increased to 93.0% during 1996 from 86.0%
during 1995 primarily as a result of the midbody expansion project and
inefficiencies related to the substitute vessels, including increased labor and
cargo handling fees and use of specialized equipment, temporary loss of business
and increased charter fees for the expanded vessels.
    
 
   
     Interest expense (net) decreased to $1.1 million, or 1.7% of revenue,
during 1996 from $1.4 million, or 2.2% of revenue, during 1995 due to reductions
in average outstanding balances (primarily amounts owed to an affiliate).
    
 
     As a result of the factors described above, pro forma net income decreased
52.5% to $2.1 million (3.3% of revenue) during 1996 from $4.4 million (7.0% of
revenue) during 1995.
 
  Year ended December 31, 1995 Compared to Year ended December 31, 1994
 
   
     During 1995, the Company continued to tailor its non-Puerto Rico revenue
services to its core Puerto Rico traffic lanes. As a result, many of the traffic
lanes previously served by a truckload carrier acquired in 1992 which did not
complement the Company's continental U.S. to Puerto Rico traffic lanes were
eliminated, and non-Puerto Rico trucking revenue decreased 56.2% to $9.4 million
in 1995 from $21.4 million in 1994.
    
 
   
     Operating revenues decreased 13.4% to $62.5 million during 1995 from $72.2
million during 1994 as a direct result of a $12.0 million, or 56.2%, reduction
in non-Puerto Rico revenue, partially offset by a $2.3 million increase in
Puerto Rico revenue. Overall, Puerto Rico revenue increased 4.6% in 1995
compared to 1994.
    
 
   
     Salaries, wages and benefits expense decreased $4.7 million to $14.6
million, or 23.3% of revenue, during 1995 from $19.3 million, or 26.7% of
revenue, during 1994. This decrease was primarily attributable to the reduction
in non-Puerto Rico revenue and the related reduction in the number of drivers
employed by the Company, primarily owner-operators.
    
 
   
     Rent and purchased transportation expense was $14.5 million, or 23.2% of
revenue, during 1995 compared to $19.6 million, or 27.2% of revenue, during
1994. This decrease resulted from a reduction in the number of owner-operator
tractors due to the reduction in non-Puerto Rico revenue.
    
 
     Although fuel expense decreased slightly to $5.3 million in 1995 from $5.4
million in 1994, it increased to 8.4% of revenue in 1995 compared to 7.5% of
revenue in 1994 due to the reduction in the number of owner-operator tractors,
whose fuel cost is included in rent and purchased transportation.
 
   
     Operations and maintenance expense decreased to $10.6 million in 1995 from
$11.8 million in 1994, primarily due to a reduction in the number of
owner-operators. Operations and maintenance expense as a percentage of revenue
increased to 17.0% in 1995 from 16.3% in 1994, reflecting a higher proportion of
Puerto Rico revenue and its related cargo handling expense.
    
 
   
     Taxes and licenses expense decreased to .9% of revenue during 1995 from
1.3% of revenue during 1994. This decrease was attributable to the reduction in
non-Puerto Rico revenue, which generally has a higher tax and license cost than
Puerto Rico revenue.
    
 
   
     Insurance and claims expense decreased to 3.0% of revenue during 1995 from
3.1% of revenue during 1994. This decrease was attributable to the reduction in
non-Puerto Rico revenue, which generally has a higher insurance cost than Puerto
Rico revenue.
    
 
   
     Communications and utilities expense decreased to 1.0% of revenue during
1995 from 1.2% during 1994. This decrease was attributable to the lower level of
non-Puerto Rico revenue, which generally requires more communication and
therefore has a higher communication cost than Puerto Rico revenue.
    
 
                                       23
<PAGE>   25
 
   
     Depreciation and amortization expense increased to $2.8 million, or 4.4% of
revenue, during 1995 from $2.6 million, or 3.7% of revenue, during 1994 as a
result of purchases of both tractor and trailer equipment and a reduction in
non-Puerto Rico revenue.
    
 
     Other operating expenses increased to 4.8% of revenue in 1995 from 4.4% of
revenue in 1994 due to a non-recurring expense for the off-hire of equipment
utilized in domestic traffic lanes which were not complementary to Puerto Rico
traffic lanes.
 
     The Company's operating ratio improved to 86.0% in 1995 from 91.4% during
1994 primarily as a result of elimination of non-Puerto Rico traffic lanes and
increase in Puerto Rico revenue.
 
   
     Interest expense (net) decreased to $1.4 million, or 2.2% of revenue,
during 1995 from $1.8 million, or 2.5% of revenue, during 1994 due to reductions
in outstanding average balances (primarily amounts owed to an affiliate).
    
 
   
     As a result of the factors described above, pro forma net income increased
86.1% to $4.4 million (7.0% of revenue) in 1995 from $2.3 million (3.2% of
revenue) during 1994.
    
 
LIQUIDITY AND CAPITAL RESOURCES
 
   
     The growth of the Company's business has required significant investment in
revenue equipment that the Company historically has financed with charters,
borrowings under installment notes payable to commercial lending institutions
and equipment leases from third-party lessors. The Company's primary sources of
liquidity historically have been funds provided by operations, borrowings,
leases with financial institutions and financial support from an affiliate.
    
 
   
     At March 31, 1997, working capital was negative $2.8 million, which
reflects $5.8 million due to an affiliate that will be repaid from the net
proceeds of the offering. The Company expects that in future years it will
continue to finance substantially all revenue equipment additions through
borrowing or leasing transactions. Management also expects that the offering and
its effect on the Company's capitalization will enable Trailer Bridge to finance
revenue equipment on more favorable terms than those obtained in the past. The
Company currently has a line of credit from a financial institution for up to
$7.1 million to fund the replacement of 125 tractors, the material terms of
which are described below. At March 31, 1997, approximately $1.1 million was
utilized under this line of credit, which is secured by the purchased tractors.
The interest rate on amounts outstanding under the line of credit is 1.40% above
the financial institution's three-year cost of funds in effect from time to time
(7.98% at March 31, 1997). The Company may elect different interest accrual
options for future borrowings under the line of credit (see Note 7 to the
Financial Statements). The Company had outstanding long-term debt, capitalized
lease obligations and due to affiliate (including current portions) of
approximately $15.2 million at March 31, 1997, most of which comprised
obligations for the purchase of revenue equipment. See Notes 6 and 7 to the
Financial Statements.
    
 
   
     Net cash provided by operating activities was $7.2 million in 1996,
compared to $8.1 million in 1995. The difference between the Company's 1996 cash
flow and its $3.4 million in net income was primarily attributable to $3.0
million of depreciation, a $674,000 provision for bad debt and a $659,000
increase in payables. The Company's operating cash flow of $2.9 million during
the first quarter of 1997 reflects $690,000 of depreciation, a $620,000 decrease
in prepaid expenses, and a $590,000 increase in accrued liabilities, partially
offset by a $620,000 decrease in accounts payable.
    
 
   
     Net cash used in investing activities was $9.5 million in 1996 compared to
$5.0 million in 1995. The Company's 1996 cash flow reflects $6.7 million of
capital expenditures and $3.2 million of repayments of debt to an affiliate. Net
cash used in investing activities in the first quarter of 1997 reflects $2.5
million of capital expenditures, which was primarily attributable to the
down-payment on the Company's two new Triplestack Box Carriers(TM) as well as
the purchase of revenue equipment.
    
 
     Net cash provided by financing activities was $3.4 million in 1996,
compared to $4.5 million of net cash used in financing activities in 1995. The
Company's 1996 cash flow reflects increased
 
                                       24
<PAGE>   26
 
   
borrowings to finance the Company's capital expenditure program. Net cash
provided by financing activities for the first quarter of 1997 reflects $1.2
million in dividends.
    
 
   
     The Company expects vessel and equipment purchases to total approximately
$32.3 million in 1997, of which $12.0 million will be used for new vessel
purchases, $13.2 million for related container and chassis equipment additions
and $7.1 million for replacement tractors. The Company's projected capital
expenditures for its new Triplestack Box Carriers(TM) have been funded with a
12.5% down-payment ($1.5 million) from working capital advanced by the Company's
affiliate and to be repaid out of the proceeds of this offering. The 87.5%
remaining balance will be funded from the escrowed proceeds of a Title XI bond
offering completed in June 1997. The Title XI bonds require equal semi-annual
principal payments over a 25 year term and bear interest at a rate of 7.07% per
annum. The approximately $13.2 million in 53' container and chassis equipment
for the new vessels will be funded from the net proceeds of this offering. See
"Use of Proceeds." The Company's $7.1 million tractor replacement program will
be funded through the sale of used tractors and the line of credit described
above.
    
 
   
     During 1997, the Company will complete the construction of a new office
building adjacent to its Jacksonville truck terminal that will centralize all
Jacksonville administrative personnel. The remaining cost of the office building
will be funded with escrowed proceeds from an existing mortgage and cash flows
from operations.
    
 
   
     The Company has a pending application with the U.S. Maritime Administration
for a Title XI guaranty commitment to finance 87.5% of the construction costs of
an additional three Triplestack Box Carriers(TM) which the Company intends to
utilize in the coastwise traffic lanes. The required $2.2 million down payment,
which is expected to be funded in the third quarter of 1997, will be funded from
the net proceeds of this offering. The Company anticipates that, subsequent to
this offering, it will obtain a formal Title XI commitment from the U.S.
Maritime Administration similar to that obtained in connection with the first
two Triplestack Box Carriers(TM). Construction of those vessels will then
commence immediately under the Company's fixed-priced contract with Halter
Marine Group, Inc. The initial vessel is expected to be delivered seven months
after construction commences, with additional vessels to follow in two month
increments. Trailer Bridge intends to finance the approximately $17.7 million in
container and chassis equipment needed in 1998 for these three Triplestack Box
Carriers(TM) under existing proposals it has received from financial
institutions.
    
 
     The Company utilizes tugs, terminals, office space, certain trailers and
miscellaneous equipment under a number of operating leases, some of which
include labor and other cost items. The minimum expected payment under all of
these operating leases is $16.1 million in 1997, including $7.6 million due an
affiliate for charter of existing vessels. The Company also expects to enter
into operating leases for additional miscellaneous equipment related to its
Triplestack Box Carriers(TM), including reacher-stacker lift trucks used in
cargo operations.
 
     Management believes that available borrowings under the line of credit,
equipment financings, cash flow generated from operations and the net proceeds
of this offering will allow the Company to meet its working capital
requirements, anticipated capital expenditures and other obligations at least
through calendar 1998.
 
INFLATION
 
     Inflation has had a minimal effect upon the Company's profitability in
recent years. Most of the Company's operating expenses are inflation-sensitive,
with inflation generally producing increased costs of operation. The Company
expects that inflation will affect its costs no more than it affects those of
other truckload and marine carriers.
 
                                       25
<PAGE>   27
 
SEASONALITY
 
     The Company's present marine operations are affected by the seasonality of
the Puerto Rico freight market where shipments are generally reduced during the
first calendar quarter and increased during the fourth calendar quarter of each
year in anticipation of Christmas. This seasonality is expected to have a
greater impact on the Company when it increases its capacity with the addition
of two new Triplestack Box Carriers(TM). The Company's over-the-road truckload
operation also experiences some seasonal fluctuations in freight volume, as
shipments have historically decreased during the first calendar quarter. In
addition, the Company's operating expenses historically have been higher in the
winter months due to decreased fuel efficiency and increased maintenance costs
in colder weather. Moreover, the Company's quarterly operating revenue and net
income may continue to fluctuate due to the timing of changes in capacity and
other factors. Accordingly, results of operations are subject to fluctuation,
and results in any period should not be considered indicative of the results to
be expected for any future period.
 
   
     The following table sets forth certain unaudited financial information for
the Company for each of the last nine quarters (in thousands except per share
amounts):
    
 
   
<TABLE>
<CAPTION>
                                                 1995                                    1996                     1997
                                 -------------------------------------   -------------------------------------   -------
                                  FIRST    SECOND     THIRD    FOURTH     FIRST    SECOND     THIRD    FOURTH     FIRST
                                 QUARTER   QUARTER   QUARTER   QUARTER   QUARTER   QUARTER   QUARTER   QUARTER   QUARTER
                                 -------   -------   -------   -------   -------   -------   -------   -------   -------
<S>                              <C>       <C>       <C>       <C>       <C>       <C>       <C>       <C>       <C>
Operating revenues.............  $15,257   $15,832   $15,430   $16,012   $14,568   $14,274   $16,288   $18,018   $16,446
Operating income (loss)........    2,097     2,537     1,790     2,354       966      (187)    1,331     2,315     1,748
Pro forma net income
  (loss)(1)....................    1,039     1,254       841     1,226       443      (199)      636     1,193       909
</TABLE>
    
 
- ---------------
 
   
(1) See Note 3 to the Financial Statements.
    
 
                                       26
<PAGE>   28
 
                               INDUSTRY OVERVIEW
 
   
     Trailer Bridge currently operates in the full-load dry van segment of the
continental U.S. to Puerto Rico freight market and to a lesser degree in the
truckload segment of the domestic trucking industry. The Company also intends to
initiate integrated truckload and marine service between interior points along
the east coast of the continental U.S. which will compete primarily with
truckload and rail intermodal service in north-south traffic lanes. Management
is investigating a number of other potential markets in which the Company could
replicate its unique integrated service model.
    
 
   
     The ocean freight market between the continental U.S. and Puerto Rico is
approximately an $800 million market and is currently estimated to consist of
approximately 310,000 loads per year. The market is unbalanced with more than
three times as much cargo moving to Puerto Rico from the continental U.S. as is
moving in the opposite direction. North-south freight flow imbalances result in
equipment imbalances at interior U.S. points and significantly lower rates for
inbound U.S. cargo compared to outbound U.S. cargo. Puerto Rico shippers select
carriers based primarily upon price. To a lesser extent, criteria such as
frequency, transit time, consistency, billing accuracy and claims experience are
considered.
    
 
   
     Freight moving between the continental U.S. and Puerto Rico is primarily
carried via truck over the inland segment of the freight shipment and via ship
or barge over the marine segment. Most traditional ocean carriers in the Puerto
Rico trade use standard containerized freight systems, employing 20' and 40'
marine containers which for over-the-water shipment are carried on container
ships and for over-the-road shipment are placed on chassis and pulled by
conventional tractors. Ocean carriers generally provide motor carriage of
containers through independent contractors, hired on an as-needed basis.
    
 
   
     As customers realized the cost benefits of consolidating more freight in a
single movement and federal and state governments eased restrictions on
equipment sizes, the prevailing standard trailer size in the domestic inland
truckload industry progressively increased to today's high capacity 53' long,
102" wide dry van trailer. By contrast, the capacity of freight containers used
by shipping companies has not progressively increased over the past 25 years due
to, among other reasons, the significant capital expenditures required to
reconfigure existing ships. Despite the trend of motor carriers toward more
efficient high-cube trailers, the ocean liner trade has retained the use of 20'
and 40' marine containers as the standard unit of containerized marine freight
capacity. Today, no major truckload motor carrier in the U.S. operates 40'
trailers.
    
 
   
     The Company plans to be the first carrier to provide integrated truckload
and marine service between U.S. domestic coastwise points along the eastern
seaboard such as New York and Florida, utilizing high-cube 53' equipment. Based
on studies by Reebie Associates, an independent consultant, the Company believes
that the eastern domestic long-haul, north-to-south full load market is
approximately $3.8 billion per year. The Company will target its planned
coastwise service primarily at long-haul, price-sensitive domestic freight which
is currently moving on rail intermodal. The railroad movement of trailers and
containers on flatcars has rapidly grown into a $5.8 billion industry in recent
years, primarily due to the per mile linehaul cost advantage of rail intermodal
over comparable truckload rates on longer hauls. The Company's planned
integrated coastwise truckload and marine freight service is designed to take
further advantage of shippers' proven willingness to move from one mode of
transport to another to reduce distribution costs. Accordingly, the Company will
primarily compete with truckload and rail intermodal service on the basis of
price.
    
 
                                       27
<PAGE>   29
 
                                    BUSINESS
 
OVERVIEW
 
   
     Trailer Bridge, headquartered in Jacksonville, Florida, is an integrated
trucking and marine freight carrier that provides truckload freight
transportation primarily between the continental U.S. and Puerto Rico. Founded
in 1991 by transportation pioneer Malcom P. McLean, the Company combines an
efficient and dedicated motor carrier with a low cost barge and tug marine
transportation system. Trailer Bridge is the only company serving markets
governed by the Jones Act which exclusively operates marine vessels fully
configured to carry 48' and 53' long, 102" wide, "high-cube" trailers. This
configuration enables the Company to achieve equipment utilization rates and
other operating efficiencies not readily available to traditional ocean carriers
that primarily use smaller capacity equipment, such as 40' containers. The
Company believes that as a result of these and other efficiencies, its total
unit costs per mile are the lowest of any carrier operating between the
continental U.S. and Puerto Rico.
    
 
   
     Trailer Bridge intends to achieve significant growth by providing the
lowest cost freight transportation service to markets well suited to its
high-cube integrated truckload and marine freight system. Based on volume and
pricing data, the Company believes that there are a number of markets in which
the Company's unique transportation system can provide superior full-load
service at a significant cost advantage over existing modes of truckload and
rail intermodal transportation.
    
 
   
     Trailer Bridge's differentiated service quickly gained the acceptance of
U.S. to Puerto Rico shippers, leading to rapid growth and high equipment
utilization. In 1993, the Company's first full year of operation, Trailer Bridge
achieved a 93% outbound (continental U.S. to Puerto Rico) vessel utilization
rate and captured 5% of the continental U.S. to Puerto Rico marine freight
market. In response to the rapid market share gains experienced by Trailer
Bridge, in 1996 the Company increased its vessel capacity by 56% by inserting
midsections ("mid-bodies") into its two existing barges, increasing the capacity
of each barge from 266 to 416 48' equivalent truckload units. These
roll-on/roll-off barges are chartered from an affiliate.
    
 
   
     Trailer Bridge will increase its vessel capacity by an additional 56% in
late 1997 and early 1998 when it takes delivery of two 408' long container
carrying barges designed specifically for the Company's integrated truckload
marine transportation system and bearing the Company's Triplestack Box
Carrier(TM) trade name. The Triplestack Box Carriers(TM) will be versatile,
low-draft vessels that have a capacity of 213 53' containers, stacked three-high
on a single deck. Construction of these two vessels began in March 1997. Upon
completion, the vessels will be deployed in the Company's existing Puerto Rico
freight operation. Trailer Bridge also intends to contract for the construction
of three additional Triplestack Box Carriers(TM) which it intends to deploy in
coastwise service between New York and Florida. The Company plans to investigate
other marine markets which are well suited for its unique, cost-efficient
transportation service, such as from the continental U.S. to Hawaii or Alaska.
    
 
   
COMPETITIVE STRENGTHS
    
 
     Management believes that the Company's principal competitive strengths are:
 
   
     - Significant Operating Cost Advantage.  Trailer Bridge believes that it is
      the lowest cost provider of freight transportation between the continental
      U.S. and Puerto Rico. Lower overall operating costs are achieved through
      significantly higher equipment utilization and lower marine linehaul costs
      than those of traditional ocean carriers. The Company's inland trucking
      operation achieves higher equipment utilization and lower unit trucking
      costs by using 48' and 53' high-cube trailers. This system provides
      customers with over 50% more interior capacity than 40' marine containers
      but with similar inland trucking costs. The Company's marine system uses
      towed ocean-going barges instead of self propelled container ships to
      deliver equivalent units of capacity at significantly lower capital and
      operating costs. Barges are less complex and equipment intensive and
      therefore can be acquired or built at lower costs per unit of capacity
      than container ships. Furthermore, towed barge systems can be
    
 
                                       28
<PAGE>   30
 
      operated with lower per unit personnel and fuel costs due to the less
      restrictive Coast Guard manning requirements and lower maximum speed of
      ocean going tugs. Other components of the Company's low-cost operating
      structure include Trailer Bridge's use of uniform, modern fleet equipment
      to maximize utilization and flexibility and minimize operating costs, as
      well as an emphasis on hiring and retaining qualified and reliable drivers
      to reduce the costs of insurance, recruiting, fuel and maintenance.
 
   
     - Domestic Truckload Operations.  The Company believes that it is the only
      carrier using its own fleet of tractors and high-cube dry van trailers to
      provide transportation services between interior points in the continental
      U.S. and Puerto Rico. By using high-cube equipment, the mainstay of the
      domestic truckload industry, and a centralized dispatch system, the
      Company can more effectively compete for and obtain domestic non-Puerto
      Rico truckload freight while repositioning equipment for Puerto Rico
      shipments. As a result, the Company believes that it operates with lower
      empty miles and higher equipment utilization than its competitors in the
      Puerto Rico trade. The Company believes that it is able to provide more
      reliable and consistent service with a company-operated truckload fleet
      than traditional ocean carriers generally provide using a variety of
      smaller independent contractors.
    
 
     - Centralized Operation in Strategic Location.  Trailer Bridge operates a
      centralized truckload operation from its headquarters in Jacksonville.
      Because approximately 70% of the Company's truckload freight is dispatched
      through Jacksonville on a regular schedule to meet weekly barge sailings
      to Puerto Rico, the Company is able to purchase a large portion of its
      fuel locally at favorable bulk rates and can schedule and perform routine
      maintenance at the Company's terminal facilities at lower cost and with
      minimal interruption to tractor dispatch efficiency. Regular truck routing
      through Jacksonville also enables the Company to offer its drivers a more
      routine schedule with more frequent stops at home, leading to higher
      driver retention. Additionally, the Company's centralized Jacksonville
      headquarters is also strategically located near key southern rail and
      highway endpoints, connecting cities in the continental U.S. to Puerto
      Rico and other Caribbean points.
 
   
     - Emphasis on U.S. Domestic Ocean Trade.  The Company concentrates its
      marine operations in markets governed by the Jones Act. The Jones Act
      prevents foreign-built or foreign-crewed vessels from competing in ocean
      trade between ports in the U.S., including the non-contiguous areas of
      Puerto Rico, Alaska, Hawaii and Guam. Although the Company believes that
      its costs are competitive with those of foreign flagged carriers, it has
      initially focused on Jones Act protected markets to take advantage of the
      larger differential between its costs and the costs of other Jones Act
      protected U.S. flag carriers. Furthermore, two of the largest carriers in
      the Puerto Rico trade have agreed with the U.S. Maritime Administration to
      certain restrictions on adding capacity in the Jones Act trades, including
      their respective Puerto Rico services, as a condition to the receipt of
      certain payments.
    
 
   
     - Experienced Management Team.  The Company's officers and directors have
      extensive experience in the transportation industry, including an average
      of over 15 years in the marine and trucking industries. All but one member
      of the Company's management team have been with the Company since its
      inception. The scope of management experience at Trailer Bridge is
      well-balanced between both trucking and marine transportation. The
      Company's Chief Executive Officer and President have been involved in
      maritime trade for 19 and 26 years, respectively, and the Company's Vice
      President of Sales has over 25 years of experience in the trucking
      industry. The Company believes that the diverse skills of its management
      team have permitted Trailer Bridge to conceive, implement and expand a
      unique integrated transportation system that applies the best practices of
      this country's cost-efficient truckload business to the marine sector.
    
 
                                       29
<PAGE>   31
 
GROWTH STRATEGY
 
     The following are the key elements of the Company's growth strategy:
 
   
     - Increased Market Share of Puerto Rico Market.  Trailer Bridge plans to
      increase the capacity of its Puerto Rico service by adding two Triplestack
      Box Carriers(TM), which will increase the Company's overall capacity by
      56% and allow the Company to increase its frequency of service to Puerto
      Rico to two sailings per week from the current weekly service. Management
      believes that the Company's lack of available capacity and its limited
      service frequency have, to date, limited its volume of business with
      certain existing customers and precluded other customers from utilizing
      the Company's services. The Triplestack Box Carriers(TM) are designed
      specifically to carry high capacity 53' containers, which the Company
      believes are preferred by customers and will therefore increase demand for
      its services. Added vessel capacity and frequency will also allow the
      Company to pursue additional backhaul revenue opportunities and seek high
      equipment utilization because of the more balanced availability of
      trucking capacity.
    
 
   
     - Initiation of Coastwise Service.  Following its planned expansion of
      Puerto Rico service, the Company intends to commence a twice-weekly New
      York to Florida coastwise service utilizing three additional Triplestack
      Box Carriers(TM). These vessels, combined with the Company's trucking
      capabilities and expertise in operating an integrated system, are expected
      to provide lower linehaul costs than typical intermodal truckload and rail
      doublestack train service. This will in turn allow the Company to compete
      effectively with truckload and rail intermodal carriers on the basis of
      price. The Company believes the New York to Florida traffic lane is the
      most attractive market in which to initiate its coastwise service but
      believes there are numerous other coastwise traffic lanes (including Gulf
      coast and West coast lanes) in which the Company can provide a more cost
      efficient freight service for shippers. There can be no assurance that the
      Company will be able to compete effectively with truckload and rail
      intermodal carriers. The Company will not be able to match the delivery
      times offered by many truckload carriers and may not be able to match the
      delivery times of all rail intermodal carriers.
    
 
   
     - Service to Other Jones Act and Offshore Markets.  The freight markets
      between the continental U.S. and points in Hawaii and Alaska are similar
      in overall size to the Puerto Rico market and are served by traditional
      marine carriers that do not utilize 48' or 53' conveyance units. The lack
      of appropriate and available port facilities in Hawaii and Alaska acts as
      a barrier to entry in those markets. However, the design and loading
      requirements of the Company's Triplestack Box Carrier(TM) should allow the
      Company to serve these and other new markets from waterfront sites that do
      not require the traditional infrastructure investments associated with
      port facilities. Additionally, the Company believes there are other
      potential non-Jones Act markets such as the Dominican Republic and Mexico
      where the Triplestack Box Carrier(TM) system could be quickly implemented
      with minimal investment in port facilities. The Company has no current
      plans to expand to any such markets.
    
 
   
     - Capacity and Environmental Constraints on Other Modes.  On a longer-term
      basis, the Company believes that its planned coastwise service will
      benefit from growing capacity constraints in both the rail and highway
      systems. Management also believes that the Company's planned coastwise
      service will be more environmentally attractive than the rail and truck
      transport sectors, as it emits lower fuel emissions and operates at
      greater distances from densely populated areas. Finally, the increasing
      publicity attendant to train and truck accidents, particularly those
      involving passenger automobiles, should offer an attractive political
      environment for expansion of the Company's maritime service.
    
 
                                       30
<PAGE>   32
 
OPERATIONS
 
   
     Trailer Bridge operates a fleet of 154 tractors and 1,937 high-cube
trailers which transport truckload freight between the Company's Jacksonville
port facility and inland points in the U.S. The Company also provides full
truckload service between interior points within the continental U.S., primarily
to increase equipment utilization, minimize empty miles and maximize revenue
while repositioning equipment to carry Puerto Rico bound freight. The Company
maintains a centralized dispatch and customer service operation at its
Jacksonville headquarters to schedule pickup and delivery of customer freight.
The operations center features a fully integrated computerized dispatch and
customer service network. Customer service representatives solicit and accept
freight, quote freight rates and serve as the primary contact with customers.
Dispatch and customer service personnel work together to coordinate Puerto Rico
and non-Puerto Rico freight to achieve the most optimum load balance and
minimize empty miles within the Company's truckload operation.
    
 
   
     Trailer Bridge currently operates two 736' triple-deck, roll-on/roll-off
ocean-going barges chartered from an affiliate. See "Certain Transactions."
Loading of the barges is performed with small maneuverable yard tractors
operated by stevedores hired by an outside contractor. Once per week, the
Company's two barge vessels sail between San Juan and Jacksonville, one in each
direction. One vessel is scheduled to arrive in Jacksonville on Tuesday at 8:00
a.m. and depart on Thursday at 2:00 p.m., while the other vessel is scheduled to
arrive in San Juan on Wednesday at 6:00 a.m. and depart on Wednesday at 8:00
p.m. Each barge is towed at approximately 9 knots by one 8,000 horsepower
diesel-powered tug. The tugs are time-chartered and are manned by employees of
the unaffiliated tug owner. Compared to a self-propelled vessel, a towed barge
has reduced Coast Guard manning requirements and higher fuel efficiency.
Similarly, the large number of U.S. tugs available for charter provides the
Company with a reliable source for towing services.
    
 
MARKETING AND CUSTOMERS
 
   
     The Company's sales and marketing function is led by senior management and
sales professionals based in Jacksonville, San Juan and other key strategic U.S.
cities. These sales personnel aggressively market Trailer Bridge to shippers as
a customer-oriented provider of value-priced and dependable service. The Company
targets major shippers with high volume, repetitive shipments whose freight
lends itself to integrated trucking and marine service.
    
 
     The Company believes that price is the primary determinant in the freight
lanes in which it is involved. Nonetheless, the Company also believes that
Trailer Bridge has a competitive advantage through its ability to provide better
service that results from its single company control of the entire freight
movement over land and water. This service frees the customer from the
operational complexities of coordinating the interface between over-the-road and
marine service. The Company's customer service philosophy has generated
increasing demand from existing customers for additional equipment and sailings
and has led to ongoing relationships with customers such as Chrysler, General
Motors, K Mart, General Electric and DuPont.
 
   
     The Company has a diversified customer base. Typical shipments to Puerto
Rico include furniture, consumer goods, toys, new and used cars and apparel.
Typical shipments from Puerto Rico include health products, electronics, shoes
and scrap aluminum. Management intends to continue the Company's efforts both to
increase business with existing customers and add new core carrier
relationships. The Company's top 5, 10, and 25 customers accounted for 15.8%,
22.9% and 35.2% of revenue, respectively, in 1996.
    
 
   
     The Company has written contracts with the majority of its customers. These
contracts generally specify service standards and rates, eliminating the need
for negotiating the rate for individual shipments. Although a contract typically
runs for a specified term of at least one year, it generally may be terminated
by either party upon 30 days' notice. The penalties for a shipper for breach of
contract are minimal.
    
 
                                       31
<PAGE>   33
 
EXISTING AND PLANNED VESSELS
 
   
     The Company's present vessels are 736' by 104' triple-deck roll-on/roll-off
barges chartered from an affiliate. Each deck has ten lanes which are accessed
from the stern of the vessel via ramp structures in Jacksonville and San Juan
that have been built specifically for the Company. Four lanes on each vessel
have been converted to carry new and used automobiles on car decks that allow
approximately 11 cars to fit in the space previously used for one 48' trailer.
The trailers are secured on the vessel by attachment to pullman stands which are
engaged and disengaged with specially configured yard tractors used to pull the
trailers into position on the vessel. The present vessels can be fully
discharged and re-loaded within one eight hour shift, although the Company
generally makes use of additional available slack time in Jacksonville to
schedule cargo activity over periods that will minimize total cost.
    
 
   
     The two Triplestack Box Carriers(TM) to be used in the Puerto Rico traffic
lane are single deck barges. These 408' by 100' vessels are being built at
Halter Marine Group, Inc.'s Pearlington, Mississippi shipyard under fixed-priced
contracts which call for delivery of the first vessel in November 1997 and the
second vessel in January 1998. In the Puerto Rico service, the two Triplestack
Box Carriers(TM) are expected to achieve the scheduled service speed of 9 knots
with a 6,500 horsepower tug and attain tow speeds of approximately 11 knots with
larger tugs. These vessels will utilize the same port facilities as the existing
barge vessels. See "Business -- Port Facilities." Wheeled vehicles known as
reacher-stackers will carry and load the containers. These highly maneuverable
vehicles are currently used by railroads to load containers on rail cars for
intermodal transportation. The reacher-stackers are significantly less expensive
than the cranes typically required for loading and unloading containers from the
holds of large cargo ships and will instead directly access the deck of the
vessel via simple and movable linear ramps. The Company believes that the total
cargo handling cost per unit of the Triplestack Box Carriers(TM) in the Puerto
Rico traffic lane will be similar to that experienced with its present
roll-on/roll-off vessels. The Company intends to acquire three additional
Triplestack Box Carriers(TM) in 1998 to use in the coastwise traffic lanes as a
cost-efficient alternative to truckload and rail intermodal. See "Management's
Discussion and Analysis of Financial Condition and Results of
Operations -- Liquidity and Capital Resources" and "Business -- Growth
Strategy."
    
 
REVENUE EQUIPMENT
 
   
     Trailer Bridge's equipment strategy is to operate modern tractors and
trailers in order to (i) reduce fuel, maintenance and parts costs, (ii) increase
reliability, and (iii) help attract and retain drivers. At March 31, 1997, the
Company had 154 tractors. The Company's practice is to trade or replace its
tractors on a 450,000-mile cycle which generally occurs during the fourth year.
    
 
   
     Trailer Bridge has scheduled deliveries of approximately 75 new tractors
during the remainder of 1997 and 25 new tractors during 1998. After the planned
trade-in or sale during 1997 of all its model year 1993 tractors, the Company
will have a fleet of approximately 145 owned tractors with an average age of
nine months. Management anticipates that the Company's ongoing fleet upgrade
program will significantly decrease its maintenance, repair and parts expenses.
In addition, the Company has a fuel consumption incentive program for the
drivers, which is expected to improve the fuel consumption of its new fleet. All
of the new power units are conventional tractors (engine-forward) that are
preferred by drivers. These units include, among other amenities, a large
"condo" sleeper compartment with full standing room.
    
 
   
     At March 31, 1997, the Company operated 1,937 dry van trailers, 1,772 of
which were 48' x 102" models and 165 of which were 53' x 102" models. The
Company's current practice is to trade or replace owned trailers on a seven-year
cycle and replace leased trailers with owned trailers as leases expire. Since
the trailers spend a significant amount of time on the Company's vessels and in
Puerto Rico, the Company's trailers incur less mileage per year than those used
by a typical truckload carrier. For instance, in 1996 the Company averaged
approximately 10,500 highway miles per trailer
    
 
                                       32
<PAGE>   34
 
compared to approximately 50,000 miles per year averaged by typical domestic
truckload carriers. For this reason, the Company believes that its trailers have
a longer effective life despite the corrosive ocean environment encountered on
the vessels.
 
   
     The Company has scheduled deliveries of approximately 850 new containers
during late 1997 and early 1998, all of which are 53' models that will be
utilized by the two new Triplestack Box Carriers(TM) to be deployed in the
Puerto Rico traffic lane. These containers are being built to the Company's
specifications and are similar to the 53' containers utilized on the most
efficient rail doublestack operation. The Company has also contracted to
purchase 550 new chassis units which will be utilized in combination with the
53' containers for over-the-road carriage. Under its fixed-price contract with a
large container manufacturer, Trailer Bridge has an option to increase its order
by up to 250 additional 53' container and chassis units.
    
 
   
     The Company performs preventative maintenance on equipment at its
Jacksonville operations center, with major maintenance and repairs handled by
outside contractors.
    
 
DRIVER RECRUITING AND RETENTION
 
   
     Trailer Bridge places great emphasis on driver satisfaction and has made
significant investments to improve its drivers' employment experience. The
Company offers competitive compensation and full health care benefits
differentiating it from many truckload operators. Management also promotes
driver retention by assigning drivers to a single dispatcher, regardless of
geographic area, awarding dedicated routes and offering more predictable home
time resulting from a central hub of operations. The Company believes its driver
turnover is well below that typically reported by other truckload carriers
despite an industry-wide driver shortage and vigorous competition for drivers
during the past several years.
    
 
   
     In recent periods the Company has significantly reduced the number of
owner-operators in connection with its decision to decrease domestic truckload
business not related to Puerto Rico movements. At March 31, 1997, the Company
had only 13 owner-operators. Nevertheless, the Company intends to utilize the
flexibility of adding and removing owner-operators from its driver work force to
address driver and equipment needs in the future. The Company compensates owner-
operators as employees, affording them the same benefits as regular Company
drivers. Owner-operators receive a flat rate per mile to cover equipment costs,
fuel and maintenance.
    
 
FUEL AVAILABILITY AND COST
 
   
     The Company actively manages its fuel costs by requiring drivers to fuel in
Jacksonville at an offsite fuel facility where the Company has established a
bulk purchasing arrangement. Whenever possible enroute, drivers are required to
fuel at truck stops and service centers with which the Company has established
volume purchasing arrangements. The Company offers fuel-conservation bonuses to
its drivers based on achieving miles per gallon goals.
    
 
   
     Although the Company pays for the marine fuel used by the large tugs it
charters, the actual fuel loading is controlled by tug crew personnel employed
by the tug owner. The fuel is purchased and loaded in Jacksonville at a nearby
fuel facility during cargo loading operations. By negotiating directly with fuel
vendors and offering volume contracts for its marine fuel needs, the Company has
obtained better prices than it would have otherwise been able to attain.
    
 
   
     Trailer Bridge does not engage in any fuel hedging activities. The Company
historically has been able to pass through most increases in fuel prices to
customers in the form of higher rates, although there can be no assurance that
this will continue in the future. See "Risk Factors -- Fuel Price Fluctuations."
    
 
                                       33
<PAGE>   35
 
SAFETY AND INSURANCE
 
   
     Trailer Bridge emphasizes safety in all aspects of its operations. The
Company maintains its own strict standards for recruiting drivers, including a
minimum of five years of verifiable commercial driving experience, a safe
driving history and a successful physical examination, including drug and
alcohol testing. Its ongoing driver safety program includes an initial
orientation for all new drivers, 100% log monitoring and strong adherence to all
speed and weight regulations.
    
 
   
     The Company bids annually for both marine and land insurance policies.
Major coverages include hull and protection indemnity, pollution, excess
liability, marine cargo, truckers liability, workers' compensation and
commercial property. Management believes existing coverages are adequate to
cover reasonably anticipated claims. However, there can be no assurance that
premium levels will not increase or that coverage will be adequate in the
future. See "Risk Factors -- Claims Exposure and Insurance Costs."
    
 
TECHNOLOGY
 
     The Company utilizes an IBM AS-400 computer system to handle its accounting
and operations requirements. The computer system links Company headquarters, the
truck operations center, the San Juan office and the marine terminals in
Jacksonville and San Juan. The system enhances the Company's operating
efficiency by providing cost effective access to detailed information concerning
available equipment, loads, shipment status and specific customer requirements,
and permits the Company to respond promptly and accurately to customer requests.
 
   
     The Company's electronic data interchange ("EDI") capability allows
customers to tender loads, receive load confirmation, check load status and
receive billing information via computer. The Company's EDI system also is
designed to accelerate receivables collection. The Company's largest customers
require EDI service from their core carriers. Management believes that advanced
technology will be required by an increasing number of large shippers as they
reduce the number of carriers they use in favor of core carriers.
    
 
     The Company believes that the open structure of the internet will replace
many of the traditional EDI functions and intends to expand its website
(www.trailerbridge.com) to accommodate such technology.
 
PROPERTIES
 
   
     Trailer Bridge is headquartered in Jacksonville, Florida, where it is
completing construction of a 16,000 square foot office building adjacent to its
owned truck operations center. Upon completion in mid-1997, this facility will
centralize 75 Jacksonville personnel in one location. The new office building
has also been designed so that additions can be constructed to serve the
Company's future needs. The truck operations center property was purchased in
1996 and consists of 17.8 acres near Interstate 95, approximately 2 miles from
the Company's marine terminal on Blount Island. In addition to the new office
building, the property includes a 11,400 square foot tractor maintenance shop
where oil changes and light preventative maintenance are performed, a trailer
washing facility, a drivers lounge and parking space for tractors and trailers.
The Company believes that additional acreage contiguous to its truck operations
center will be available to accommodate future expansion.
    
 
     The Company maintains small sales office facilities in Georgia, North
Carolina, Illinois, Ohio and New Jersey which are utilized by sales personnel.
The Company also rents a 2,600 square foot office in San Juan where 11 Puerto
Rico administrative and sales personnel are based.
 
PORT FACILITIES
 
     The Company utilizes port facilities in Jacksonville and San Juan where its
vessels are loaded and freight is stored awaiting further movement by either
vessel or truck. Trailer Bridge's terminal in Jacksonville is located on Blount
Island and consists of a berthing area and 17 acres leased from the
 
                                       34
<PAGE>   36
 
Jacksonville Port Authority. The lease, which expires in 2002, allows the
Company to use the berthing area on a preferential, although non-exclusive,
basis and the land area on an exclusive basis. The Company pays the Jacksonville
Port Authority a monthly rental payment plus a wharfage payment based upon total
cargo volume. The Company's marine terminal in San Juan consists of a berthing
area and 31 acres that the Company utilizes on a preferential basis under a
stevedoring services agreement with the contractor who provides cargo handing
services. This agreement, which expires in 2006, calls for the Company to make
fixed payments as well as payments based upon total cargo volume and the
prevailing wharfage rates of the Puerto Rico Ports Authority.
 
   
     Both of the present port facilities have been improved with triple-deck
floating ramp structures. These ramp facilities were built by the present vessel
owner and are included in the charter payments Trailer Bridge makes to such
affiliated owner. The new Triplestack Box Carriers(TM) will not need to utilize
the existing ramps but will instead be accessed from simple, movable ramps which
will be substantially smaller than the existing ramps used by the Company.
Trailer Bridge believes that its present marine terminals in Jacksonville and
Puerto Rico are sufficient to accommodate the expected growth from the
introduction of the two new vessels.
    
 
   
     The Company's expansion into coastwise traffic lanes will require new port
facilities. Due to their shallow draft, relatively small overall size and
ability to load without significant shore-side ramp facilities or cranes,
Triplestack Box Carriers(TM) can be utilized at port facilities that would not
be appropriate for the Company's present vessels or for other similar-sized
vessels. These facilities include private sites that have not previously been
utilized for cargo operations. Trailer Bridge believes that it will be able to
find sufficient marine sites that lend themselves to the low-cost unloading and
loading operation it envisions for the Triplestack Box Carriers(TM) to be
deployed in the coastwise traffic lanes. The Company has identified several
suitable sites but has not reached any agreements or understandings regarding
their use.
    
 
COMPETITION
 
   
     The Company currently competes with four carriers for freight moving
between the U.S. and Puerto Rico. The current operators in the Puerto Rico trade
are Navieras de Puerto Rico ("NPR"), Sea-Land Service, Inc., Crowley American
Transport, Sea-Barge Marine and Trailer Bridge. Based on available industry data
for the first quarter of 1997, NPR, which was purchased from the Puerto Rico
government in a leveraged buyout in 1995, has approximately 32% of the market
and operates five container vessels configured to carry primarily 40' marine
containers. Sea-Land Service, Inc., a subsidiary of CSX Corporation, has
approximately 24% of the market and operates five container vessels that also
carry mainly 40' containers. Crowley American Transport, a subsidiary of
privately held Crowley Maritime Corp., has approximately 30% of the market and
operates nine roll-on/roll-off barges in various services between the U.S. and
Puerto Rico. Although Crowley now uses some 48' trailers, its main equipment
size is 45' by 96" wide trailers. Sea Barge Marine has approximately 7% of the
market with four container barges that primarily carry 40' marine containers.
    
 
   
     Puerto Rico shippers select carriers based primarily upon price. To a
lesser extent, criteria such as frequency, transit time, consistency, billing
accuracy and claims experience are considered. The Company faces vigorous price
competition from competitors in the Puerto Rico market, two of which are part of
larger transportation organizations that possess greater financial resources
than the Company. While the Company believes it is the lowest cost per unit
operator in the Puerto Rico traffic lane, it does not always offer the lowest
effective price as certain operators at times engage in a practice of freight
rate discounting.
    
 
   
     The Company's planned coastwise service is expected to compete primarily
with large railroads that move intermodal freight and, to a lesser extent,
trucking companies. Intermodal freight service competes primarily on the basis
of price. Although trucking companies serving the same routes as the Company's
contemplated coastwise service typically target a customer base that requires
faster delivery times, such trucking companies also compete primarily on the
basis of price. Many of the
    
 
                                       35
<PAGE>   37
 
   
Company's potential competitors are significantly larger and possess
substantially greater financial resources than the Company. The Company intends
to compete by offering customers value-based pricing derived from its lower
linehaul cost per unit. The Company will target customers with less time
sensitive-freight whose priority is reducing freight costs rather than obtaining
the shortest possible transit times.
    
 
   
     The truckload segment of the trucking industry is highly competitive and
fragmented, and no carrier or group of carriers dominates the market. The
Company's non-Puerto Rico domestic truckload operations, which are used
primarily to balance its core Puerto Rico service, compete with a number of
trucking companies as well as private truck fleets used by shippers to transport
their own products. Truckload carriers compete primarily on the basis of price.
The Company's truck freight service also competes to a limited extent with rail
and rail-truck intermodal service, but the Company attempts to limit this
competition by seeking more time and service-sensitive freight. There are other
trucking companies, including diversified carriers with larger fleets,
possessing substantially greater financial resources and operating more
equipment than the Company.
    
 
REGULATION
 
     As a common and contract motor carrier, the Company is regulated by the
Surface Transportation Board (the successor federal agency to the Interstate
Commerce Commission) and various state agencies. The Company's drivers,
including owner-operators, also must comply with the safety and fitness
regulations promulgated by the Department of Transportation, including those
relating to drug testing and hours of service. For routes in Canadian provinces,
the Company must comply with certain customs and border crossing requirements
and other Canadian regulations, none of which have a material effect on the
Company.
 
   
     The Company's operations are subject to various federal, state and local
environmental laws and regulations, implemented principally by the Environmental
Protection Agency and similar state regulatory agencies. These regulations
govern the management of hazardous wastes, discharge of pollutants into the air,
surface and underground waters, and the disposal of certain substances.
Management is not aware of any water or land fuel spills or hazardous substance
contamination on its properties and believes that its operations are in material
compliance with current environmental laws and regulations.
    
 
   
     The Company's marine operations are conducted in the U.S. domestic trade. A
set of federal laws known as the Jones Act requires that only U.S. built, owned
and crewed vessels move freight between ports in the U.S., including the
noncontiguous areas of Puerto Rico, Alaska, Hawaii and Guam. These marine
operations are subject to regulation by various federal agencies, including the
Surface Transportation Board, the U.S. Maritime Administration and the U.S.
Coast Guard. These regulatory authorities have broad powers governing activities
such as operational safety, tariff filings of freight rates, certain mergers,
contraband, environmental contamination and financial reporting. Management
believes that its operations are in material compliance with current marine laws
and regulations, but there can be no assurance that current regulatory
requirements will not change. See "Risk Factors -- Potential Loss of Jones Act
Protection."
    
 
EMPLOYEES
 
   
     At March 31, 1997, Trailer Bridge had 244 employees, 140 of whom were
drivers. Management believes that its computerized operation and efficient work
force will permit significant fleet expansion without a corresponding increase
in the number of non-driver employees. Management believes it has a good
relationship with the Company's employees.
    
 
                                       36
<PAGE>   38
 
LEGAL PROCEEDINGS
 
   
     The Company from time to time is a party to litigation arising in the
ordinary course of its business, substantially all of which involves claims for
personal injury and property damage incurred in the transportation of freight.
The Company presently is not a party to any legal proceeding other than
litigation arising from vehicle accidents or cargo damage, and management is not
aware of any claims or threatened claims that reasonably would be expected to
exceed insurance limits or have a material adverse effect upon the Company's
operations or financial position.
    
 
                                       37
<PAGE>   39
 
                                   MANAGEMENT
 
EXECUTIVE OFFICERS AND DIRECTORS
 
   
     The table below sets forth information concerning the Company's executive
officers and directors:
    
 
   
<TABLE>
<CAPTION>
                      NAME                        AGE                    POSITION(1)
                      ----                        ---                    -----------
<S>                                               <C>   <C>
Malcom P. McLean................................  83    Director
John D. McCown(2)...............................  42    Chairman of the Board and Chief Executive
                                                          Officer
Ralph W. Heim...................................  51    President and Chief Operating Officer
Wayne Hodges....................................  47    Vice President of Sales
J. Edward Morley................................  49    Vice President of Operations
Mark A. Tanner..................................  45    Vice President of Administration and Chief
                                                          Financial Officer
Robert van Dijk.................................  51    Vice President of Pricing
William G. Gotimer, Jr..........................  38    Secretary and General Counsel
</TABLE>
    
 
- ---------------
 
(1) Directors are elected annually. Executive officers serve at the pleasure of
    the Board of Directors.
(2) Will become a member of the Audit Committee upon the closing of the
    offering.
 
   
     Mr. McLean, a director since April 1991, is the founder and principal
stockholder of Trailer Bridge. His principal business activity during the past
five years has related to developing Trailer Bridge. He served as President from
June 1991 to July 1992 and from January 1995 to November 1995. Mr. McLean is a
pioneer in transportation who is responsible for a number of innovations in both
trucking and shipping and who is best known as the founder of container
shipping. He built McLean Trucking Company into one of the largest and most
profitable trucking companies in the U.S., where it was the first major user of
diesel engines in its tractors. In the mid-1950's, he purchased two steamship
companies which were combined to form Sea-Land Service, Inc. ("Sea-Land") which
introduced and developed container shipping. Following the sale of Sea-Land in
1968, Mr. McLean went on to found McLean Industries whose principal subsidiary,
U.S. Lines, became the largest container shipping company in the world. His
business accomplishments led to his induction in the Fortune Magazine Business
Hall of Fame, and he was referred to by a leading business magazine as "one of
the few men who changed the world."
    
 
   
     Mr. McCown, a director since April 1991, has served as the Chairman of the
Board and non-employee Chief Executive Officer since November 1995. From July
1992 to November 1995, Mr. McCown was Vice President of the Company. In addition
to his role at Trailer Bridge, he is President and Chief Executive Officer of
Kadampanattu Corp., an affiliate of Trailer Bridge that owns the two vessels now
utilized by Trailer Bridge in its present Puerto Rico service. Mr. McCown has
worked for Malcom P. McLean in various capacities since 1980. Mr. McCown is a
graduate of Harvard Business School (MBA, 1980) and Louisiana State University
(BBA, 1975). Prior to joining McLean Industries in 1980, Mr. McCown worked at
U.S. Lines, a subsidiary of McLean Industries, and at National Bank of North
America as a corporate loan officer. Commencing with this offering, Mr. McCown
will become an employee of the Company and is expected to devote substantially
all of his working time to the Company. See "Risk Factors -- Dependence on Key
Personnel" and "Certain Transactions."
    
 
   
     Mr. Heim has served as President since November 1995 and Chief Operating
Officer since January 1992. From May 1991 until November 1995, Mr. Heim served
as Vice President of the Company. Prior to joining Trailer Bridge in 1991, Mr.
Heim worked at Crowley Maritime Corporation for five years in various operating
capacities primarily related to its Puerto Rico service. His other
transportation experience includes more than 15 years with Sea-Land, Puerto Rico
Marine Manage-
    
 
                                       38
<PAGE>   40
 
ment and U.S. Lines in diverse domestic and international assignments. Mr. Heim
graduated from Jacksonville University with a B.S. in Business Management.
 
   
     Mr. Hodges has served as Vice President of Sales since November 1995. Prior
to joining Trailer Bridge in September 1995, he served as General Sales Manager
for M.S. Carriers, a major nationwide truckload carrier based in Memphis. Mr.
Hodges was that company's first salesman, beginning in 1982. Prior to his
association with M.S. Carriers, Mr. Hodges' trucking experience included
terminal manager positions at Mistletoe Express and United Parcel Service as
well as a branch manager position at a trailer sales dealer.
    
 
   
     Mr. Morley has served as Vice President of Operations since July 1992 and
is responsible for marine and terminal operations. Prior to joining Trailer
Bridge in 1991, Mr. Morley was with Sea-Land where he was responsible for
operations in Puerto Rico from 1990 to 1991. Mr. Morley's overall transportation
experience with major container transportation companies spans over 25 years.
    
 
   
     Mr. Tanner, a CPA, has served as Vice President of Administration and Chief
Financial Officer since January 1992. Mr. Tanner joined Trailer Bridge in 1991
from Crowley Maritime where he was Manager of Analysis and Statistics for four
years. His prior experience includes three years as Manager of Corporate
Planning for The Charter Company, which was a Jacksonville based $5 billion
publicly-held company, and five years in public accounting.
    
 
   
     Mr. van Dijk has served as Vice President of Pricing since July 1992 and
directs all pricing related activities. Prior to joining Trailer Bridge in 1991,
Mr. van Dijk worked for Crowley Maritime, where he directed pricing for the
Puerto Rico service. Mr. van Dijk's pricing related experience includes over 30
years with American Transport, U.S. Lines, Weyerhauser Shipping, Sea-Land and
Holland America Lines.
    
 
   
     Mr. Gotimer has served as non-employee General Counsel since 1991. Mr.
Gotimer also acts as legal counsel for Malcom P. McLean, including General
Counsel for Kadampanattu Corp. His previous experience includes legal counsel
with British Airways, Plc., Pan American World Airways and McLean Industries.
Mr. Gotimer has an LL.M. degree in Taxation from New York University School of
Law and both a JD and BS degree in accounting from St. John's University.
Commencing with this offering, Mr. Gotimer will become a part-time employee of
the Company. See "Certain Transactions."
    
 
   
     Following completion of the offering, the Company intends to add two
independent directors to its Board. The Company has not yet chosen such
directors.
    
 
COMMITTEES
 
   
     Following completion of the offering, the Board of Directors intends to
establish an Audit Committee comprised initially of John D. McCown and the
Company's two independent directors and a Compensation Committee comprised of
the Company's two independent directors. The Audit Committee will have
responsibility for reviewing audit plans and discussing audit work, internal
controls and related matters with the Company's independent public accountants,
reviewing the audit report and any accompanying recommendations, and nominating
independent public accountants to perform the annual audit. The Compensation
Committee will have responsibility for reviewing the compensation of the
Company's executive officers, making recommendations to the Board of Directors
and administering the Company's Incentive Stock Plan. See "Management --
Incentive Stock Plan."
    
 
                                       39
<PAGE>   41
 
EXECUTIVE COMPENSATION
 
     The following table summarizes the compensation paid or accrued by the
Company, for services rendered during 1996, to the Company's Chief Executive
Officer and its other five most highly compensated executive officers:
 
   
                           SUMMARY COMPENSATION TABLE
    
 
   
<TABLE>
<CAPTION>
                                                    ANNUAL COMPENSATION
                                                 --------------------------      ALL OTHER
          NAME AND PRINCIPAL POSITION            YEAR    SALARY      BONUS    COMPENSATION(1)
          ---------------------------            ----   --------    -------   ---------------
<S>                                              <C>    <C>         <C>       <C>
John D. McCown.................................  1996   $235,864(2) $37,311       $   --
  Chairman and Chief Executive Officer
Ralph W. Heim..................................  1996    154,904     64,446        7,625
  President and Chief Operating Officer
J. Edward Morley...............................  1996    112,070     37,311        6,459
  Vice President of Operations
Robert van Dijk................................  1996    108,724     37,311        6,923
  Vice President of Pricing
Mark A. Tanner.................................  1996    104,635     37,311        3,523
  Vice President of Administration
     and Chief Financial Officer
Wayne Hodges...................................  1996    104,183     37,311        3,707
  Vice President of Sales
</TABLE>
    
 
- ---------------
 
(1) Consists of amounts contributed by the Company for the account of the named
    executive under the Company's 401(k) plan and excess group term life
    insurance premiums, respectively, as follows: Mr. Heim, $4,500 and $1,613;
    Mr. Morley, $3,344 and $606; Mr. van Dijk, $3,523 and $965; Mr. Tanner,
    $3,400 and $578; and Mr. Hodges, $3,125 and $582.
   
(2) In 1996 and prior years, Mr. McCown provided services to the Company in
    connection with the Company's vessel charter from its affiliate,
    Kadampanattu Corp. The amount shown as salary on the above table was paid by
    the affiliate. Commencing with the closing of the offering, all of Mr.
    McCown's compensation will be paid directly by the Company, and the
    Company's charter payments will be reduced. See "Certain Transactions."
    
 
CASH BONUS PLAN
 
     The Company has historically paid bonuses to employees from an overall
bonus pool equivalent to 10% of pretax income. Partial bonuses equal to one-half
of the expected amount are distributed on a cumulative quarterly basis, with the
final payment made based on audited annual results. The distribution to
individual employees is determined based on a point system which includes
approximately one-half of the Company's non-driver employees.
 
INCENTIVE STOCK PLAN
 
   
     The Company's Board of Directors and stockholders have adopted an Incentive
Stock Plan designed to attract and retain employees and outside directors and
motivate them through incentives that are aligned with the Company's goals of
increased profitability and stockholder value. The Incentive Stock Plan, the
material terms of which are described below, is intended to afford the Company
wide discretion in making awards. Awards under the Incentive Stock Plan will be
made by the Compensation Committee of the Board of Directors, which will be
formed upon consummation of the offering and will be comprised solely of persons
who qualify as (i) "non-employee directors," as such term is used in Rule 16b-3
under the Securities Exchange Act of 1934, as amended, and (ii) "outside
directors" as defined under Section 162(m) of the Internal Revenue Code (the
"Code"). Awards may be in the form of incentive options or non-qualified
options. An employee who exercises an incentive option will not be required to
recognize taxable income (and the
    
 
                                       40
<PAGE>   42
 
   
Company will not be entitled to a tax deduction) if the employee holds the
shares issued on exercise for the requisite holding period. By contrast, an
employee who exercises a non-qualified option will be required to recognize
taxable income on the date of exercise equal to the spread between the fair
market value of the underlying shares on the date of exercise and the exercise
price, and the Company will be entitled to a corresponding tax deduction.
Incentive options will be designed to comply with applicable provisions of the
Code, including a requirement that exercise prices be equal to at least 100% of
the fair market value of the Common Stock on the date of grant and a ten-year
restriction on the option term. Options for more than 235,500 shares may not be
awarded to any individual during any 12-month period.
    
 
   
     The Company has reserved 785,000 shares of Common Stock for issuance
pursuant to the Incentive Stock Plan, and has awarded non-qualified options to
executives covering an aggregate of 392,500 shares at an exercise price equal to
the initial public offering price of the Common Stock, as follows: Mr. Heim,
137,375 shares; and Messrs. Hodges, Morley, Tanner, van Dijk and Gotimer, 51,025
shares each. Such options become exercisable at the rate of 20% per year
beginning on the first anniversary date of the offering. The Board of Directors
has granted nonqualified options to purchase 78,500 additional shares to 48
other employees at an exercise price equal to the initial public offering price.
Options that expire unexercised or are forfeited become available again for
issuance under the Incentive Stock Plan. Unvested options will become
exercisable in full upon a "change of control," as defined in the award
agreements. The Compensation Committee to be established after the offering may
determine when and in what amounts future awards vest and options become
exercisable. Terms of awards need not be the same for all participants. The
price payable upon exercise of an option may be satisfied in cash or, in the
Committee's discretion, with previously acquired shares of Common Stock.
    
 
401(K) PROFIT SHARING PLAN
 
   
     The Company maintains a defined contribution plan (the "401(k) Plan"),
which is intended to satisfy the tax qualification requirements of the Code. All
Company personnel age 18 or older are eligible to participate in the 401(k) Plan
after one year of service with the Company. The 401(k) Plan permits participants
to contribute up to 15% of their annual compensation from the Company, subject
to the limit imposed by the Code. All amounts deferred under the 401(k) Plan by
a participant fully vest immediately. The 401(k) Plan provides for matching
contributions by the Company at a rate not in excess of 3.0% of compensation and
also permits discretionary contributions. The Company contributed $142,994 to
the 401(k) Plan in 1996. Amounts contributed by the Company vest 20% each year
from the second through the sixth year after contribution. The Company has no
defined benefit or actuarial plans.
    
 
COMPENSATION COMMITTEE INTERLOCKS AND INSIDER PARTICIPATION
 
   
     The Company's Compensation Committee to be established following the
completion of the offering will be comprised of the Company's two independent
directors. Prior to the offering, Malcom P. McLean and John D. McCown made all
decisions concerning executive officer compensation. Mr. McLean is the sole
stockholder and Mr. McCown is the President and Chief Executive Officer of
Kadampanattu Corp., which charters the two vessels currently used by the
Company. See "Certain Transactions."
    
 
DIRECTORS' COMPENSATION
 
     After this offering, each non-employee director will receive an annual
retainer of $5,000 and $1,000 for each meeting of the Board of Directors or
committee of the Board of Directors attended by such director (if such committee
meeting is held other than on the day of a Board meeting), plus reimbursement of
expenses incurred in attending such meetings.
 
                                       41
<PAGE>   43
 
                              CERTAIN TRANSACTIONS
 
   
     The Company charters two roll-on/roll-off barge vessels and the right to
use related ramp structures in Jacksonville, Florida and San Juan, Puerto Rico
from Kadampanattu Corp. ("K Corp"), which is wholly owned by Malcom P. McLean,
the Company's founder, controlling stockholder and a director. The charters
currently provide for a per vessel payment to K Corp of $10,500 per day and also
require the Company to maintain and repair the vessels and ramps. The charters
expire at the later of September 1, 2010 or the repayment of all obligations
under K Corp's construction loan for the 1996 mid-body expansion program. Such
obligations are scheduled to be repaid in quarterly installments ending June 30,
2003. Upon the expiration of the charters, the Company has the option to extend
the charters for an additional eight years at $11,000 per day per vessel, or may
purchase the vessels at their then fair market value. Total expense under these
charters from K Corp was $3.6 million, $3.6 million and $5.9 million in 1994,
1995 and 1996, respectively. The charter payments were increased from $5,000 per
day per vessel in 1996 following completion of the mid-body expansion. In the
opinion of the Board of Directors, the terms of the charters are at least as
favorable as those that could be obtained from unaffiliated third parties.
    
 
   
     K Corp has also provided the Company with the services of Messrs. McCown
and Gotimer pursuant to the charter arrangements and, accordingly, K Corp has
borne the entire salary expense attributable to such officers' services. See
"Management -- Executive Compensation." Effective with the offering, Mr. McCown
will become an employee of the Company, and the daily charter fee payable by the
Company will be reduced from $10,500 to $10,050 per vessel. In addition, the
Company has agreed to pay Mr. Gotimer an annual salary of $50,000 for his legal
services. The reduction in charter fees offsets the Company's compensation
expense for Messrs. McCown and Gotimer after the offering. Accordingly, giving
retroactive effect to these arrangements would not result in a pro forma
increase in the Company's expenses.
    
 
   
     During 1991, 1992 and early 1993, K Corp advanced funds to the Company. K
Corp also agreed to defer receipt of certain charter payments due for 1992. The
advances were used by the Company to fund various construction projects and
general and administration expenses. The advances are represented by a
promissory note, which bears interest at 8% and is due on December 31, 1997 (the
"Note"). The highest outstanding principal balance on the Note during 1994, 1995
and 1996 was $15.4 million, $12.4 million and $7.8 million, respectively, and
the total outstanding principal balance at December 31, 1994, 1995 and 1996 was
$12.4 million, $7.8 million and $4.6 million, respectively. The 1996 amount also
reflects a credit of $1.7 million for substitute vessel costs paid by the
Company while the K Corp vessels were undergoing renovations as part of the
mid-body insertion project. In 1997, the Note was increased by $1.5 million to
reflect an advance made by K Corp to fund the Company's down payment on the two
Triplestack Box Carriers(TM). Approximately $6.2 million of the net proceeds of
the offering will be used to repay the Note in full, including accrued interest.
See "Use of Proceeds."
    
 
   
     The Company has guaranteed the $26.5 million term loan obtained by K Corp
for the 1996 mid-body expansion of the vessels chartered to the Company. The
lender has indicated its intention to release the Company from this guarantee
contingent upon the offering, although as of the date of this Prospectus it is
not contractually obligated to do so. Such loan is scheduled to be repaid in
quarterly installments ending June 30, 2003 (currently $750,000 per quarter,
increasing to $1,250,000 per quarter on June 30, 2001). The outstanding amount
of the loan at March 31, 1997 was $24.2 million. The loan is also secured by a
mortgage on K Corp's vessels and a lien on the related ramp structures. The
aggregate of the latest appraised values of the vessels and related ramps that
secure this indebtedness is $63 million.
    
 
   
     The Company has long term debt arrangements and lease obligations which are
guaranteed by K Corp and which contain financial covenants that require the
Company and K Corp, on a combined basis, to maintain certain financial ratios
which are calculated as of the end of each fiscal quarter. The Company and K
Corp were in compliance with such covenants at March 31, 1997. The aggregate
    
 
                                       42
<PAGE>   44
 
   
amount of such obligations guaranteed by K Corp at December 31, 1996 was $9.2
million. See Note 7 to the Financial Statements. The Company intends to seek
release of such guaranties contingent upon this offering.
    
 
   
     The Company will continue a policy that any transactions with affiliated
persons or entities will be on terms no less favorable to the Company than those
that could have been obtained on an arms-length basis from unaffiliated third
parties. Any such future transactions must also be approved by a majority of the
disinterested directors.
    
 
                             PRINCIPAL STOCKHOLDERS
 
   
     The following table sets forth information regarding the beneficial
ownership of the Common Stock as of the date of this Prospectus, and as adjusted
to reflect the sale of the shares of Common Stock offered hereby, by each person
known by the Company to beneficially own more than 5% of the outstanding shares
of Common Stock; each of the Company's directors and executive officers
identified in the Summary Compensation Table who beneficially owns any Common
Stock; and all directors and executive officers as a group. Unless otherwise
indicated, each of the stockholders has sole voting and investment power with
respect to the shares beneficially owned. The Company has two stockholders of
record at the date of this Prospectus.
    
 
   
<TABLE>
<CAPTION>
                                                                               PERCENT
                                                                       -----------------------
                                                           NUMBER       BEFORE        AFTER
NAME AND ADDRESS                                          OF SHARES    OFFERING    OFFERING(1)
- ----------------                                          ---------    --------    -----------
<S>                                                       <C>          <C>         <C>
Malcom P. McLean(2).....................................  5,338,000      80.0%        56.9%
Clara L. McLean(2)......................................  1,334,500      20.0         14.2
John D. McCown(2).......................................  1,334,500(3)   20.0         14.2
All directors and executive officers as a group (8)
  persons)..............................................  5,338,000      80.0         56.9
</TABLE>
    
 
- ---------------
 
(1) Excludes shares subject to options granted to executive officers under the
    Company's Incentive Stock Plan which become exercisable 20% per year
    beginning on the first anniversary date of the offering.
   
(2) The address of each of the individuals listed above is 500 Park Avenue, 5th
    Floor, New York, NY 10022.
    
   
(3) Consists of shares subject to immediately exercisable options granted by
    Malcom P. McLean to Mr. McCown in February 1994 and May 1997. The February
    1994 options cover 392,500 shares with an exercise price of $.001 per share
    and the May 1997 options cover 942,000 shares with an exercise price of $.95
    per share.
    
 
                                       43
<PAGE>   45
 
                          DESCRIPTION OF CAPITAL STOCK
 
GENERAL
 
   
     The Company is authorized to issue up to 20,000,000 shares of Common Stock,
$.01 value per share, and 1,000,000 shares of preferred stock, $.01 par value
per share. At the date of this Prospectus 6,672,500 shares of Common Stock and
no shares of preferred stock were issued and outstanding. All of the outstanding
Common Stock is, and the shares of Common Stock offered by the Company hereby
when issued and paid for will be, fully paid and non-assessable.
    
 
COMMON STOCK
 
     Voting.  Holders of Common Stock are entitled to one vote per share. All
actions submitted to a vote of stockholders are voted on by holders of Common
Stock voting together as a single class. Holders of Common Stock are not
entitled to cumulative voting in the election of directors.
 
     Dividends.  Holders of Common Stock are entitled to receive dividends
payable in cash or property other than Common Stock on an equal basis, if and
when such dividends are declared by the Board of Directors from funds legally
available, subject to any preference in favor of outstanding shares of preferred
stock, if any.
 
     Liquidation.  In the event of liquidation, holders of Common Stock
participate on a ratable basis in the net assets of the Company available for
distribution after payment or provision for liabilities of the Company and
payment of the liquidation preference, if any, on any outstanding shares of
preferred stock.
 
     Other Terms.  Holders of Common Stock are not entitled to preemptive rights
and the Common Stock is not subject to redemption.
 
     The rights, preferences, and privileges of holders of Common Stock are
subject to, and may be adversely affected by, the rights of the holders of
shares of any series of preferred stock which the Company may designate and
issue in the future.
 
PREFERRED STOCK
 
   
     The Board of Directors is authorized to issue, from time to time and
without approval of the stockholders, up to 1,000,000 shares of preferred stock
in one or more series. The Board of Directors may fix for each series (i) the
distinctive serial designation and number of shares of the series; (ii) the
voting powers and the right, if any, to elect a director or directors (and the
terms of office of any such directors); (iii) the dividend rights, if any; (iv)
the terms of redemption, and the amount of and provisions regarding any sinking
fund for the purchase or redemption thereof; (v) the liquidation preferences and
the amounts payable on dissolution or liquidation; (vi) the terms and conditions
under which shares of the series may or shall be converted into any other series
or class of stock or debt of the Company; and (vii) and any other terms or
provisions which the Board of Directors is legally authorized to fix or alter.
    
 
   
     It is not possible to state the actual effect of the authorization of the
preferred stock upon the rights of holders of the Common Stock until the Board
determines the specific rights of the holders of any series of preferred stock.
Depending upon the rights granted to any series of preferred stock, issuance
thereof could adversely affect the voting power, liquidation rights, or other
rights of the holders of Common Stock or other preferred stock. The Board's
authority to issue shares of preferred stock provides a potential vehicle for
use in possible acquisitions and other corporate purposes, including in
connection with a stockholder rights plan. Any such issuance could have the
effect of making it more difficult for a third party to acquire, or of
discouraging a third party from acquiring, control of the Company. The Company
has no present plans to issue any shares of preferred stock.
    
 
                                       44
<PAGE>   46
 
FOREIGN OWNERSHIP RESTRICTIONS
 
   
     The Company's Certificate of Incorporation ("Certificate") (i) contains
provisions limiting the aggregate percentage ownership by Non-Citizens of the
Company's capital stock (including the Common Stock) to 24.99% of the
outstanding shares (the "Permitted Percentage"), and no more than the Permitted
Percentage of the voting power of the Company, to ensure that such foreign
ownership will not exceed the maximum percentage permitted by applicable federal
law (presently 25.0%); (ii) requires institution of a dual stock certificate
system to help determine such ownership, and (iii) permits the Board of
Directors to make such determinations as may reasonably be necessary to
ascertain such ownership and implement such limitations. These provisions are
intended to protect the Company's ability to operate its vessels in the U.S.
domestic trade governed by the Jones Act. The ability of the Company to so
operate is necessary to avoid default under certain of the Company's financings,
may enhance the Company's ability to incur additional debt, and may have other
effects upon the Company. See "Risk Factors -- Restriction on Foreign Ownership
and Possible Required Divestiture of Stock." The Certificate permits the Board
of Directors to revoke any or all of the foreign ownership restrictions
described herein if the Board, in its discretion, determines that compliance
with the citizenship requirements of the Jones Act, or any or all of such
restrictions, are not in the best interest of the Company.
    
 
   
     To provide a method to enable the Company reasonably to determine stock
ownership by Non-Citizens, the Certificate requires the Company to institute
(and to implement through the transfer agent for the Common Stock) a dual stock
certificate system, pursuant to which certificates representing shares of Common
Stock will bear legends that designate such certificates as either "citizen" or
"non-citizen," depending on the citizenship of the owner. The Company may also
issue non-certificated shares through depositories if the Company determines
such depositories have established procedures that allow the Company to monitor
the ownership of Common Stock by Non-Citizens.
    
 
   
     For purposes of the dual stock certificate system, a "Non-Citizen" is
defined as any person other than a Citizen, and a "Citizen" is defined as: (i)
any individual who is a citizen of the U.S. by birth, naturalization, or as
otherwise authorized by law; (ii) any corporation (a) organized under the laws
of the U.S., or a state, territory, district, or possession thereof, (b) of
which title to not less than 75% of its stock is beneficially owned by and
vested in Citizens, free from any trust or fiduciary obligation in favor of
Non-Citizens, (c) of which not less than 75% of the voting power is vested in
Citizens, free from any contract or understanding through which it is arranged
that such voting power may be exercised directly or indirectly on behalf of
Non-Citizens, (d) of which there are no other means by which control is
conferred upon or permitted to be exercised by Non-Citizens, (e) whose president
or chief executive officer, chairman of the board of directors and all officers
authorized to act in their absence or disability are Citizens, and (f) of which
more than 50% of that number of its directors necessary to constitute a quorum
are Citizens; (iii) any partnership (a) organized under the laws of the U.S., or
a state, territory, district, or possession thereof, (b) all general partners of
which are Citizens, and (c) of which not less than a 75% interest is
beneficially owned and controlled by, and vested in, Citizens, free and clear of
any trust or fiduciary obligation in favor of Non-Citizens; (iv) any association
(a) organized under the laws of the U.S., or a state, territory, district, or
possession thereof, (b) of which 100% of the members are Citizens, (c) whose
president, chief executive officer, or equivalent position, chairman of the
board of directors, or equivalent committee or body, and all persons authorized
to act in their absence or disability are Citizens, (d) of which not less than
75% of the voting power is beneficially owned by Citizens, free and clear of any
trust or fiduciary obligation in favor of Non-Citizens, and (e) of which more
than 50% of that number of its directors or equivalent persons necessary to
constitute a quorum are Citizens; (v) any limited liability company (a)
organized under the laws of the U.S., or a state, territory, district or
possession thereof, (b) of which not less than 75% of the membership interests
are beneficially owned by and vested in Citizens, free from any trust or
fiduciary obligation in favor of Non-Citizens, and the remaining membership
interests are beneficially owned by and vested in persons meeting the
    
 
                                       45
<PAGE>   47
 
   
requirements of 46 U.S.C. Sec. 12102 (a), (c) of which not less than 75% of the
voting power is vested in Citizens, free from any contract or understanding
through which it is arranged that such voting power may be exercised directly or
indirectly on behalf of Non-Citizens, (d) of which there are no other means by
which control is conferred upon or permitted to be exercised by Non-Citizens,
(e) whose president or other chief executive officer or equivalent position,
chairman of the board of directors or equivalent committee or body, managing
members (or equivalent), if any, and all persons authorized to act in their
absence or disability are citizens, free and clear of any trust or fiduciary
obligation in favor of any Non-Citizens, and (f) of which more than 50% of that
number of its directors or equivalent persons necessary to constitute a quorum
are Citizens; (vi) any joint venture, if not an association, corporation,
partnership, or limited liability company (a) organized under the laws of the
U.S., or a state, territory, district, or possession thereof, and (b) of which
100% of the equity is beneficially owned and vested in Citizens, free and clear
of any trust or fiduciary obligation in favor of any Non-Citizens; and (vii) any
trust (a) domiciled in and existing under the laws of the U.S., or a state,
territory, district, or possession thereof, (b) the trustee of which is a
Citizen, and (c) of which not less than a 75% interest is held for the benefit
of Citizens, free and clear of any trust or fiduciary obligation in favor of any
Non-Citizens; and (viii) any other entity not specifically listed above which
the Board of Directors reasonably determines is a "Citizen" consistent with the
foregoing definitions and the Jones Act. The foregoing definition is applicable
at all tiers of ownership and in both form and substance at each tier of
ownership. The Board of Directors is specifically authorized to make reasonable
determinations and interpretations of terms used in the Certificate in defining
a "Citizen" to assure compliance with the Jones Act in accordance with
applicable law and the Certificate. The Board of Directors also may, but is not
required to, exempt any person from classification as a "Non-Citizen" if the
Board determines, based on evidence it deems appropriate, that doing so would
not cause the Company to cease being in compliance with the Jones Act and
applicable law.
    
 
   
     Shares of Common Stock are transferable to Citizens at any time and are
transferable to Non-Citizens if, at the time of such transfer, the transfer
would not increase the aggregate ownership by Non-Citizens, or the aggregate
voting power of Non-Citizens, above the Permitted Percentage in relation to the
total outstanding shares and the total voting power of the Company. Non-Citizen
certificates may be converted to Citizen certificates upon a showing,
satisfactory to the Company, that the holder is a Citizen. Any purported
transfer to Non-Citizens of shares or of an interest in shares of the Company
represented by a Citizen certificate in excess of the Permitted Percentage will
be ineffective as against the Company for all purposes (including for purposes
of voting, dividends, and any other distribution, upon liquidation or
otherwise). In addition, the shares may not be transferred on the books of the
Company, and the Company, whether or not such stock certificate is validly
issued, may refuse to recognize the holder thereof as a stockholder of the
Company except to the extent necessary to effect any remedy available to the
Company. Subject to the foregoing limitations, upon surrender of any stock
certificate for transfer, the transferee will receive citizen certificates or
non-citizen certificates, as applicable.
    
 
   
     The Certificate establishes procedures with respect to the transfer of
shares to enforce the limitations referred to above and authorize the Board of
Directors to implement such procedures. The Board of Directors may take other
actions or make interpretations of the Company's foreign ownership policy as it
deems necessary in order to implement the policy. Pursuant to the procedures
established in the Certificate, as a condition precedent to each issuance and/or
transfer of stock certificates representing shares of Common Stock (including
the shares of Common Stock being sold in the offering), a citizenship
certificate may be required from all transferees (and from any recipient upon
original issuance) of Common Stock and, with respect to the beneficial owner of
the Common Stock being transferred, if the transferee (or the original
recipient) is acting as a fiduciary or nominee for such beneficial owner. The
registration of the transfer (or original issuance) will be denied upon refusal
to furnish such citizenship certificate, which must provide information about
the purported transferee's or beneficial owner's citizenship. Furthermore, as
part of the dual stock certificate system, depositories holding shares of the
Company's Common Stock will be required to
    
 
                                       46
<PAGE>   48
 
   
maintain separate accounts for "Citizen" and "Non-Citizen" shares. When the
beneficial ownership of such shares is transferred, the depositories'
participants will be required to advise such depositories as to the account in
which the transferred shares should be held. In addition, to the extent
necessary to enable the Company to determine the number of shares owned by
Non-Citizens, the Company may from time to time require record holders and
beneficial owners of shares of Common Stock to confirm their citizenship status
and may, in the discretion of the Board of Directors, temporarily withhold
dividends payable to, and deny voting rights to, any such record holder or
beneficial owner until confirmation of citizenship is received.
    
 
   
     Should the Company (or its transfer agent for the Common Stock) become
aware that the ownership by Non-Citizens of Common Stock at any time exceeds the
Permitted Percentage (the "Excess Shares"), the Board of Directors is authorized
to withhold dividends and other distributions temporarily on the Excess Shares,
pending the transfer of such shares to a Citizen or the reduction in the
percentage of shares owned by Non-Citizens to or below the Permitted Percentage,
and to deny voting rights with respect to the Excess Shares. If dividends and
distributions are to be withheld, they will be set aside for the account of the
Excess Shares. At such time as such shares are transferred to a Citizen or the
ownership of such shares by Non-Citizens will not result in aggregate ownership
by Non-Citizens in excess of the Permitted Percentage, the dividends withheld
shall be paid to the then record holders of the related shares. Excess Shares
shall, so long as the excess exists, not be deemed to be outstanding for
purposes of determining the vote required on any matter brought before the
stockholders for a vote. The Certificate provides that the Board of Directors
has the power, in its reasonable discretion and based upon the records
maintained by the Company's transfer agent, to determine those shares of Common
Stock that constitute the Excess Shares. Such determination will be made by
reference to the date or dates on which such shares were purchased by
Non-Citizens, starting with the most recent acquisition of shares by a
Non-Citizen and including, in reverse chronological order, all other
acquisitions of shares by Non-Citizens from and after the acquisition that first
caused the Permitted Percentage to be exceeded; provided that Excess Shares
resulting from a determination that a record holder or beneficial owner is no
longer a Citizen will be deemed to have been acquired as of the date of such
determination. To satisfy the Permitted Percentage described above, the
Certificate authorizes the Board of Directors, in its discretion, to redeem
(upon written notice) Excess Shares in order to reduce the aggregate ownership
by Non-Citizens to the Permitted Percentage. As long as the shares of Common
Stock offered hereby continue to be authorized for quotation on the Nasdaq
National Market, the redemption price will be the average of the closing sale
price of the shares (as reported by the Nasdaq National Market) during the 30
trading days next preceding the date of the notice of redemption. The redemption
price for Excess Shares will be payable in cash. In the event the Company is not
permitted by applicable law to make such redemption or the Board of Directors,
in its discretion, elects not to make such redemption, the Company may direct
the holder of Excess Shares to sell all such Excess Shares for cash in such
manner as the Board of Directors directs.
    
 
CERTAIN PROVISIONS OF CERTIFICATE AND BYLAWS
 
   
     Provisions with Anti-Takeover Implications.  Certain provisions of the
Company's Certificate and Bylaws deal with matters of corporate governance and
the rights of stockholders. Under the Company's Certificate, the Board of
Directors may issue shares of preferred stock and set the voting rights,
preferences, and other terms thereof. The Bylaws provide that a special meeting
of stockholders may be called only by the Chairman of the Board or a majority of
the directors. Such provisions could be deemed to have an anti-takeover effect
and discourage takeover attempts not first approved by the Board of Directors
(including takeovers which certain stockholders may deem to be in their best
interest). Any such discouraging effect upon takeover attempts could potentially
depress the market price of the Common Stock or inhibit temporary fluctuations
in the market price of the Common Stock that otherwise could result from actual
or rumored takeover attempts.
    
 
                                       47
<PAGE>   49
 
   
     Indemnification and Limitation of Liability.  Under its Certificate, the
Company may indemnify, to the full extent permitted by Delaware law, its
directors, officers and employees who are a party, or are threatened to be made
a party, to an action or proceeding, by reason of the fact that the person
serves or served the Company as a director, officer or employee. The Company
also is authorized to purchase insurance and enter into indemnification
agreements whereby it agrees to otherwise grant broader indemnification rights.
The Company intends to enter into indemnification agreements with its executive
officers and directors and purchase directors' and officers' liability insurance
coverage on their behalf. The Certificate also eliminates the liability of
directors and officers to the Company or its stockholders for monetary damages
for breach of fiduciary duty except to the extent such exemption from liability
or limitation thereof is not permitted under applicable law. This provision does
not eliminate the duty of care or loyalty and, in appropriate circumstances,
equitable remedies such as injunctive or other forms of non-monetary relief will
remain available under Delaware law. In addition, each director continues to be
subject to liability for monetary damages for acts or omissions involving breach
of the duty of loyalty, acts or omissions not in good faith, intentional
misconduct, knowing violations of law, unlawful distributions and any
transaction from which the director derived an improper personal benefit. The
Company believes that these provisions of its Certificate and Bylaws are
necessary to attract and retain qualified persons as directors and officers.
    
 
DELAWARE BUSINESS COMBINATION STATUTE
 
   
     Section 203 of the Delaware General Corporation Law ("Section 203")
provides that, subject to certain exceptions specified therein, an interested
stockholder of a Delaware corporation shall not engage in any business
combination with the corporation for a three-year period following the date that
such stockholder becomes an interested stockholder unless (i) prior to such
date, the board of directors of the corporation approved either the business
combination or the transaction which resulted in the stockholder becoming an
interested stockholder, (ii) upon consummation of the transaction which resulted
in the stockholder becoming an interested stockholder, the interested
stockholder owned at least 85% of the voting stock of the corporation
outstanding at the time the transaction commenced (excluding certain shares), or
(iii) on or subsequent to such date, the business combination is approved by the
board of directors of the corporation and authorized at an annual or special
meeting of stockholders by the affirmative vote of at least 66 2/3% of the
outstanding voting stock which is not owned by the interested stockholder.
Except as otherwise specified in Section 203, an interested stockholder is
defined to include (x) any person that is the owner of 15% or more of the
outstanding voting stock of the corporation, or is an affiliate or associate of
the corporation, and was the owner of 15% or more of the outstanding voting
stock of the corporation at any time within three years immediately prior to the
relevant date, and (y) the affiliates and associates of any such person.
    
 
   
     Under certain circumstances, Section 203 makes it more difficult for a
person who would be an interested stockholder to effect various business
combinations with a corporation for a three-year period, although the
stockholders may elect to exclude a corporation from the restrictions imposed
thereunder. The Certificate does not exclude the Company from the restrictions
imposed under Section 203. The provisions of Section 203 may encourage companies
interested in acquiring the Company to negotiate in advance with the Board of
Directors since the stockholder approval requirement would be avoided if a
majority of the directors then in office approve either the business combination
or the transaction which results in the stockholder becoming an interested
stockholder. Such provisions also may have the effect of preventing changes in
the management of the Company. It is possible that such provisions could make it
more difficult to accomplish transactions which stockholders may otherwise deem
to be in their best interests.
    
 
                                       48
<PAGE>   50
 
TRANSFER AGENT AND REGISTRAR
 
   
     BankBoston, N.A. will be the Transfer Agent and Registrar for the Common
Stock. The address of the Transfer Agent and Registrar is BankBoston, N.A., c/o
Boston EquiServe, Blue Hills Office Park, 150 Royall Street, Canton,
Massachusetts 02021, and its phone number is (617) 575-2000.
    
 
                        SHARES ELIGIBLE FOR FUTURE SALE
 
   
     Upon completion of the offering, the Company will have 9,372,500 shares
outstanding. Of these shares, all 2,700,000 shares sold in the offering will be
freely transferable by persons, other than "affiliates" of the Company, without
further restriction under the Securities Act. The Company and all current
stockholders and executive officers have agreed not to offer, sell or otherwise
dispose of any shares of Common Stock owned (or in the case of the Company,
owned or issuable) by them for 180 days from the commencement of the offering
without the prior written consent of Alex. Brown & Sons Incorporated. Commencing
with the expiration of the 180-day period, the 6,672,500 shares of Common Stock
held by current stockholders of the Company will be eligible for sale without
registration in the public market, subject to Rule 144.
    
 
   
     In general, Rule 144 provides that, subject to its provisions and other
applicable federal and state securities law requirements, any person (or persons
whose shares are aggregated), including any person who may be deemed an
"affiliate" as defined under the Securities Act, who has beneficially owned
shares for at least one year is entitled to sell, within any three-month period,
a number of shares that does not exceed the greater of (i) the average weekly
trading volume of the same class of securities during the four calendar weeks
preceding the filing of notice of the sale with the Securities and Exchange
Commission and (ii) 1% of the same class of securities then outstanding, subject
in each case to certain manner-of-sale provisions, notice requirements and the
availability of current information concerning the Company. A person who is not
deemed an "affiliate" of the Company and who has beneficially owned shares for
at least two years is entitled to sell shares under Rule 144 without regard to
the volume limitations and current public information, manner of sale and notice
requirements described above. Restricted shares will also be eligible for sale
to "qualified institutional buyers" pursuant to Rule 144A under the Securities
Act without regard to the volume limitations contained in Rule 144.
    
 
     Prior to the offering, there has been no public market for the Common Stock
and no determination can be made as to the effect, if any, that the sale or
availability for sale of additional shares of the Common Stock will have on the
market price of the Common Stock prevailing from time to time. Nevertheless,
sales of substantial amounts of the shares in the public market could adversely
affect the market price of the Common Stock and could impair the Company's
ability to raise capital through sale of its equity securities.
 
   
     The Company intends to file a registration statement under the Securities
Act to register shares of Common Stock reserved for issuance under its Incentive
Stock Plan, thus permitting the resale of such shares by non-affiliates in the
public market without restriction under the Securities Act. A total of 785,000
shares (including 471,000 shares subject to outstanding options) are reserved
for issuance under the Incentive Stock Plan.
    
 
                                       49
<PAGE>   51
 
                                  UNDERWRITING
 
     Subject to the terms and conditions of the Underwriting Agreement, the
Underwriters named below (the "Underwriters"), through their Representative,
Alex. Brown & Sons Incorporated, have severally agreed to purchase from the
Company the following respective numbers of shares of Common Stock at the
initial public offering price less the underwriting discounts and commissions
set forth on the cover page of this Prospectus:
 
   
<TABLE>
<CAPTION>
                                                              NUMBER OF
                        UNDERWRITER                            SHARES
                        -----------                           ---------
<S>                                                           <C>
Alex. Brown & Sons Incorporated.............................
 
                                                              ---------
Total.......................................................  2,700,000
                                                              =========
</TABLE>
    
 
     The Underwriting Agreement provides that the obligations of the
Underwriters are subject to certain conditions precedent and that the
Underwriters will purchase all shares of the Common Stock offered hereby if any
of such shares are purchased.
 
     The Company has been advised by the Representative of the Underwriters that
the Underwriters propose to offer the shares of Common Stock to the public at
the initial public offering price set forth on the cover page of this Prospectus
and to certain dealers at such price less a concession not in excess of
$          per share. The Underwriters may allow, and such dealers may reallow,
a concession not in excess of $          per share to certain other dealers.
After the initial public offering, the offering price and other selling terms
may be changed by the Representative of the Underwriters.
 
   
     The Company has granted to the Underwriters an option, exercisable not
later than 30 days after the date of this Prospectus, to purchase up to 405,000
additional shares of Common Stock at the public offering price less the
underwriting discounts and commissions set forth on the cover page of this
Prospectus. To the extent that the Underwriters exercise such option, each of
the Underwriters will have a firm commitment to purchase approximately the same
percentage thereof that the number of shares of Common Stock to be purchased by
it shown in the above table bears to 405,000, and the Company will be obligated,
pursuant to the option, to sell such shares to the Underwriters. The
Underwriters may exercise such option only to cover over-allotments made in
connection with the sale of Common Stock offered hereby. If purchased, the
Underwriters will offer such additional shares on the same terms as those on
which the 2,700,000 shares are being offered.
    
 
     The Company has agreed to indemnify the Underwriters against certain
liabilities, including liabilities under the Securities Act of 1933, as amended.
 
   
     In connection with the offering, certain Underwriters and selling group
members and their respective affiliates may engage in transactions that
stabilize, maintain or otherwise affect the market price of the Common Stock.
Such transactions may include stabilization transactions effected in accordance
with Rule 104 of Regulation M, pursuant to which such persons may bid for or
purchase Common Stock for the purpose of stabilizing its market price. The
Underwriters also may create a short position for the account of the
Underwriters by selling more Common Stock in connection with the offering than
they are committed to purchase from the Company, and in such case may purchase
Common Stock in the open market following completion of the offering to cover
all or a portion of such short position. The Underwriters may also cover all or
a portion of such short position, up to 405,000 shares, by exercising the
Underwriters' over-allotment option referred to above. The Representative, on
behalf of the Underwriters, may impose "penalty bids" under
    
 
                                       50
<PAGE>   52
 
contractual arrangements with the Underwriters whereby it may reclaim from an
Underwriter (or dealer participating in the offering), for the account of the
other Underwriters, the selling concession with respect to the Common Stock that
is distributed in the offering but subsequently purchased for the account of the
Underwriters in the open market. Any of the transactions described in this
paragraph may result in the maintenance of the price of the Common Stock at a
level above that which might otherwise prevail in the open market. None of these
transactions described in this paragraph is required, and, if undertaken, they
may be discontinued at any time.
 
   
     Stockholders and executive officers of the Company, holding in the
aggregate 6,672,500 shares of Common Stock, have agreed not to offer, sell or
otherwise dispose of any of such Common Stock for a period of 180 days after the
date of this Prospectus without the prior consent of the Representatives of the
Underwriters. See "Shares Eligible for Future Sale."
    
 
     The Representative of the Underwriters has advised the Company that the
Underwriters do not intend to confirm sales to any account over which they
exercise discretionary authority.
 
   
     Prior to this offering, there has been no public market for the Common
Stock of the Company. Consequently, the initial public offering price for the
Common Stock will be determined by negotiation between the Company and the
Representative of the Underwriters. Among the factors to be considered in such
negotiations are prevailing market conditions, the results of operations of the
Company in recent periods, the history of and prospects for the Company's
business and the industry in which it competes, current market valuations of
publicly traded corporations that are comparable to the Company, an assessment
of the Company's management and other factors deemed relevant.
    
 
                                 LEGAL MATTERS
 
   
     The validity of the shares of Common Stock offered hereby will be passed
upon for the Company by Foley & Lardner, Jacksonville, Florida. Certain legal
matters in connection with the offering are being passed upon for the
Underwriters by Greenberg Traurig Hoffman Lipoff Rosen & Quentel, P.A., Miami,
Florida.
    
 
                                    EXPERTS
 
     The financial statements as of December 31, 1995 and 1996 and for each of
the three years in the period ended December 31, 1996 included in this
Prospectus and the related financial statement schedule included elsewhere in
the Registration Statement have been audited by Deloitte & Touche LLP,
independent auditors, as indicated in their reports appearing herein and
elsewhere in the Registration Statement, and have been so included herein in
reliance upon the reports of said firm given upon their authority as experts in
accounting and auditing.
 
                                       51
<PAGE>   53
 
                             ADDITIONAL INFORMATION
 
     The Company has filed with the Securities and Exchange Commission (the
"Commission") a Registration Statement on Form S-1 (the "Registration
Statement") under the Securities Act with respect to the Common Stock offered
hereby. This Prospectus, which is part of the Registration Statement, does not
contain all the information set forth in the Registration Statement and the
exhibits and schedules thereto, certain items of which are omitted in accordance
with the rules and regulations of the Commission. For further information with
respect to the Company and the Common Stock, reference is hereby made to the
Registration Statement and such exhibits and schedules filed as a part thereof,
which may be inspected, without charge, at the Public Reference Section of the
Commission at Room 1024, Judiciary Plaza, 450 Fifth Street, N.W., Washington, DC
20549, and at the regional offices of the Commission located at 7 World Trade
Center, Suite 1300, New York, New York 10048 and Citicorp Center, 500 West
Madison Street, Suite 1400, Chicago, Illinois 60661-2511. Copies of all or any
portion of the Registration Statement may be obtained from the Public Reference
Section of the Commission, upon payment of prescribed fees. The Commission also
maintains a Web site that contains reports, proxy and information statements and
other information regarding Registrants, including the Company, that file
electronically with the Commission. The address of such Web site is
http://www.sec.gov.
 
     Statements contained in this Prospectus as to the content of any contract,
agreement, or other document referred to are not necessarily complete, and, in
each instance, reference is made to the copy of such contract, agreement, or
document filed as an exhibit to the Registration Statement, each such statement
being qualified in its entirety by such reference.
 
                                       52
<PAGE>   54
 
                              TRAILER BRIDGE, INC.
 
                         INDEX TO FINANCIAL STATEMENTS
 
   
<TABLE>
<CAPTION>
                                                              PAGE
                                                              ----
<S>                                                           <C>
Independent Auditors' Report................................  F-2
Balance Sheets..............................................  F-3
Statements of Operations....................................  F-4
Statements of Changes in Common Stockholders' Equity
  (Deficit).................................................  F-5
Statements of Cash Flows....................................  F-6
Notes to Financial Statements...............................  F-7
</TABLE>
    
 
                                       F-1
<PAGE>   55
 
                          INDEPENDENT AUDITORS' REPORT
 
To the Board of Directors and Stockholders of
  Trailer Bridge, Inc.
  Jacksonville, Florida
 
     We have audited the accompanying balance sheets of Trailer Bridge, Inc. as
of December 31, 1995 and 1996, and the related statements of operations, common
stockholders' equity, and cash flows for each of the three years in the period
ended December 31, 1996. These financial statements are the responsibility of
the Company's management. Our responsibility is to express an opinion on these
financial statements based on our audits.
 
     We conducted our audits in accordance with generally accepted auditing
standards. Those standards require that we plan and perform the audit to obtain
reasonable assurance about whether the financial statements are free of material
misstatement. An audit includes examining, on a test basis, evidence supporting
the amounts and disclosures in the financial statements. An audit also includes
assessing the accounting principles used and significant estimates made by
management, as well as evaluating the overall financial statement presentation.
We believe that our audits provide a reasonable basis for our opinion.
 
     In our opinion, such financial statements present fairly, in all material
respects, the financial position of Trailer Bridge, Inc. as of December 31, 1995
and 1996, and the results of its operations and its cash flows for each of the
three years in the period ended December 31, 1996 in conformity with generally
accepted accounting principles.
 
                                          Deloitte & Touche LLP
 
Jacksonville, Florida
February 28, 1997
   
(July   , 1997 as to Note 11)
    
 
     The accompanying financial statements reflect the recapitalization of the
Company as described in Note 11 to the financial statements. The above report is
in the form which will be signed by Deloitte & Touche LLP upon completion of
such recapitalization.
 
                                       F-2
<PAGE>   56
 
                              TRAILER BRIDGE, INC.
 
                                 BALANCE SHEETS
 
<TABLE>
<CAPTION>
                                                DECEMBER 31,
                                          -------------------------    MARCH 31,
                                             1995          1996          1997
                                          -----------   -----------   -----------
                                                                      (UNAUDITED)
<S>                                       <C>           <C>           <C>           
                                     ASSETS
CURRENT ASSETS:
  Cash and cash equivalents.............  $   498,328   $ 1,658,921   $ 2,246,206
  Trade receivables, less allowance for
     doubtful accounts of $655,440,
     $905,581 and $1,178,737............    8,909,418     8,305,872     8,252,435
  Prepaid expenses......................      611,229       964,971       343,003
                                          -----------   -----------   -----------
          Total current assets..........   10,018,975    10,929,764    10,841,644
                                          -----------   -----------   -----------
PROPERTY AND EQUIPMENT, net.............    8,851,225    12,512,130    14,348,862
GOODWILL, less accumulated amortization
  of $170,984, $217,763 and $229,458....      997,958       951,179       939,484
OTHER ASSETS............................      357,375       370,592       310,280
                                          -----------   -----------   -----------
          TOTAL ASSETS..................  $20,225,533   $24,763,665   $26,440,270
                                          ===========   ===========   ===========
 
                      LIABILITIES AND STOCKHOLDERS' EQUITY
CURRENT LIABILITIES:
  Accounts payable......................  $ 1,322,044   $ 1,981,421   $ 1,359,062
  Other accrued liabilities.............    2,489,555     2,635,099     3,225,631
  Current portion of notes payable......    2,677,870     3,117,069     2,865,326
  Current portion of capital lease
     obligations........................      122,435        38,197        36,365
  Unearned revenue......................      278,898       223,627       299,881
  Due to affiliate......................    7,825,136     4,653,192     5,878,364
                                          -----------   -----------   -----------
          Total current liabilities.....   14,715,938    12,648,605    13,664,629
NOTES PAYABLE, less current portion.....    2,836,425     5,909,072     6,312,977
CAPITAL LEASE OBLIGATIONS, less current
  portion...............................                    161,444       149,077
                                          -----------   -----------   -----------
          TOTAL LIABILITIES.............   17,552,363    18,719,121    20,126,683
                                          -----------   -----------   -----------
COMMITMENTS (Notes 5, 8 and 10)
</TABLE>
 
   
<TABLE>
<CAPTION>
                                                                                     MARCH 31,
                                                                                       1997
                                                                                     PRO FORMA
                                                                                    -----------
                                                                                    (UNAUDITED)
                                                                                     (NOTE 3)
<S>                                       <C>           <C>           <C>           <C>
 
STOCKHOLDERS' EQUITY (Note 11):
  Preferred stock, $.01 par value,
     1,000,000 shares authorized; no
     shares issued or outstanding.......
  Common stock, $.01 par value,
     20,000,000 shares authorized;
     6,672,500 shares issued and
     outstanding........................       66,725        66,725        66,725      66,725
  Additional paid-in capital............      (66,300)      (66,300)      (66,300)    (66,300)
  Retained earnings.....................    2,672,745     6,044,119     6,313,162     313,162
                                          -----------   -----------   -----------    --------
          Total stockholders' equity....    2,673,170     6,044,544     6,313,587     313,587
                                          -----------   -----------   -----------    --------
          TOTAL LIABILITIES AND
            STOCKHOLDERS' EQUITY........  $20,225,533   $24,763,665   $26,440,270
                                          ===========   ===========   ===========
</TABLE>
    
 
                       See notes to financial statements.
 
                                       F-3
<PAGE>   57
 
                              TRAILER BRIDGE, INC.
 
                            STATEMENTS OF OPERATIONS
 
   
<TABLE>
<CAPTION>
                                                                                      THREE MONTHS
                                             YEARS ENDED DECEMBER 31,                ENDED MARCH 31,
                                      ---------------------------------------   -------------------------
                                         1994          1995          1996          1996          1997
                                      -----------   -----------   -----------   -----------   -----------
                                                                                       (UNAUDITED)
<S>                                   <C>           <C>           <C>           <C>           <C>
OPERATING REVENUES..................  $72,192,336   $62,531,365   $63,148,218   $14,568,079   $16,446,066
OPERATING EXPENSES:
  Salaries, wages and benefits......   19,307,773    14,591,795    13,288,633   3,434,673..     3,404,267
  Rent and purchased transportation:
    Related party...................    3,650,000     3,650,000     5,900,000       910,000     1,890,000
    Other...........................   15,966,059    10,847,200    10,331,461     2,520,047     2,320,837
  Fuel..............................    5,426,143     5,255,979     5,883,378     1,468,256     1,557,433
  Operating and maintenance
    (exclusive of depreciation shown
    separately below)...............   11,781,830    10,553,364    14,210,787     3,045,731     3,205,616
  Taxes and licenses................      960,781       588,565       455,407       138,263       156,237
  Insurance and claims..............    2,202,489     1,860,997     2,121,039       514,040       521,612
  Communications and utilities......      833,840       620,815       607,833       143,284       134,448
  Depreciation and amortization.....    2,646,573     2,761,139     2,944,069       701,283       689,016
  Other operating expenses..........    3,241,356     3,023,161     2,981,104       726,751       818,701
                                      -----------   -----------   -----------   -----------   -----------
                                       66,016,844    53,753,015    58,723,711    13,602,328    14,698,167
                                      -----------   -----------   -----------   -----------   -----------
OPERATING INCOME....................    6,175,492     8,778,350     4,424,507       965,751     1,747,899
NONOPERATING INCOME (EXPENSE):
  Interest expense, net:
    Related party...................   (1,159,702)     (822,558)     (457,743)     (143,182)      (91,400)
    Other...........................     (657,775)     (539,554)     (623,332)     (103,627)     (172,016)
  Gain (loss) on sale of equipment,
    net.............................       12,143        47,834        66,523        (9,173)
                                      -----------   -----------   -----------   -----------   -----------
                                       (1,805,334)   (1,314,278)   (1,014,552)     (255,982)     (263,416)
                                      -----------   -----------   -----------   -----------   -----------
INCOME BEFORE PROVISION AND PRO
  FORMA PROVISION FOR INCOME
  TAXES.............................    4,370,158     7,464,072     3,409,955       709,769     1,484,483
PROVISION FOR INCOME TAXES..........      (11,859)      (67,316)      (38,581)       (7,301)      (29,690)
                                      -----------   -----------   -----------   -----------   -----------
NET INCOME BEFORE PRO FORMA
  PROVISION FOR INCOME TAXES........    4,358,299     7,396,756     3,371,374       702,468     1,454,793
PRO FORMA PROVISION FOR INCOME TAXES
  (Note 3)..........................   (2,015,594)   (3,037,048)   (1,298,442)     (259,647)     (545,530)
                                      -----------   -----------   -----------   -----------   -----------
PRO FORMA NET INCOME (Note 3).......  $ 2,342,705   $ 4,359,708   $ 2,072,932   $   442,821   $   909,263
                                      ===========   ===========   ===========   ===========   ===========
PRO FORMA NET INCOME PER SHARE (Note
  3)................................                              $      0.29                 $      0.13
                                                                  ===========                 ===========
PRO FORMA WEIGHTED AVERAGE SHARES
  OUTSTANDING.......................                                7,172,500                   7,172,500
                                                                  ===========                 ===========
</TABLE>
    
 
                       See notes to financial statements.
 
                                       F-4
<PAGE>   58
 
                              TRAILER BRIDGE, INC.
 
         STATEMENTS OF CHANGES IN COMMON STOCKHOLDERS' EQUITY (DEFICIT)
                YEARS ENDED DECEMBER 31, 1994, 1995 AND 1996 AND
                 (UNAUDITED) THREE MONTHS ENDED MARCH 31, 1997
 
<TABLE>
<CAPTION>
                                                                              RETAINED
                                           COMMON STOCK        ADDITIONAL     EARNINGS
                                       ---------------------    PAID-IN     (ACCUMULATED
                                         SHARES      AMOUNT     CAPITAL       DEFICIT)        TOTAL
                                       ----------   --------   ----------   ------------   -----------
<S>                                    <C>          <C>        <C>          <C>            <C>
BALANCE AT DECEMBER 31, 1993.........   7,850,000   $ 78,500    $(78,000)   $(7,214,813)   $(7,214,313)
  Net income.........................                                         4,358,299      4,358,299
                                       ----------   --------    --------    -----------    -----------
BALANCE AT DECEMBER 31, 1994.........   7,850,000     78,500     (78,000)    (2,856,514)    (2,856,014)
  Repurchase and retirement of
     1,177,500 shares of common
     stock...........................  (1,177,500)   (11,775)     11,700       (517,195)      (517,270)
  Cash dividends ($.20 per share)....                                        (1,350,302)    (1,350,302)
  Net income.........................                                         7,396,756      7,396,756
                                       ----------   --------    --------    -----------    -----------
BALANCE AT DECEMBER 31, 1995.........   6,672,500     66,725     (66,300)     2,672,745      2,673,170
  Net income.........................                                         3,371,374      3,371,374
                                       ----------   --------    --------    -----------    -----------
BALANCE AT DECEMBER 31, 1996.........   6,672,500     66,725     (66,300)     6,044,119      6,044,544
  Cash dividends ($.18 per share)
     (unaudited).....................                                        (1,185,750)    (1,185,750)
  Net income (unaudited).............                                         1,454,793      1,454,793
                                       ----------   --------    --------    -----------    -----------
BALANCE AT MARCH 31, 1997
  (UNAUDITED)........................   6,672,500   $ 66,725    $(66,300)   $ 6,313,162    $ 6,313,587
                                       ==========   ========    ========    ===========    ===========
</TABLE>
 
                       See notes to financial statements.
 
                                       F-5
<PAGE>   59
 
                              TRAILER BRIDGE, INC.
 
                            STATEMENTS OF CASH FLOWS
 
<TABLE>
<CAPTION>
                                                                                                  THREE MONTHS
                                                         YEARS ENDED DECEMBER 31,                ENDED MARCH 31,
                                                  ---------------------------------------   -------------------------
                                                     1994          1995          1996          1996          1997
                                                  -----------   -----------   -----------   -----------   -----------
                                                                                                   (UNAUDITED)
<S>                                               <C>           <C>           <C>           <C>           <C>
OPERATING ACTIVITIES:
  Net income....................................  $ 4,358,299   $ 7,396,756   $ 3,371,374   $   702,468   $ 1,454,793
  Adjustments to reconcile net income to net
    cash provided by operating activities:
    Depreciation and amortization...............    2,646,572     2,761,139     2,944,069       701,283       689,016
    Provision for uncollectible accounts........      515,302       158,995       673,699       106,063       120,413
    (Gain) loss on sale of equipment............      (12,143)      (47,834)      (66,523)        9,173
    Change in assets and liabilities:
      Decrease (increase) in trade
        receivables.............................     (904,486)   (1,282,693)      (70,153)    1,136,321       (66,976)
      Decrease (increase) in prepaid expenses...      728,100       649,459      (353,742)     (346,741)      621,968
      Increase (decrease) in accounts payable...      284,066      (289,355)      659,377       131,411      (622,359)
      Increase (decrease) in accrued
        liabilities.............................       46,434    (1,125,571)      145,544      (242,844)      590,532
      Increase (decrease) in unearned revenue...      137,618       (95,288)      (55,271)      116,946        76,254
                                                  -----------   -----------   -----------   -----------   -----------
        Net cash provided by operating
          activities............................    7,799,762     8,125,608     7,248,374     2,314,080     2,863,641
                                                  -----------   -----------   -----------   -----------   -----------
INVESTING ACTIVITIES:
  Increase (decrease) in due to affiliate.......   (2,930,298)   (4,617,442)   (3,171,944)   (1,725,996)    1,225,172
  Purchases and construction of property and
    equipment...................................   (4,598,587)   (1,430,179)   (6,707,075)      (43,862)   (2,514,053)
  Proceeds from the sale of equipment...........      320,609     1,031,000       426,462         7,150
  (Increase) decrease in other assets...........      (82,643)        7,080       (13,217)      (25,336)       60,312
                                                  -----------   -----------   -----------   -----------   -----------
        Net cash used in investing activities...   (7,290,919)   (5,009,541)   (9,465,774)   (1,788,044)   (1,228,569)
                                                  -----------   -----------   -----------   -----------   -----------
FINANCING ACTIVITIES:
  Proceeds from borrowings on notes payable.....    4,127,158     1,032,500     6,637,569                   1,134,018
  Payments on notes payable.....................   (2,612,244)   (3,410,552)   (3,125,722)     (626,815)     (981,856)
  Payments of dividends.........................                 (1,350,302)                               (1,185,750)
  Payments for repurchase of stock..............                   (517,270)
  Payments on capital lease obligations.........     (578,938)     (318,484)     (133,854)      (24,127)      (14,199)
                                                  -----------   -----------   -----------   -----------   -----------
    Net cash provided by (used in) financing
      activities................................      935,976    (4,564,108)    3,377,993      (650,942)   (1,047,787)
                                                  -----------   -----------   -----------   -----------   -----------
NET INCREASE (DECREASE) IN CASH AND CASH
  EQUIVALENTS...................................    1,444,819    (1,448,041)    1,160,593      (124,906)      587,285
CASH AND CASH EQUIVALENTS, BEGINNING OF
  PERIOD........................................      501,550     1,946,369       498,328       498,328     1,658,921
                                                  -----------   -----------   -----------   -----------   -----------
CASH AND CASH EQUIVALENTS, END OF PERIOD........  $ 1,946,369   $   498,328   $ 1,658,921   $   373,422   $ 2,246,206
                                                  ===========   ===========   ===========   ===========   ===========
SUPPLEMENTAL CASH FLOW INFORMATION AND NONCASH
  INVESTING AND FINANCING ACTIVITIES:
  Amounts paid for state income taxes...........  $     5,154   $    10,524   $    68,035   $     6,629
                                                  ===========   ===========   ===========   ===========
  Amounts paid for interest:
    Related party...............................  $ 1,142,955   $   824,538   $   457,151   $   143,991
    Other.......................................      680,646       632,549       652,554       111,851   $   283,620
                                                  -----------   -----------   -----------   -----------   -----------
                                                  $ 1,823,601   $ 1,457,087   $ 1,109,705   $   255,842   $   283,620
                                                  ===========   ===========   ===========   ===========   ===========
  Equipment acquired under capital lease
    agreements..................................                              $   211,060
                                                                              ===========
</TABLE>
 
                       See notes to financial statements.
 
                                       F-6
<PAGE>   60
 
                              TRAILER BRIDGE, INC.
 
                         NOTES TO FINANCIAL STATEMENTS
                YEARS ENDED DECEMBER 31, 1994, 1995 AND 1996 AND
             (UNAUDITED) THREE MONTHS ENDED MARCH 31, 1996 AND 1997
 
1. ORGANIZATION
 
     Trailer Bridge, Inc. (the "Company") is a domestic trucking and marine
transportation company with contract and common carrier authority. Highway
transportation services are offered primarily in the continental United States,
while marine transportation is offered between Jacksonville, Florida and San
Juan, Puerto Rico.
 
2. SUMMARY OF SIGNIFICANT ACCOUNTING POLICIES
 
     Cash and Cash Equivalents.  For purposes of the statement of cash flows,
the Company considers all highly liquid securities with original maturities of
three months or less to be cash equivalents.
 
   
     Fair Value of Financial Instruments.  The carrying value of the Company's
financial instruments, which include capital lease obligations and notes
payable, approximate fair value based on the borrowing rates currently available
to the Company for capital leases and notes payable with similar terms and
maturities.
    
 
     Use of Estimates.  The preparation of financial statements in conformity
with generally accepted accounting principles requires management to make
estimates and assumptions that affect the reported amounts of assets and
liabilities and disclosure of contingent assets and liabilities at the date of
the financial statements and the reported amounts of revenues and expenses
during the reporting period. Actual results could differ from those estimates.
 
     Allowance for Doubtful Accounts.  The Company provides an allowance for
doubtful accounts on trade receivables based upon estimated collectibility and
collection experience.
 
     Property and Equipment.  Property and equipment are stated at cost less
accumulated depreciation. Property and equipment are depreciated on a
straight-line method based on the following estimated useful lives:
 
<TABLE>
<CAPTION>
                                                              YEARS
                                                              -----
<S>                                                           <C>
Buildings and structures....................................   40
Office furniture and equipment..............................  6-10
Freight equipment...........................................  4-12
Leasehold improvements......................................  2-5
Equipment under capital leases..............................   5
</TABLE>
 
   
     Tires on revenue equipment purchased are capitalized as part of the
equipment cost and depreciated over the life of the vehicle. Replacement tires
are expensed when placed in service.
    
 
     Leasehold improvements and equipment under capital leases are amortized
over the lesser of the estimated lives of the asset or the lease terms.
Maintenance and repairs which do not materially extend useful life and minor
replacements are charged to earnings as incurred.
 
     Goodwill.  Goodwill is being amortized on a straight-line basis over
twenty-five years.
 
     Insurance.  The Company is self-insured for employee medical coverage above
deductible amounts. Reinsurance is obtained to cover losses in excess of certain
limits. Provisions for losses are determined on the basis of claims reported and
an estimate of claims incurred but not reported.
 
   
     Revenue Recognition.  Common carrier operations revenue is recorded on the
percentage-of-completion basis and direct costs are expensed as incurred.
    
 
                                       F-7
<PAGE>   61
 
                              TRAILER BRIDGE, INC.
 
                  NOTES TO FINANCIAL STATEMENTS -- (CONTINUED)
 
     Income Taxes.  The Company is organized under Subchapter S of the Internal
Revenue Code for income tax purposes and therefore, all Federal and certain
state income taxes are the responsibility of the Company's stockholders. The
Company is subject to state income taxes in those states that do not recognize
Subchapter S elections. State income tax expense for 1994, 1995 and 1996 was not
significant due to the utilization of net operating loss carryforwards.
 
NEW ACCOUNTING STANDARDS
 
     Effective January 1, 1996, the Company adopted the provisions of Statement
of Financial Accounting Standards No. 121, "Accounting for the Impairment of
Long-Lived Assets and for Long-Lived Assets to be Disposed of" (SFAS No. 121)
which requires that long-lived assets and certain intangibles to be held and
used by the Company be reviewed for impairment whenever events or changes in
circumstances indicate that the carrying amount of an asset may not be
recoverable. The adoption of SFAS No. 121 did not have a material impact on the
Company.
 
     Effective January 1, 1996, the Company adopted Statement of Financial
Accounting Standards No. 123, "Accounting for Stock-Based Compensation" (SFAS
No. 123). SFAS 123 establishes a fair value based method of accounting for
stock-based employee compensation plans; however, it also allows an entity to
continue to measure compensation cost for those plans using the intrinsic value
based method of accounting prescribed by Accounting Principles Board ("APB")
Opinion No. 25, "Accounting for Stock Issued to Employees". Under the fair value
based method, compensation cost is measured at the grant date based on the value
of the award and is recognized over the service period, which is usually the
vesting period. The Company has elected to account for its employee stock
compensation plan under APB Opinion No. 25 with pro forma disclosures of net
earnings and earnings per share, as if the fair value based method of accounting
defined in SFAS No. 123 has been applied.
 
     In March 1997, the Financial Accounting Standards Board issued Statement of
Financial Accounting Standards No. 128, "Earnings per Share." This Statement
establishes standards for computing and presenting earnings per share ("EPS")
and applies to all entities with publicly held common stock or potential common
stock. This Statement replaces the presentation of primary EPS and fully diluted
EPS with a presentation of basic EPS and diluted EPS, respectively. Basic EPS
excludes dilution and is computed by dividing earnings available to common
stockholders by the weighted-average number of common shares outstanding for the
period. Similar to fully diluted EPS, diluted EPS reflects the potential
dilution of securities that could share in the earnings. This Statement is not
expected to have a material effect on the Company's reported EPS amounts. This
Statement is effective for the Company's financial statements for the year ended
December 31, 1997.
 
3. INTERIM AND PRO FORMA INFORMATION
 
     Unaudited Interim Information.  The financial information with respect to
the three-month periods ended March 31, 1996 and 1997 is unaudited. The results
of operations for the three-month period ended March 31, 1997 are not
necessarily indicative of the results to be expected for the full year. In the
opinion of management, such information contains all adjustments, consisting
only of normal recurring adjustments, necessary for a fair presentation of the
results of such periods.
 
     Pro Forma Adjustments.  The Company is organized under Subchapter S of the
Internal Revenue Code. The Company has not been subject to Federal income taxes
and state income tax expense has not been significant due to the utilization of
net operating loss carryforwards. Prior to the closing of the proposed public
offering, the Company will terminate its status as an S Corporation. The pro
forma adjustments reflect a provision for income taxes that would have been
incurred had the Company not been organized under Subchapter S of the Internal
Revenue Code.
 
                                       F-8
<PAGE>   62
 
                              TRAILER BRIDGE, INC.
 
                  NOTES TO FINANCIAL STATEMENTS -- (CONTINUED)
 
The effective rate differs from the Federal statutory rate of 34% due to state
income taxes (net of Federal income tax benefits), amortization of goodwill and
other nondeductible expenses and due to the utilization of the net operating
loss carryforwards of a business acquired in 1992. The pro forma statement of
operations data do not give effect to the one-time, non-cash charge of
approximately $650,000 in recognition of deferred income taxes resulting from
the termination of the Company's S Corporation status upon the effectiveness of
the Company's proposed stock offering.
 
     Pro Forma Stockholders' Equity.  The Company intends to declare a dividend
payable to existing stockholders in the aggregate amount of $6 million. Such
dividend will be paid with a portion of the net proceeds of the Company's
proposed stock offering. Upon completion of the proposed stock offering, the
remaining retained earnings will be reclassified to additional paid-in capital.
 
   
     Pro Forma Net Income Per Share.  Pro forma net income per share reflects a
15,700-for-1 stock split that will become effective in connection with the
proposed stock offering and the issuance of 500,000 shares of common stock to
fund the payment of a $6.0 million S Corporation dividend to the Company's
existing stockholders with a portion of the net proceeds of this offering.
    
 
   
     Supplementary Pro Forma Net Income Per Share.  The Company expects to use a
portion of the proceeds from its initial public offering to repay amounts due to
affiliate. Pro forma net income per share adjusted for the interest savings and
the issuance of approximately 652,000 shares of Common Stock to fund the
repayment, assuming the issuance and repayment had occurred on January 1, 1996
would have been $0.30 and $0.12 for the year ended December 31, 1996 and the
three months ended March 31, 1997, respectively.
    
 
4. PROPERTY AND EQUIPMENT
 
     Property and equipment consist of the following:
 
<TABLE>
<CAPTION>
                                                    DECEMBER 31,
                                              -------------------------    MARCH 31,
                                                 1995          1996          1997
                                              -----------   -----------   -----------
<S>                                           <C>           <C>           <C>
Land........................................  $             $   504,703   $   504,703
Construction in progress....................                     90,512     1,601,450
Buildings and structures....................       89,005     1,137,127     1,137,127
Office furniture and equipment..............    1,088,937     1,058,381     1,060,269
Freight equipment...........................   12,444,515    16,726,428    16,507,080
Leasehold improvements......................      716,347       712,798       712,799
Equipment under capital leases..............      365,540       536,495       536,495
Less accumulated depreciation and
  amortization..............................   (5,853,119)   (8,254,314)   (7,711,061)
                                              -----------   -----------   -----------
Property and equipment, net.................  $ 8,851,225   $12,512,130   $14,348,862
                                              ===========   ===========   ===========
</TABLE>
 
     Depreciation and amortization expense on property and equipment and
equipment under capital leases was $2,599,793, $2,714,360 and $2,897,290 in
1994, 1995 and 1996, respectively, and was $689,588 and $677,321 for the three
months ended March 31, 1996 and 1997, respectively.
 
                                       F-9
<PAGE>   63
 
                              TRAILER BRIDGE, INC.
 
                  NOTES TO FINANCIAL STATEMENTS -- (CONTINUED)
 
5. TRANSACTIONS WITH AFFILIATED COMPANY
 
     Due to Affiliate.  Amounts due to affiliate include cash advanced to the
Company from an affiliated company to fund various construction projects,
general and administrative expenses, interest payable on such cash advances and
barge rent. The advances bear interest at 8% and are due on December 31, 1997.
The affiliated company has indicated that it is willing to extend the payment
date of such notes for another term of one year in the event that the Company is
unable to pay such amounts on December 31, 1997. Management of the Company
believes that such indebtedness will be repaid through a combination of cash
flows from future operations with such debt to be refinanced on a long-term
basis and from the proceeds of equity offerings.
 
   
     Lease Agreements.  The Company leases two roll-on/roll-off barge vessels
and a ramp system from an affiliate under operating lease agreements. For the
period from January 1, 1994 through May 10, 1996 for one vessel and through July
19, 1996, as to the other vessel, the lease payment was $5,000 per day for each
vessel. Upon completion of the renovations to the vessels during 1996 which
extended the barges from a length of approximately 500 feet to a length of
approximately 750 feet, the lease payments were increased to $10,500 per day for
each vessel. The leases expire at the later of September 1, 2010 or the
repayment of all obligations under an affiliate's construction loan related to
the vessel renovations, which payment has been guaranteed by the Company. Such
construction loan is scheduled to be repaid in quarterly installments ending
June 30, 2003. The leases provide the Company the option to extend the leases
through September 1, 2018 for total payments of $11,000 per vessel per day or,
alternatively, the Company may purchase the vessels at their then fair market
values. Total lease expense under these leases from affiliate totaled
$3,600,000, $3,600,000 and $5,900,000 in 1994, 1995 and 1996.
    
 
     While the vessels were undergoing renovations, the Company leased barges
from a third party. In recognition of the $1,160,000 of additional barge rent
and $509,000 of other transitional expenses incurred in 1996 during the
renovation period, the affiliate agreed to reduce the charter rental due from
the Company by approximately $1,669,000.
 
     Guarantee Agreement.  The Company is the guarantor on an affiliated
company's construction loan for $26.5 million, and has pledged all assets to
secure this agreement. The loan is also collateralized by a mortgage on the
vessels and a lien on the related ramp structures which are owned by the
affiliate and leased to the Company.
 
   
6. CAPITAL LEASE OBLIGATIONS
    
 
   
     Future minimum lease payments under capital leases as of December 31, 1996
are as follows:
    
 
<TABLE>
<CAPTION>
YEAR ENDING DECEMBER 31:
- ------------------------
<S>                                                           <C>
1997........................................................  $ 55,727
1998........................................................    50,400
1999........................................................    50,400
2000........................................................    50,400
2001........................................................    45,378
                                                              --------
Total minimum lease payments................................   252,305
Interest portion............................................   (52,664)
                                                              --------
Present value of minimum lease payments.....................   199,641
Less current portion........................................   (38,197)
                                                              --------
                                                              $161,444
                                                              ========
</TABLE>
 
                                      F-10
<PAGE>   64
 
                              TRAILER BRIDGE, INC.
 
                  NOTES TO FINANCIAL STATEMENTS -- (CONTINUED)
 
7. LONG-TERM DEBT
 
     Following is a summary of long-term debt:
 
<TABLE>
<CAPTION>
                                                      DECEMBER 31,
                                                 -----------------------
                                                    1995         1996      MARCH 31,
                                                 ----------   ----------   ----------
<S>                                              <C>          <C>          <C>
Notes payable to finance company totaling
  $4,957,569 maturing from June to October
  2001; payable in 60 monthly installments of
  principal and interest; interest at fixed
  rates ranging from 8.867% to 9.290%;
  collateralized by trailers with a carrying
  value of $4,763,490 at December 31, 1996.....               $4,626,830   $4,420,979
Note payable to bank totaling $1,680,000
  maturing October 2006; payable in 120 monthly
  installments of principal and interest;
  interest at fixed rate of 7.95%;
  collateralized by land, construction in
  progress and buildings and structures with a
  carrying value of $1,703,900 at December 31,
  1996.........................................                1,652,000    1,610,000
Notes payable to bank totaling $6,333,512,
  maturing November 1997 to July 1998; payable
  in 48 monthly installments of principal and
  interest; interest at variable or fixed rate
  selected by the Company (7.125% at December
  31, 1996); collateralized by tractors with a
  carrying value of $2,775,799 at December 31,
  1996.........................................  $3,225,131    1,641,754    1,175,482
Notes payable to finance company totaling
  $1,032,500 maturing June 2000; payable in 60
  monthly installments of principal and
  interest; interest at a rate of 3.5% above
  LIBOR (8.875% at December 31, 1996);
  collateralized by trailers with a carrying
  value of $917,386 at December 31, 1996.......     894,834      681,800      630,364
Notes payable to finance company totaling
  $3,068,796, maturing July to November 1997;
  payable in 48 monthly installments of
  principal and interest; interest at a rate of
  3.75% above LIBOR (9.125% at December 31,
  1996); collateralized by tractors with a
  carrying value of $772,975 at December 31,
  1996.........................................   1,090,330      322,424      106,127
</TABLE>
 
                                      F-11
<PAGE>   65
 
                              TRAILER BRIDGE, INC.
 
                  NOTES TO FINANCIAL STATEMENTS -- (CONTINUED)
 
   
<TABLE>
<CAPTION>
                                                      DECEMBER 31,
                                                 -----------------------
                                                    1995         1996      MARCH 31,
                                                 ----------   ----------   ----------
<S>                                              <C>          <C>          <C>
Unsecured notes payable due in 1997; interest
  at prime plus 1% (9.25% at December 31,
  1996); principal is payable in semiannual
  installments.................................  $  304,000   $  101,333   $  101,333
Borrowings under $7.1 million line of credit
  maturing April 1, 2000; payable in 35 monthly
  installments of principal and interest plus a
  final payment of $340,205 plus interest;
  interest on outstanding borrowings at fixed
  rate of 7.98%; collateralized by tractors
  with a carrying value of $1,446,646 at March
  31, 1997 (unaudited).........................                             1,134,018
                                                 ----------   ----------   ----------
                                                  5,514,295    9,026,141    9,178,303
Less current portion...........................  (2,677,870)  (3,117,069)  (2,865,326)
                                                 ----------   ----------   ----------
                                                 $2,836,425   $5,909,072   $6,312,977
                                                 ==========   ==========   ==========
</TABLE>
    
 
     In March 1997, the Company obtained a $7.1 million line of credit from a
financial institution. At the election of the Company, interest on each
borrowing under the line of credit will accrue at (a) a variable interest rate
of the financial institution's Base Rate, (b) a variable interest rate of 1.40%
above the financial institution's Eurodollar Rate or (c) a fixed interest rate
of 1.40% above the financial institution's three year cost of funds. The line
will be used to purchase tractors which will be used as collateral.
 
     All long-term debt agreements at 1995 and 1996 are guaranteed by an
affiliated company. The notes include financial covenants that require that the
Company and affiliate, on a combined basis, maintain certain financial ratios
which are calculated as of the end of each fiscal quarter. As of December 31,
1996, the Company and affiliate were in compliance with such covenants.
 
     Following are maturities of long-term debt for each of the next five years:
 
<TABLE>
<CAPTION>
YEAR ENDING DECEMBER 31:
- ------------------------
<S>                                                           <C>
1997........................................................  $3,117,069
1998........................................................   1,465,021
1999........................................................   1,396,740
2000........................................................   1,375,147
2001........................................................     860,164
Thereafter..................................................     812,000
                                                              ----------
                                                              $9,026,141
                                                              ==========
</TABLE>
 
                                      F-12
<PAGE>   66
 
                              TRAILER BRIDGE, INC.
 
                  NOTES TO FINANCIAL STATEMENTS -- (CONTINUED)
 
8. OPERATING LEASES
 
     The Company has various operating lease agreements, principally for its
office facilities, terminals and equipment. Certain of the leases contain
provisions calling for additional contingent rentals based on volume of
transportation activity.
 
     Future minimum rental payments required under operating leases that have
initial or remaining noncancellable lease terms in excess of one year as of
December 31, 1996 are as follows:
 
<TABLE>
<CAPTION>
YEAR ENDING DECEMBER 31:
- ------------------------
<S>                                                           <C>
1997........................................................  $16,095,651
1998........................................................    8,070,107
1999........................................................    3,051,030
2000........................................................    1,823,277
2001........................................................    1,789,768
Thereafter..................................................    5,202,719
                                                              -----------
Total minimum payments required.............................  $36,032,552
                                                              ===========
</TABLE>
 
     Lease expense for all operating leases, including leases with terms of less
than one year, was $10,330,913, $12,683,332 and $14,806,980 for 1994, 1995 and
1996.
 
9. PROFIT SHARING/401(K) PLAN
 
     The Company has a profit sharing/401(k) Plan which covers substantially all
employees. Participants are allowed to make contributions of up to 15% of their
compensation not to exceed certain limits. The Company makes matching
contributions to the Plan at a rate not in excess of 3.0% of compensation. The
Company contributed approximately $137,640, $60,546 and $142,994 to the Plan
during 1994, 1995 and 1996. The Company made an optional contribution of $32,700
in December 1996.
 
10. COMMITMENT
 
     At December 31, 1996, the Company is obligated under construction
agreements totaling approximately $1.7 million.
 
11. RECAPITALIZATION
 
   
     In July 1997, the Company's Board of Directors and stockholders authorized
the following which will become effective in connection with the Company's
initial public offering: (i) a 15,700-for-1 stock split, (ii) an increase in the
authorized number of common shares from 2,000 to 20,000,000, (iii) a change in
the par value of common stock from $1.00 to $.01 and (iv) 1,000,000 shares of
preferred stock with a par value of $.01 per share. Stockholders' equity has
been restated to give retroactive recognition to the stock split and change in
par value in prior periods. In addition, all references in the financial
statements to the number of shares and per share amounts have been restated.
    
 
                                      F-13
<PAGE>   67
 
                              TRAILER BRIDGE, INC.
 
                  NOTES TO FINANCIAL STATEMENTS -- (CONTINUED)
 
   
12. SUBSEQUENT EVENTS (UNAUDITED)
    
 
     In January 1997, the Company entered into an agreement to purchase 100
tractors at an aggregate cost of approximately $7.2 million.
 
   
     In March 1997, the Company entered into an agreement for the construction
of two vessels, known as Triplestack Box Carriers(TM), for a total cost of
approximately $12 million. The Company plans to finance approximately $10.5
million of the acquisition cost with the assistance of the sale of bonds with a
Title XI guaranty commitment issued by the U.S. Maritime Administration. The
Title XI bonds sold in June 1997 call for even semi-annual principal payments
over a 25 year term. In addition, the Company has contracted for the
construction of 53' containers and chassis units with an aggregate cost of
approximately $13 million.
    
 
   
     In July 1997, the Company's Board of Directors and stockholders authorized
the establishment of an Incentive Stock Plan with a maximum of 785,000 shares
issuable under the Plan and the grant of options for 471,000 shares under the
Plan subject to consummation of the Company's initial public offering. These
options have an exercise price equal to the initial public offering price and
vest equally over a period of five years.
    
 
   
     In June 1997, the Company entered into amendments to its leases of two
roll-on/roll-off barge vessels and ramp system. The amendment reduces the total
payments under the lease from $21,000 to $20,100 per day effective with this
offering.
    
 
   
     On May 21, 1997, the majority stockholder of the Company granted to the
Company's Chairman and Chief Executive Officer, an option to purchase up to
942,000 shares of common stock (adjusted for the 15,700-for-1 stock split) owned
by him at $.95 per share or an aggregate price of $891,330 for all shares. These
options are immediately exercisable and have a term of 10 years. In connection
with this option, the Company expects to record a nonrecurring, noncash charge
for compensation expense and a credit to paid-in capital of approximately $10.4
million in the second quarter of 1997, representing the difference between the
exercise price and an assumed initial public offering price of the common stock
of $12.00 per share. This option does not involve the issuance of additional
shares of common stock by the Company and therefore, any subsequent purchase of
shares under the option will not have a dilutive effect on the Company's book
value or earnings per share amounts.
    
 
     The Company is in the process of an initial public offering of its shares
of common stock.
 
                                      F-14
<PAGE>   68
 
             ======================================================
 
  NO PERSON HAS BEEN AUTHORIZED IN CONNECTION WITH THE OFFERING MADE HEREBY TO
GIVE ANY INFORMATION OR TO MAKE ANY REPRESENTATION NOT CONTAINED IN THIS
PROSPECTUS AND, IF GIVEN OR MADE, SUCH INFORMATION OR REPRESENTATION MUST NOT BE
RELIED UPON AS HAVING BEEN AUTHORIZED BY THE COMPANY OR ANY UNDERWRITERS. THIS
PROSPECTUS DOES NOT CONSTITUTE AN OFFER TO SELL OR A SOLICITATION OF AN OFFER TO
BUY ANY OF THE SECURITIES OFFERED HEREBY TO ANY PERSON OR BY ANYONE IN ANY
JURISDICTION IN WHICH IT IS UNLAWFUL TO MAKE SUCH OFFER OR SOLICITATION. NEITHER
THE DELIVERY OF THIS PROSPECTUS NOR ANY SALE MADE HEREUNDER SHALL, UNDER ANY
CIRCUMSTANCES, CREATE ANY IMPLICATION THAT THE INFORMATION CONTAINED HEREIN IS
CORRECT AS OF ANY DATE SUBSEQUENT TO THE DATE HEREOF.
 
                               ------------------
 
                               TABLE OF CONTENTS
 
   
<TABLE>
<CAPTION>
                                        PAGE
                                        ----
<S>                                     <C>
Prospectus Summary....................    3
Risk Factors..........................    8
S Corporation Status..................   14
Use of Proceeds.......................   14
Dividend Policy.......................   14
Capitalization........................   15
Dilution..............................   16
Selected Financial and Operating
  Data................................   17
Management's Discussion and Analysis
  of Financial Condition and Results
  of Operations.......................   19
Industry Overview.....................   27
Business..............................   28
Management............................   38
Certain Transactions..................   42
Principal Stockholders................   43
Description of Capital Stock..........   44
Shares Eligible for Future Sale.......   49
Underwriting..........................   50
Legal Matters.........................   51
Experts...............................   51
Additional Information................   52
</TABLE>
    
 
                               ------------------
  UNTIL                , 1997 (25 DAYS AFTER THE DATE OF THIS PROSPECTUS), ALL
DEALERS EFFECTING TRANSACTIONS IN THE COMMON STOCK OFFERED HEREBY, WHETHER OR
NOT PARTICIPATING IN THIS DISTRIBUTION, MAY BE REQUIRED TO DELIVER A PROSPECTUS.
THIS IS IN ADDITION TO THE OBLIGATION OF DEALERS TO DELIVER A PROSPECTUS WHEN
ACTING AS UNDERWRITERS AND WITH RESPECT TO THEIR UNSOLD ALLOTMENTS OR
SUBSCRIPTIONS.
             ======================================================
             ======================================================
 
   
                                2,700,000 SHARES
    
 
                             [Trailer Bridge Logo]
 
   
                              TRAILER BRIDGE, INC.
    
                                  COMMON STOCK
                            -----------------------
                                   PROSPECTUS
                            -----------------------
                               ALEX. BROWN & SONS
                                  INCORPORATED
 
                                            , 1997
             ======================================================
<PAGE>   69
 
                                    PART II
 
                     INFORMATION NOT REQUIRED IN PROSPECTUS
 
ITEM 13.  OTHER EXPENSES OF INSURANCE AND DISTRIBUTION.
 
   
<TABLE>
<S>                                                           <C>
Securities and Exchange Commission filing fee...............  $ 12,232
NASD filing fee.............................................     4,537
Nasdaq listing fee..........................................    42,500*
Transfer agent expenses and fees............................     2,500*
Printing and engraving......................................    64,000*
Accountants' fees and expenses..............................   100,000*
Legal fees and expenses.....................................    95,000*
Miscellaneous...............................................    11,231*
                                                              --------
          Total.............................................  $332,000*
                                                              ========
</TABLE>
    
 
- ---------------
 
* Other than the SEC filing fee and NASD filing fee, all fees and expenses are
  estimated.
 
   
ITEM 14.  INDEMNIFICATION OF DIRECTORS AND OFFICERS.
    
 
     The Delaware General Corporation Law (the "Delaware Act") permits a
Delaware corporation to indemnify a present or former director or officer of the
corporation (and certain other persons serving at the request of the corporation
in related capacities) for liabilities, including legal expenses, arising by
reason of service in such capacity if such person shall have acted in good faith
and in a manner he reasonably believed to be in or not opposed to the best
interests of the corporation, and in any criminal proceeding if such person had
no reasonable cause to believe his conduct was unlawful. However, in the case of
actions brought by or in the right of the corporation, no indemnification may be
made with respect to any matter as to which such director or officer shall have
been adjudged liable, except in certain limited circumstances.
 
     The Company's Amended and Restated Certificate of Incorporation and Amended
and Restated Bylaws provide that the Company may indemnify directors and
officers to the fullest extent now or hereafter permitted by the Delaware Act.
In addition, the Company intends to enter into Indemnification Agreements with
its directors and executive officers in which the Registrant will agree to
indemnify such persons to the fullest extent now or hereafter permitted by the
Delaware Act.
 
     The indemnification provided by the Delaware General Corporation Law and
the Company's Amended and Restated Bylaws is not exclusive of any other rights
to which a director or officer may be entitled. The general effect of the
foregoing provisions may be to reduce the circumstances in which an officer or
director may be required to bear the economic burden of the foregoing
liabilities and expense.
 
     The Company may obtain a liability insurance policy for its directors and
officers as permitted by the Delaware Act which may extend to, among other
things, liability arising under the Securities Act of 1933, as amended (the
"Securities Act").
 
ITEM 15.  RECENT SALES OF UNREGISTERED SECURITIES.
 
     The Company was incorporated under the laws of the State of Delaware
effective April 1, 1991. The Company has not made any sales of securities during
the last three years.
 
                                      II-1
<PAGE>   70
 
ITEM 16.  EXHIBITS AND FINANCIAL STATEMENT SCHEDULES.
 
     (a) Exhibits.
 
   
<TABLE>
<S>       <C>  <S>
    1.1    --  Form of Underwriting Agreement
    3.1    --  Form of Amended and Restated Certificate of Incorporation of
               the Registrant
    3.2    --  Form of Amended and Restated Bylaws of the Registrant
    4.1    --  See Exhibits 3A and 3B for provisions of the Certificate of
               Incorporation and Bylaws of the Registrant defining the
               rights of holders of the Registrant's Common Stock
    5.1    --  Opinion of Foley & Lardner as to the legality of the
               securities to be issued
 **10.1    --  Form of Indemnification Agreement with Directors and
               Executive Officers
  *10.2    --  Bareboat Charter Party dated February 1992
  *10.2.1  --  Amendment to Bareboat Charter Party dated December 31, 1994
  *10.2.2  --  Second Amendment to Bareboat Charter Party dated October
               1995
  *10.2.3  --  Third Amendment to Bareboat Charter Party dated March 1,
               1997
 **10.2.4  --  Form of Fourth Amendment to Bareboat Charter Party
  *10.3    --  Promissory Note dated January 1, 1997 payable to
               Kadampanattu Corp. in the principal amount of $4,569,131
  *10.4    --  Construction and Term Loan Agreement dated as of October 13,
               1995 between the Registrant, Kadampanattu Corp. and The
               First National Bank of Boston, as Agent
  *10.4.1  --  First Amendment to Construction and Term Loan Agreement
               dated as of May 9, 1996
  *10.4.2  --  Second Amendment to Construction and Term Loan Agreement
               dated as of July 10, 1996
   10.4.3  --  Third Amendment to Construction and Term Loan Agreement and
               Consent and Limited Waiver dated as of January 1, 1997
  *10.5    --  Chattel Mortgage Line of Credit Agreement dated as of
               February 28, 1997
  *10.6    --  Vessel Construction Contract dated as of December 30, 1996
               between Coastal Ship, Inc. and Halter Marine, Inc.
  *10.6.1  --  Assignment of Vessel Construction Contract dated March 24,
               1997 between Coastal Ship, Inc. and the Registrant
  *10.6.2  --  Amendment No. 1 to Vessel Construction Contract dated as of
               April 1997
  *10.7    --  Real Estate Promissory Note dated April 18, 1996 between the
               Registrant and First Union National Bank of Florida
   10.8    --  Commitment to Guarantee Obligations
   10.8.1  --  Trust Indenture
   10.8.2  --  United States Government Ship Financing Bond, 1997 Series in
               the amount of $10,515,000
 **10.9    --  Agreement and Lease dated as of August 1, 1991 between the
               Registrant and the Jacksonville Port Authority
 **10.9.1  --  Amendment #5 to Exhibit B, Schedule of Fees and Charges
 **10.10   --  Time Charter dated January 31, 1994 between the Registrant
               and Tidewater Marine, Inc. Towing Division
 **10.11   --  Incentive Stock Plan
 **10.11.1  -- Form of Stock Option Award Agreement
 **23.1    --  Consent of Deloitte & Touche LLP
</TABLE>
    
 
                                      II-2
<PAGE>   71
   
   23.2    --  Consent of Foley & Lardner (included in Opinion filed as
               Exhibit 5)
  *24.1    --  Powers of Attorney (included on signature page of the S-1
               Registration Statement)
  *27.1    --  Financial Data Schedule
 
    
- ---------------
 
 * Filed May 30, 1997.
   
** To be filed by amendment.
    
 
     (b) Financial Statement Schedules.
 
   
     Report of Independent Auditors
    
 
   
     Schedule II -- Valuation and Qualifying Accounts.
    
 
     All other financial statement schedules have been omitted either because
they are not applicable or because the information that would be included in
such schedules is included elsewhere in this Registration Statement.
 
ITEM 17.  UNDERTAKINGS.
 
     The undersigned Registrant hereby undertakes to provide to the underwriters
at the closing specified in the underwriting agreement certificates in such
denominations and registered in such names as required by the underwriters to
permit prompt delivery to each purchaser.
 
     Insofar as indemnification for liabilities arising under the Securities Act
of 1933 may be permitted to directors, officers and controlling persons of the
Registrant pursuant to the foregoing provisions, or otherwise, the Registrant
has been advised that in the opinion of the Securities and Exchange Commission
such indemnification is against public policy as expressed in the Act and is,
therefore, unenforceable. In the event that a claim for indemnification against
such liabilities (other than the payment by the Registrant of expenses incurred
or paid by a director, officer or controlling person of the Registrant in the
successful defense of any action, suit or proceeding) is asserted by such
director, officer or controlling person in connection with the securities being
registered, the Registrant will, unless in the opinion of its counsel the matter
has been settled by controlling precedent, submit to a court of appropriate
jurisdiction the question whether such indemnification by it is against public
policy as expressed in the Act and will be governed by the final adjudication of
such issue.
 
     The undersigned Registrant hereby undertakes that:
 
          (1) For purposes of determining any liability under the Securities Act
     of 1933, the information omitted from the form of prospectus filed as part
     of this registration statement in reliance upon Rule 430A and contained in
     a form of prospectus filed by the Registrant pursuant to Rule 424(b)(1) or
     (4) or 497(h) under the Securities Act shall be deemed to be part of this
     registration statement as of the time it was declared effective.
 
          (2) For the purpose of determining any liability under the Securities
     Act of 1933, each post-effective amendment that contains a form of
     prospectus shall be deemed a new registration statement relating to the
     securities offered therein, and the offering of such securities at that
     time shall be deemed to be the initial bona fide offering thereof.
 
                                      II-3
<PAGE>   72
 
                                   SIGNATURES
 
   
     Pursuant to the requirements of the Securities Act of 1933, the Registrant
has duly caused this amended Registration Statement to be signed on its behalf
by the undersigned, thereunto duly authorized, in the City of New York, and
State of New York, on this 30th day of June 1997.
    
 
                                          TRAILER BRIDGE, INC.
 
                                          By:      /s/ JOHN D. MCCOWN
                                            ------------------------------------
                                            John D. McCown
                                            Chairman of the Board and Chief
                                              Executive Officer
 
     Pursuant to the requirements of the Securities Act of 1933, this
Registration Statement has been signed below by the following persons in the
capacities and on the dates indicated.
 
   
<TABLE>
<CAPTION>
                      SIGNATURE                                     TITLE                    DATE
                      ---------                                     -----                    ----
<S>                                                    <C>                               <C>
                 /s/ JOHN D. MCCOWN                    Chairman of the Board and Chief
- -----------------------------------------------------  Executive Officer and Director
                   John D. McCown                      (Principal Executive Officer)     June 30, 1997
 
                 /s/ MARK A. TANNER                    Vice President -- Administration
- -----------------------------------------------------  and Chief Financial Officer
                   Mark A. Tanner                      (Principal Financial and          June 30, 1997
                                                       Accounting Officer)
 
                /s/ MALCOM P. MCLEAN                   Director
- -----------------------------------------------------
                  Malcom P. McLean                                                       June 30, 1997
</TABLE>
    
 
                                      II-4
<PAGE>   73
 
                                 EXHIBIT INDEX
 
   
<TABLE>
<CAPTION>
                                                                             SEQUENTIALLY
   EXHIBIT                                                                     NUMBERED
   NUMBER                        DESCRIPTION OF EXHIBITS                         PAGE
   -------                       -----------------------                     ------------
<C>       <C>  <S>                                                           <C>
    1.1    --  Form of Underwriting Agreement
    3.1    --  Form of Amended and Restated Certificate of Incorporation of
               the Registrant
    3.2    --  Form of Amended and Restated Bylaws of the Registrant
    4.1    --  See Exhibits 3A and 3B for provisions of the Certificate of
               Incorporation and Bylaws of the Registrant defining the
               rights of holders of the Registrant's Common Stock
    5.1    --  Opinion of Foley & Lardner as to the legality of the
               securities to be issued
 **10.1    --  Form of Indemnification Agreement with Directors and
               Executive Officers
  *10.2    --  Bareboat Charter Party dated February 1992
  *10.2.1  --  Amendment to Bareboat Charter Party dated December 31, 1994
  *10.2.2  --  Second Amendment to Bareboat Charter Party dated October
               1995
  *10.2.3  --  Third Amendment to Bareboat Charter Party dated March 1,
               1997
   10.2.4  --  Form of Fourth Amendment to Bareboat Charter Party
  *10.3    --  Promissory Note dated January 1, 1997 payable to
               Kadampanattu Corp. in the principal amount of $4,569,131
  *10.4    --  Construction and Term Loan Agreement dated as of October 13,
               1995 between the Registrant, Kadampanattu Corp. and The
               First National Bank of Boston, as Agent
  *10.4.1  --  First Amendment to Construction and Term Loan Agreement
               dated as of May 9, 1996
  *10.4.2  --  Second Amendment to Construction and Term Loan Agreement
               dated as of July 10, 1996
   10.4.3  --  Third Amendment to Construction and Term Loan Agreement and
               Consent and Limited Waiver dated as of January 1, 1997
  *10.5    --  Chattel Mortgage Line of Credit Agreement dated as of
               February 28, 1997
  *10.6    --  Vessel Construction Contract dated as of December 30, 1996
               between Coastal Ship, Inc. and Halter Marine, Inc.
  *10.6.1  --  Assignment of Vessel Construction Contract dated March 24,
               1997 between Coastal Ship, Inc. and the Registrant
  *10.6.2  --  Amendment No. 1 to Vessel Construction Contract dated as of
               April 1997
  *10.7    --  Real Estate Promissory Note dated April 18, 1996 between the
               Registrant and First Union National Bank of Florida
   10.8    --  Commitment to Guarantee Obligations
   10.8.1  --  Trust Indenture
   10.8.2  --  United States Government Ship Financing Bond, 1997 Series in
               the amount of $10,515,000

</TABLE>
    
 
                                       S-1
<PAGE>   74
   
<TABLE>
<CAPTION>
                                                                             SEQUENTIALLY
   EXHIBIT                                                                     NUMBERED
   NUMBER                        DESCRIPTION OF EXHIBITS                         PAGE
   -------                       -----------------------                     ------------
<C>       <C>  <S>                                                           <C>
 **10.9    --  Agreement and Lease dated as of August 1, 1991 between the
               Registrant and the Jacksonville Port Authority
 **10.9.1  --  Amendment #5 to Exhibit B, Schedule of Fees and Charges
 **10.10   --  Time Charter dated January 31, 1994 between the Registrant
               and Tidewater Marine, Inc. Towing Division
 **10.11   --  Incentive Stock Plan
 **10.11.1  -- Form of Stock Option Award Agreement
 **23.1    --  Consent of Deloitte & Touche LLP
   23.2    --  Consent of Foley & Lardner (included in Opinion filed as
               Exhibit 5)
  *24.1    --  Powers of Attorney (included on signature page of the S-1
               Registration Statement)
  *27.1    --  Financial Data Schedule
</TABLE>
    
 
- ---------------
 
 * Filed May 30, 1997.
   
** To be filed by amendment.
    
 
                                       S-2

<PAGE>   1
                                                                    EXHIBIT 1.1

                               [2,700,000] SHARES

                              TRAILER BRIDGE, INC.

                                  COMMON STOCK

                                ($.01 PAR VALUE)


                             UNDERWRITING AGREEMENT


                                                           _______________, 1997



Alex. Brown & Sons Incorporated
As Representative of the
     Several Underwriters
c/o  Alex. Brown & Sons Incorporated
135 East Baltimore Street
Baltimore, Maryland 21202

Gentlemen:

     Trailer Bridge, Inc., a Delaware corporation (the "Company"), proposes to
sell to the several underwriters (the "Underwriters") named in Schedule I
hereto for whom you are acting as representative (the "Representative") an
aggregate of [2,700,000] shares of the Company's Common Stock, $.01 par value
(the "Firm Shares").  The respective amounts of the Firm Shares to be so
purchased by the several Underwriters are set forth opposite their names in
Schedule I hereto. The Company also proposes to sell at the Underwriters'
option an aggregate of up to [405,000] additional shares of the Company's
Common Stock (the "Option Shares") as set forth below.

     As the Representative, you have advised the Company (a) that you are
authorized to enter into this Agreement on behalf of the several Underwriters,
and (b) that the several Underwriters are willing, acting severally and not
jointly, to purchase the numbers of Firm Shares set forth opposite their
respective names in Schedule I, plus their pro rata portion of the Option
Shares if you elect to exercise the over-allotment option in whole or in part
for the accounts of the several Underwriters.  The Firm Shares and the Option
Shares (to the extent the aforementioned option is exercised) are herein
collectively called the "Shares."

     In consideration of the mutual agreements contained herein and of the
interests of the parties in the transactions contemplated hereby, the parties
hereto agree as follows:
                                                                          

<PAGE>   2



      1.   REPRESENTATIONS AND WARRANTIES OF THE COMPANY.

           The Company represents and warrants to each of the Underwriters as
      follows:

           (a) A registration statement on Form S-1 (File No. 333-28221) with
      respect to the Shares has been carefully prepared by the Company in
      conformity with the requirements of the Securities Act of 1933, as
      amended (the "Act"), and the Rules and Regulations (the "Rules and
      Regulations") of the Securities and Exchange Commission (the
      "Commission") thereunder and has been filed with the Commission.  Copies
      of such registration statement, including any amendments thereto, the
      preliminary prospectuses (meeting the requirements of the Rules and
      Regulations) contained therein and the exhibits, financial statements and
      schedules, as finally amended and revised, have heretofore been delivered
      by the Company to you.  Such registration statement, together with any
      registration statement filed by the Company pursuant to Rule 462 (b) of
      the Act, herein referred to as the "Registration Statement," which shall
      be deemed to include all information omitted therefrom in reliance upon
      Rule 430A and contained in the Prospectus referred to below, has become
      effective under the Act and no post-effective amendment to the
      Registration Statement has been filed as of the date of this Agreement.
      "Prospectus" means (a) the  form of prospectus first filed with the
      Commission pursuant to Rule 424(b) or (b) the last preliminary prospectus
      included in the Registration Statement filed prior to the time it becomes
      effective or filed pursuant to Rule 424(a) under the Act that is
      delivered by the Company to the Underwriters for delivery to purchasers
      of the Shares, together with the term sheet or abbreviated term sheet
      filed with the Commission pursuant to Rule 424(b)(7) under the Act.  Each
      preliminary prospectus included in the Registration Statement prior to
      the time it becomes effective is herein referred to as a "Preliminary
      Prospectus." Any reference herein to the Registration Statement, any
      Preliminary Prospectus or to the Prospectus shall be deemed to refer to
      and include any documents incorporated by reference therein, and, in the
      case of any reference herein to any Prospectus, also shall be deemed to
      include any documents incorporated by reference therein, and any
      supplements or amendments thereto, filed with the Commission after the
      date of filing of the Prospectus under Rules 424(b) or 430A, and prior to
      the termination of the offering of the Shares by the Underwriters.

           (b) The Company has been duly organized and is validly existing as a
      corporation in good standing under the laws of the State of Delaware,
      with corporate power and authority to own or lease its properties and 
      conduct its business as described in the Registration Statement.  Each of
      the subsidiaries of the Company as listed in Exhibit 21 to Item 16(a) of 
      the Registration Statement (collectively, the "Subsidiaries") has been 
      duly organized and is validly existing as a corporation in good standing 
      under the laws of the jurisdiction of its incorporation, with corporate 
      power and authority to own or lease its properties and conduct its 
      business as described in the Registration Statement. The Subsidiaries are
      the only subsidiaries, direct or indirect, of the Company.  The Company 
      and each of the Subsidiaries are duly qualified to transact business in 
      all jurisdictions in which the conduct of their business requires such   
      qualification.  The outstanding shares of capital stock of each of the   
      Subsidiaries have been duly authorized and validly issued, are 
                                                                               
                                      2
                                                                               
<PAGE>   3
                                                                               
                                                                              
      fully paid assessable and are owned by the Company or another Subsidiary
      free and clear of all liens, encumbrances and equities and claims; and no
      options, warrants or other rights to purchase, agreements or other
      obligations to issue or other rights to convert any obligations into
      shares of capital stock or ownership interests in the Subsidiaries are
      outstanding.

           (c) The outstanding shares of Common Stock of the Company have been
      duly authorized and validly issued and are fully paid and non-assessable;
      the Shares to be issued and sold by the Company have been duly authorized
      and when issued and paid for as contemplated herein will be validly
      issued, fully paid and non-assessable; and no preemptive rights of
      stockholders exist with respect to any of the Shares or the issue and
      sale thereof.  Neither the filing of the Registration Statement nor the
      offering or sale of the Shares as contemplated by this Agreement gives
      rise to any rights, other than those which have been waived or satisfied,
      for or relating to the registration of any shares of Common Stock.

           (d) The information set forth under the caption "Capitalization" in
      the Prospectus is true and correct.  All of the Shares conform to the
      description thereof contained in the Registration Statement.  The  form
      of certificates for the Shares conforms to the corporate law of the
      jurisdiction of the Company's incorporation.

           (e) The Commission has not issued an order preventing or suspending
      the use of any Prospectus relating to the proposed offering of the Shares
      nor instituted proceedings for that purpose.   The Registration Statement
      contains, and the Prospectus and any amendments or supplements thereto
      will contain, all statements which are required to be stated therein by,
      and will conform, to the requirements of the Act and the Rules and
      Regulations.  The Registration Statement and any amendment thereto do not
      contain, and will not contain, any untrue statement of a material fact
      and do not omit, and will not omit, to state any material fact
      required to be stated therein or necessary to make the statements therein
      not misleading.  The Prospectus and any amendments and supplements
      thereto do not contain, and will not contain, any untrue statement of
      material fact; and do not omit, and will not omit, to state any material
      fact required to be stated therein or necessary to make the statements
      therein, in the light of the circumstances under which they were made,
      not misleading; provided, however, that the Company makes no
      representations or warranties as to information contained in or omitted
      from the Registration Statement or the Prospectus, or any such amendment
      or supplement, in reliance upon, and in conformity with, written
      information furnished to the Company by or on behalf of any Underwriter
      through the Representative, specifically for use in the preparation
      thereof.

           (f) The consolidated financial statements of the Company and the
      Subsidiaries, together with related notes and schedules as set forth in
      the Registration Statement, present fairly the financial position and the
      results of operations and cash flows of the Company and the consolidated
      Subsidiaries, at the indicated dates and for the indicated periods.  Such
      financial statements and related schedules have been prepared in
      accordance with generally accepted principles of accounting, consistently
      applied 

                                      3
<PAGE>   4

      throughout the periods involved, except as disclosed herein, and
      all adjustments necessary for a fair presentation of results for such
      periods have been made.  The summary financial and statistical data
      included in the Registration Statement, including the data set forth in
      the Prospectus under the captions "Prospectus Summary," "Capitalization,"
      "Dilution" and "Selected Financial Data," presents fairly the
      information shown therein and such data has been compiled on a basis
      consistent with the financial statements presented therein and the books
      and records of the company.  The pro forma financial statements and other
      pro forma financial information included in the Registration Statement
      and the Prospectus present fairly the information shown therein, have
      been prepared in accordance with the Commission's rules and guidelines
      with respect to pro forma financial statements, have been properly
      compiled on the pro forma bases described therein, and, in the opinion of
      the Company, the assumptions used in the preparation thereof are
      reasonable and the adjustments used therein are appropriate to give
      effect to the transactions or circumstances referred to therein.

           (g) Deloitte & Touche LLP, who have certified certain of the
      financial statements filed with the Commission as part of the
      Registration Statement, are independent public accountants as required by
      the Act and the Rules and Regulations.

           (h) There is no action, suit, claim or proceeding pending or, to the
      knowledge of the Company, threatened against the Company or any of the
      Subsidiaries before any court or administrative agency or otherwise which
      if determined adversely to the Company or any of its Subsidiaries might
      result in any material adverse change in the earnings, business,
      management, properties, assets, rights, operations, condition (financial
      or otherwise) or prospects of the Company and of the Subsidiaries taken
      as a whole or to prevent the consummation of the transactions
      contemplated hereby, except as set forth in the Registration Statement.
      No labor disturbance by the employees of the Company or any of its
      subsidiaries exists or is imminent which might be expected to affect
      adversely such condition, properties, business, results of operations or
      prospects.  Neither the Company nor any of its Subsidiaries is a party
      or, to the Company's knowledge, subject to the provisions of any material
      injunction, judgment, decree or order of any court, regulatory body,
      administrative agency or other governmental body.

           (i) The Company and the Subsidiaries have good and marketable title
      to all of the properties and assets reflected in the financial statements
      (or as described in the Registration Statement) hereinabove described,
      subject to no lien, mortgage, pledge, charge or encumbrance of any kind
      except those reflected in such financial statements (or as described in
      the Registration Statement) or which are not material in amount.  The
      Company and the Subsidiaries occupy their leased properties under valid
      and binding leases conforming in all material respects to the description
      thereof set forth in the Registration Statement.

           (j) The Company and the Subsidiaries have filed all Federal, State,
      local and foreign income tax returns which have been required to be filed
      and have paid all taxes indicated by said returns and all assessments
      received by them or any of them to the 


                                      4
<PAGE>   5

      extent that such taxes have become due and are not being contested in 
      good faith.  All tax liabilities have been adequately provided for in the
      financial statements of the Company.

           (k) Since the respective dates as of which information is given in
      the Registration Statement, as it may be amended or supplemented, there
      has not been any material adverse change or any development involving a
      prospective material adverse change in or affecting the earnings,
      business,  management, properties, assets, rights, operations, condition
      (financial or otherwise), or prospects of the Company and its
      Subsidiaries taken as a whole, whether or not occurring in the ordinary
      course of business, and there has not been any material transaction
      entered into or any material transaction that is probable of being
      entered into by the Company or the Subsidiaries, other than transactions
      in the ordinary course of business and changes and transactions described
      in the Registration Statement, as it may be amended or supplemented.  The
      Company and the Subsidiaries have no material contingent obligations
      which are not disclosed in the Company's financial statements which are
      included in the Registration Statement.

           (l) There are no contracts or other documents required to be
      described in the Registration Statement or to be filed as exhibits to the
      Registration Statement by the Act or by the Rules and Regulations which
      have not been described or filed as required.  The contracts so described
      in the Prospectus are in full force and effect on the date hereof; and
      neither the Company nor any of the Subsidiaries is or with the giving of
      notice or lapse of time or both, will be, in violation of or in default
      under  its Charter or By-Laws or under any agreement, lease, contract,
      indenture or other instrument or obligation to which it is a party or by
      which it, or any of its properties, is bound and which default is of
      material significance in respect of the condition, financial or otherwise
      of the Company and its Subsidiaries taken as a whole or the business,
      management, properties, assets, rights, operations, condition (financial
      or otherwise) or prospects of the Company and the Subsidiaries taken as a
      whole.  The execution and delivery of this Agreement and the consummation
      of the transactions herein contemplated and the fulfillment of the terms
      hereof will not conflict with or result in a breach of any of the terms
      or provisions of, or constitute a default under, any indenture, mortgage,
      deed of trust or other agreement or instrument to which the Company or
      any Subsidiary is a party, or of the Charter or by-laws of the Company or
      any order, rule or regulation applicable to the Company or any Subsidiary
      of any court or of any regulatory body or administrative agency or other
      governmental body having jurisdiction.

           (m) Each approval, consent, order, authorization, designation,
      declaration or filing by or with any regulatory, administrative or other
      governmental body necessary in connection with the execution and delivery
      by the Company of this Agreement and the consummation of the transactions
      herein contemplated (except such additional steps as may be required by
      the Commission, the National Association of Securities Dealers, Inc. (the
      "NASD") or such additional steps as may be necessary to qualify the
      Shares for public offering by the Underwriters under state securities or
      Blue Sky laws) has been obtained or made and is in full force and effect.


                                      5

<PAGE>   6

           (n) The Company and each of the Subsidiaries holds all material
      licenses, certificates and permits from governmental authorities which
      are necessary to the conduct of their businesses ("Permits") in the
      manner described in the Prospectus, including, without limitation, all
      Permits required under federal and state maritime, common carrier,
      environmental, labor, and insurance laws and regulations applicable to
      the Company and the Subsidiaries and their respective operations; the
      Company and each of the Subsidiaries has fulfilled and performed all its
      materials obligations with respect to such Permits and no event has
      occurred which allows, or after notice or lapse of time would allow,
      revocation or termination thereof or result in any other material
      impairment of the rights of the holder of any such Permit; and neither
      the Company nor any of the Subsidiaries has infringed any patents, patent
      rights, trade names, trademarks or copyrights, which infringement is 
      material to the business of the Company and the Subsidiaries taken as a 
      whole.  The Company knows of no material infringement by others of 
      patents, patent rights, trade names, trademarks or copyrights owned by or
      licensed to the Company.

           (o) Neither the Company, nor to the Company's best knowledge, any of
      its affiliates, has taken or may take, directly or indirectly, any action
      designed to cause or result in, or which has constituted or which might
      reasonably be expected to constitute, the stabilization or manipulation
      of the price of the shares of Common Stock to facilitate the sale or
      resale of the Shares.

           (p) Neither the Company nor any Subsidiary is an "investment
      company" within the meaning of such term under the Investment Company Act
      of 1940 and the rules and regulations of the Commission thereunder.

           (q) The Company maintains a system of internal accounting controls
      sufficient to provide reasonable assurances that (i) transactions are
      executed in accordance with management's general or specific
      authorization; (ii) transactions are recorded as necessary to permit
      preparation of financial statements in conformity with generally accepted
      accounting principles and to maintain accountability for assets; (iii)
      access to assets is permitted only in accordance with management's
      general or specific authorization; and (iv) the recorded accountability
      for assets is compared with existing assets at reasonable intervals and
      appropriate action is taken with respect to any differences.

           (r) The Company and each of its Subsidiaries carry, or are covered
      by, insurance in such amounts and covering such risks as is adequate for
      the conduct of their respective businesses and the value of their
      respective properties and as is customary for companies engaged in
      similar industries.

           (s) The Company is in compliance in all material respects with all
      presently applicable provisions of the Employee Retirement Income
      Security Act of 1974, as amended, including the regulations and published
      interpretations thereunder ("ERISA"); no "reportable event" (as defined
      in ERISA) has occurred with respect to any "pension plan" (as defined in
      ERISA) for which the Company would have any liability; the Company has
      not incurred and does not expect to incur liability under (i) Title IV of

                                      6
<PAGE>   7

      ERISA with respect to termination of, or withdrawal from, any "pension
      plan" or (ii) Sections 412 or 4971 of the Internal Revenue Code of 1986,
      as amended, including the regulations and published interpretations
      thereunder (the "Code"); and each "pension plan" for which the Company
      would have any liability that is intended to be qualified under Section
      401(a) of the Code is so qualified in all material respects and nothing 
      has occurred, whether by action or by failure to act, which would cause 
      the loss of such qualification.

           (t) The Company confirms as of the date hereof that it is in
      compliance with all provisions of Section 1 of Laws of Florida, Chapter
      92-198, An Act Relating to Disclosure of doing Business with Cuba, and
      the Company further agrees that if it commences engaging in business with
      the government of Cuba or with any person or affiliate located in Cuba
      after the date the Registration Statement becomes or has become effective
      with the Commission or with the Florida Department of Banking and
      Finance (the "Department"), whichever date is later, or if the
      information reported or incorporated by reference in the Prospectus, if
      any, concerning the Company's business with Cuba or with any person or
      affiliate located in Cuba changes in any material way, the Company will
      provide the Department notice of such business or change, as appropriate,
      in a form acceptable to the Department.

           (u) The Company has not been advised, and has no reason to believe,
      that either it or any of its Subsidiaries is not conducting its business
      in compliance with all applicable laws, rules and regulations of the
      jurisdictions in which it is conducting business, including, without
      limitation, all applicable local, state and federal maritime, common
      carrier and environmental laws and regulations, except where failure to
      be so in compliance would not materially adversely affect the condition
      (financial or otherwise), business, results of operations or prospects of
      the Company and its Subsidiaries.

           (v) The Company has not distributed, and will not distribute prior
      to completion of the distribution of the Shares, any offering materials
      in connection with the offering and sale of the Shares other than the
      Prospectus, the Registration Statement and the other materials permitted
      by the Act.

           (w) Neither the Company nor any of its Subsidiaries has at any time
      during the last five years (i) made any unlawful contribution to any
      candidate for foreign office, or failed to disclose fully any
      contribution in violation of law or (ii) made any payment to any federal
      or state governmental officer or official, or other person charged with
      similar public or quasi-public duties, other than payments required or
      permitted by the laws of the United States or any jurisdiction thereof.

           (x) The Shares have been duly approved for inclusion in the Nasdaq
      National Market under the symbol "TRBR" subject to notice of issuance of
      the Shares being sold by the Company, and upon consummation of the
      offering contemplated hereby the Company will be in compliance with
      the designation and maintenance criteria applicable to Nasdaq National
      Market issuers.           

                                      7
      
<PAGE>   8

           (y) Except as set forth in the Prospectus, there are no transactions
      with "affiliates" (as defined in Rule 405 promulgated under the Act) or
      any officer, director or security holder of the Company (whether or not
      an affiliate) which are required by the Act and the applicable rules and
      regulations thereunder to be disclosed in the Registration Statement.

           (z) The execution and delivery of, and the performance by the
      Company of its obligations under, this Agreement have been duly and
      validly authorized by the Company, and this Agreement has been duly
      executed and delivered by the Company and constitutes the valid and
      legally binding agreement of the Company, enforceable against the Company
      in accordance with its terms, except to the extent enforceability may be
      limited by bankruptcy, insolvency, reorganization, moratorium or other
      similar laws relating to creditors' rights generally or by general
      equitable principles, and except as rights to indemnity or contribution
      hereunder may be limited by applicable laws or public policy.

      2. PURCHASE, SALE AND DELIVERY OF THE FIRM SHARES.

           (a) On the basis of the representations, warranties and covenants
      herein contained, and subject to the conditions herein set forth, the
      Company agrees to sell to the Underwriters and each Underwriter agrees,
      severally and not jointly, to purchase, at a price of $_____ per share,
      the number of Firm Shares set forth opposite the name of each Underwriter
      in Schedule I hereof, subject to adjustments in accordance with Section 9
      hereof.

           (b) Payment for the Firm Shares to be sold hereunder is to be made
      in New York Clearing House funds by certified or bank cashier's checks
      drawn to the order of the Company against delivery of certificates
      therefor to the Representative for the several accounts of the
      Underwriters.  Such payment and delivery are to be made at the offices of
      Alex. Brown & Sons Incorporated, 135 East Baltimore Street, Baltimore,
      Maryland, at 10:00 a.m., Baltimore time, on the third business day after
      the date of this Agreement or at such other time and date not later than
      five business days thereafter as you and the Company shall agree upon,
      such time and date being herein referred to as the "Closing Date."  (As
      used herein, "business day" means a day on which the New York Stock
      Exchange is open for trading and on which banks in New York are open for
      business and are not permitted by law or executive order to be closed.)
      The certificates for the Firm Shares will be delivered in such
      denominations and in such registrations as the Representative requests in
      writing not later than the second full business day prior to the Closing 
      Date, and will be made available for inspection by the Representative at 
      least one business day prior to the Closing Date.

           (c) In addition, on the basis of the representations and warranties
      herein contained and subject to the terms and conditions herein set
      forth, the Company hereby grants an option to the several Underwriters to
      purchase the Option Shares at the price per share as set forth in the
      first paragraph of this Section 2.  The option granted hereby may be
      exercised in whole or in part by giving written notice (i) at any time
      before the Closing 

                                      8


<PAGE>   9

      Date and (ii) only once thereafter within 30 days after the date of this 
      Agreement, by you, as Representative of the several Underwriters, to
      the Company setting forth the number of Option Shares as to which the
      several Underwriters are exercising the option, the names and
      denominations in which the Option Shares are to be registered and the
      time and date at which such certificates are to be delivered.  The time
      and date at which certificates for Option Shares are to be delivered
      shall be determined by the Representative but shall not be earlier than
      three nor later than 10 full business days after the exercise of such
      option, nor in any event prior to the Closing Date (such time and date
      being herein referred to as the "Option Closing Date").  If the date of
      exercise of the option is three or more days before the Closing Date, the
      notice of exercise shall set the Closing Date as the Option Closing Date. 
      The number of Option Shares to be purchased by each Underwriter shall be
      in the same proportion to the total number of Option Shares being
      purchased as the number of Firm Shares being purchased by such
      Underwriter bears to 2,300,000, adjusted by you in such manner as to
      avoid fractional shares.  The option with respect to the Option Shares
      granted hereunder may be exercised only to cover over-allotments in the
      sale of the Firm Shares by the Underwriters.  You, as Representative of
      the several Underwriters, may cancel such option at any time prior to its
      expiration by giving written notice of such cancellation to the Company.
      To the extent, if any, that the option is exercised, payment for the
      Option Shares shall be made on the Option Closing Date in New York
      Clearing House funds by certified or bank cashier's check drawn to the
      order of the Company against delivery of certificates therefor at the
      offices of Alex. Brown & Sons Incorporated, 135 East Baltimore Street,
      Baltimore, Maryland.

      3. OFFERING BY THE UNDERWRITERS.

           It is understood that the several Underwriters are to make a public
      offering of the Firm Shares as soon as the Representative deems it
      advisable to do so.  The Firm Shares are to be initially offered to the
      public at the initial public offering price set forth in the Prospectus.
      The Representative may from time to time thereafter change the public
      offering price and other selling terms.  To the extent, if at all, that
      any Option Shares are purchased pursuant to Section 2 hereof, the
      Underwriters will offer them to the public on the foregoing terms.

           It is further understood that you will act as the Representative for
      the Underwriters in the offering and sale of the Shares in accordance
      with a Master Agreement Among Underwriters entered into by you and the
      several other Underwriters.

      4.   COVENANTS OF THE COMPANY.

           The Company covenants and agrees with the several Underwriters that:

           (a) The Company will (A) use its best efforts to cause the
      Registration Statement to become effective or, if the procedure in Rule
      430A of the Rules and Regulations is followed, to prepare and timely file
      with the Commission under Rule 424(b) of the Rules and Regulations a
      Prospectus in a form approved by the Representative containing
      information previously omitted at the time of effectiveness of 

                                      9

<PAGE>   10

      the Registration Statement in reliance on Rule 430A of the Rules and
      Regulations, and (B) not file any amendment to the Registration Statement
      or supplement to the Prospectus or document incorporated by reference
      therein of which the Representative shall not previously have been
      advised and furnished with a copy or to which the Representative shall
      have reasonably objected in writing or which is not in compliance with
      the Rules and Regulations and  (C) file on a timely basis all reports and
      any definitive proxy or information statements required to be filed by
      the Company with the Commission subsequent to the date of the Prospectus
      and prior to the termination of the offering of the Shares by the
      Underwriters.

           (b) The Company will advise the Representative promptly (A) when the
      Registration Statement or any post-effective amendment thereto shall have
      become effective, (B) of receipt of any comments from the Commission, (C)
      of any request of the Commission for amendment of the Registration
      Statement or for supplement to the Prospectus or for any additional
      information, and (D) of the issuance by the Commission of any stop order
      suspending the effectiveness of the Registration Statement or the use of
      the Prospectus or of the institution of any proceedings for that purpose.
      The Company will use its best efforts to prevent the issuance of any
      such stop order preventing or suspending the use of the Prospectus and to
      obtain as soon as possible the lifting thereof, if issued.

           (c) The Company will cooperate with the Representative in
      endeavoring to qualify the Shares for sale under the securities laws of
      such jurisdictions as the Representative may reasonably have designated
      in writing and will make such applications, file such documents, and 
      furnish such information as may be reasonably required for that purpose,
      provided the Company shall not be required to qualify as a foreign
      corporation or to file a general consent to service of process in any
      jurisdiction where it is not now so qualified or required to file such a
      consent.  The Company will, from time to time, prepare and file such
      statements, reports, and other documents, as are or may be required to
      continue such qualifications in effect for so long a period as the
      Representative may reasonably request for distribution of the Shares.

           (d) The Company will deliver to, or upon the order of, the
      Representative, from time to time, as many copies of any Preliminary
      Prospectus as the Representative may reasonably request.  The Company
      will deliver to, or upon the order of, the Representative during the
      period when delivery of a Prospectus is required under the Act, as many
      copies of the Prospectus in final form, or as thereafter amended or
      supplemented, as the Representative may reasonably request.  The Company
      will deliver to the Representative at or before the Closing Date, four
      signed copies of the Registration Statement and all amendments thereto
      including all exhibits filed therewith, and will deliver to the
      Representative such number of copies of the Registration Statement
      (including such number of copies of the exhibits filed therewith that may
      reasonably be requested), and of all amendments thereto, as the
      Representative may reasonably request.

           (e) The Company will comply with the Act and the Rules and
      Regulations, and the Securities Exchange Act of 1934 (the "Exchange
      Act"), and the rules and 


                                     10
<PAGE>   11

      regulations of the Commission thereunder, so as to permit the
      completion of the distribution of the Shares as contemplated in this
      Agreement and the Prospectus.  If during the period in which a prospectus
      is required by law to be delivered by an Underwriter or dealer, any event
      shall occur as a result of which, in the judgment of the Company or in
      the reasonable opinion of the Underwriters, it becomes necessary to amend
      or supplement the Prospectus in order to make the statements therein, in
      the light of the circumstances existing at the time the Prospectus is
      delivered to a purchaser, not misleading, or, if it is necessary at any
      time to amend or supplement the Prospectus to comply with any law, the
      Company promptly will prepare and file with the Commission an appropriate
      amendment to the Registration Statement or supplement to the Prospectus
      so that the Prospectus as so amended or supplemented will not, in the
      light of the circumstances when it is so delivered, be misleading, or so
      that the Prospectus will comply with the law.

           (f) The Company will make generally available to its security
      holders, as soon as it is practicable to do so, but in any event not
      later than 15 months after the effective date of the Registration
      Statement, an earning statement (which need not be audited) in reasonable
      detail, covering a period of at least 12 consecutive months beginning 
      after the effective date of the Registration Statement, which earning 
      statement shall satisfy the requirements of Section 11(a) of the Act and
      Rule 158 of the Rules and Regulations and will advise you in writing when
      such statement has been so made available.

           (g) The Company will, for a period of five years from the Closing
      Date, deliver to the Representative copies of annual reports and copies
      of all other documents, reports and information furnished by the Company
      to its stockholders or filed with any securities exchange pursuant to the
      requirements of such exchange or with the Commission pursuant to the Act
      or the Securities Exchange Act of 1934, as amended.  The Company will
      deliver to the Representative similar reports with respect to significant
      subsidiaries, as that term is defined in the Rules and Regulations, which
      are not consolidated in the Company's financial statements.

           (h) No offering, sale, short sale or other disposition of any shares
      of Common Stock of the Company or other securities convertible into or
      exchangeable or exercisable for shares of Common Stock or derivative of
      Common Stock (or agreement for such) will be made for a period of 180
      days after the date of this Agreement, directly or indirectly, by the
      Company otherwise than hereunder or with the prior written consent of
      Alex. Brown & Sons Incorporated.

           (i) The Company will use its best efforts to maintain the listing of
      the Shares on the Nasdaq National Market.

           (j) The Company has caused each officer, director and shareholder of
      the Company to furnish to you, on or prior to the date of this agreement,
      a letter or letters, in form and substance satisfactory to the
      Underwriters, pursuant to which each such person shall agree not to
      offer, sell, sell short or otherwise dispose of any shares of Common
      Stock of the Company or other capital stock of the Company, or any other
      securities 

                                     11

      
<PAGE>   12

      convertible, exchangeable or exercisable for Common Shares or
      derivative of Common Shares owned by such person or request the
      registration for the offer or sale of any of the foregoing (or as to
      which such person has the right to direct the disposition of) for a
      period of 180 after the date of this Agreement, directly or indirectly,
      except with the prior written consent of Alex. Brown & Sons Incorporated
      ("Lockup Agreements").

           (k) The Company shall apply the net proceeds of its sale of the
      Shares as set forth in the Prospectus and shall file such reports with
      the Commission with respect to the sale of the Shares and the application
      of the proceeds therefrom as may be required in accordance with Rule 463 
      under the Act.

           (l) The Company shall not invest, or otherwise use the proceeds
      received by the Company from its sale of the Shares in such a manner as
      would require the Company or any of the Subsidiaries to register as an
      investment company under the Investment Company Act of 1940, as amended
      (the "1940 Act").

           (m) The Company will maintain a transfer agent and, if necessary
      under the jurisdiction of incorporation of the Company, a registrar for
      the Common Stock.

           (n) The Company will not take, directly or indirectly, any action
      designed to cause or result in, or that has constituted or might
      reasonably be expected to constitute, the stabilization or manipulation
      of the price of any securities of the Company.

      5. COSTS AND EXPENSES.

           The Company will pay all costs, expenses and fees incident to the
      performance of the obligations of the Company under this Agreement,
      including, without limiting the generality of the foregoing, the
      following:  accounting fees of the Company; the fees and disbursements of
      counsel for the Company; the cost of printing and delivering to, or as
      requested by, the Underwriters copies of the Registration Statement,
      Preliminary Prospectuses, the Prospectus, this Agreement, the
      Underwriters' Selling Memorandum,  the Underwriters' Invitation Letter,
      the Blue Sky Survey, and any supplements or amendments thereto; the
      filing fees of the Commission; the filing fees and expenses (including
      legal fees and disbursements) incident to securing any required review by
      the National Association of Securities Dealers, Inc. (the "NASD") of the
      terms of the sale of the Shares; the Listing Fee of the Nasdaq National
      Market; and the expenses, including the fees and disbursements of counsel
      for the Underwriters, incurred in connection with the qualification of
      the Shares under State securities or Blue Sky laws.  The Company agrees
      to pay all costs and expenses of the Underwriters, including the fees and
      disbursements of counsel for the Underwriters, incident to the offer and
      sale of directed shares of the Common Stock by the Underwriters to
      employees and persons having business relationships with the Company and
      its Subsidiaries.  The Company shall not, however, be required to pay for
      any of the Underwriters' other expenses (other than those related to
      qualification under NASD regulation and State securities or Blue Sky
      laws) except that, if this Agreement shall not be consummated because the
      conditions in Section 6 hereof are not satisfied, or because this
      Agreement is terminated by the

                                     12
<PAGE>   13

      Representative pursuant to Section 11 hereof, or by reason of any
      failure, refusal or inability on the part of the Company to perform any
      undertaking or satisfy any condition of this Agreement or to comply with
      any of the terms hereof on its part to be performed, unless such failure
      to satisfy said condition or to comply with said terms be due to the
      default or omission of any Underwriter, then the Company shall reimburse
      the several Underwriters for reasonable out-of-pocket expenses, including
      fees and disbursements of counsel, reasonably incurred in connection with
      investigating, marketing and proposing to market the Shares or in
      contemplation of performing their obligations hereunder; but the Company
      shall not in any event be liable to any of the several Underwriters for
      damages on account of loss of anticipated profits from the sale by them
      of the Shares.

      6. CONDITIONS OF OBLIGATIONS OF THE UNDERWRITERS.

           The several obligations of the Underwriters to purchase the Firm
      Shares on the Closing Date and the Option Shares, if any, on the Option
      Closing Date are subject to the accuracy, as of the Closing Date or the
      Option Closing Date, as the case may be, of the representations and
      warranties of the Company contained herein, and to the performance by the
      Company of its covenants and obligations hereunder and to the following
      additional conditions:

           (a) The Registration Statement and all post-effective amendments
      thereto shall have become effective and any and all filings required by
      Rule 424 and Rule 430A of the Rules and Regulations shall have been made,
      and any request of the Commission for additional information (to be
      included in the Registration Statement or otherwise) shall have been
      disclosed to the Representative and complied with to their reasonable
      satisfaction.  No stop order suspending the effectiveness of the
      Registration Statement, as amended from time to time, shall have been
      issued and no proceedings for that purpose shall have been taken or, to
      the knowledge of the Company, shall be contemplated by the Commission and
      no injunction, restraining order, or order of any nature by a Federal or
      state court of competent jurisdiction shall have been issued as of the
      Closing Date which would prevent the issuance of the Shares.

           (b) The Representative shall have received on the Closing Date or
      the Option Closing Date, as the case may be, the opinion of Foley &
      Lardner, counsel for the Company, dated the Closing Date or the Option
      Closing Date, as the case may be, addressed to the Underwriters (and
      stating that it may be relied upon by counsel to the Underwriters) to the
      effect that:

                 (i) The Company has been duly organized and is validly
            existing as a corporation in good standing under the laws of the
            State of Delaware, with corporate power and authority to own or
            lease its properties and conduct its business as described in the
            Registration Statement; each of the Subsidiaries has been duly
            organized and is validly existing as a corporation in good standing
            under the laws of the jurisdiction of its incorporation, with
            corporate power and authority to own or lease its properties and
            conduct its business as described in the Registration Statement;
            the Company and each of the Subsidiaries are duly 

                                     13
<PAGE>   14

            qualified to transact business in all jurisdictions in which
            the conduct of their business requires such qualification, or in
            which the failure to qualify would have a materially adverse effect
            upon the business of the Company and the Subsidiaries taken as a
            whole; and the outstanding shares of capital stock of each of the
            Subsidiaries have been duly authorized and validly issued and are
            fully paid and non-assessable and are owned by the Company or a
            Subsidiary; and, to the best of such counsel's knowledge, the
            outstanding shares of capital stock of each of the Subsidiaries is
            owned free and clear of all liens, encumbrances and equities and
            claims, and no options, warrants or other rights to purchase,
            agreements or other obligations to issue or other rights to convert
            any obligations into any shares of capital stock or of ownership
            interests in the Subsidiaries are outstanding.

                 (ii) The Company has authorized and outstanding capital stock
            as set forth under the caption "Capitalization" in the Prospectus;
            the authorized shares of the Company's Common Stock have been duly
            authorized; the outstanding shares of the Company's Common Stock
            have been duly authorized and validly issued and are fully paid and
            non-assessable; all of the Shares conform to the description
            thereof contained in the Prospectus; the certificates for the
            Shares, assuming they are in the form filed with the Commission,
            are in due and proper form; the shares of Common Stock, including
            the Option Shares, if any, to be sold by the Company pursuant to
            this Agreement have been duly authorized and will be validly
            issued, fully paid and non-assessable when issued and paid for as
            contemplated by this Agreement; and no preemptive rights of
            stockholders exist with respect to any of the Shares or the issue
            or sale thereof.

                 (iii) Except as described in or contemplated by the
            Prospectus, to the knowledge of such counsel, there are no
            outstanding securities of the Company convertible or exchangeable
            into or evidencing the right to purchase or subscribe for any
            shares of capital stock of the Company and there are no outstanding
            or authorized options, warrants or rights of any character
            obligating the Company to issue any shares of its capital stock or
            any securities convertible or exchangeable into or evidencing the
            right to purchase or subscribe for any shares of such stock; and 
            except as described in the Prospectus, to the knowledge of such 
            counsel, no holder of any securities of the Company or any other 
            person has the right, contractual or otherwise, which has not been
            satisfied or effectively waived,  to cause the Company to sell or 
            otherwise issue to them, or to permit them to underwrite the sale 
            of, any of the Shares or the right to have any Common Shares or 
            other securities of the Company included in the Registration 
            Statement or the right, as a result of the filing of the 
            Registration Statement, to require registration under the Act of 
            any shares of Common Stock or other securities of the Company.

                 (iv) The Registration Statement has become effective under the
            Act and, to the best of the knowledge of such counsel, no stop
            order proceedings with respect thereto have been instituted or are
            pending or threatened under the Act.

                                     14
<PAGE>   15

                 (v) The Registration Statement, the Prospectus and each
            amendment or supplement thereto and document incorporated by
            reference therein comply as to form in all material respects with
            the requirements of the Act or the Securities Exchange Act of 1934,
            as applicable and the applicable rules and regulations thereunder
            (except that such counsel need express no opinion as to the
            financial statements and related schedules therein).

                 (vi) The statements under the captions "Business,"
            "Management," "Certain Transactions," "Description of Capital
            Stock" and "Shares Eligible for Future Sale" in the Prospectus,
            insofar as such statements constitute a summary of documents
            referred to therein or matters of law, fairly summarize in all
            material respects the information called for with respect to such
            documents and matters.

                 (vii) Such counsel does not know of any contracts or documents
            required to be filed as exhibits to the Registration Statement or
            described in the Registration Statement or the Prospectus which are
            no so filed, or described as required, and such contracts and
            documents as are summarized in the Registration Statement or the
            Prospectus are fairly summarized in all material respects.

                 (viii) Such counsel knows of no material legal or governmental
            proceedings pending or threatened against the Company or any of the
            Subsidiaries except as set forth in the Prospectus.

                 (ix) The execution and delivery of this Agreement and the
            consummation of the transactions herein contemplated do not and
            will not conflict with or result in a breach of any of the terms or
            provisions of, or constitute a default under, the Charter or
            by-laws of the Company, or any agreement or instrument known to
            such counsel to which the Company or any of the Subsidiaries is a
            party or by which the Company or any of the Subsidiaries may be
            bound.

                 (x) This Agreement has been duly authorized, executed and
            delivered by the Company.

                 (xi) No approval, consent, order, authorization, designation,
            declaration or filing by or with any regulatory, administrative or
            other governmental body is necessary in connection with the
            execution and delivery of this Agreement and the consummation of
            the transactions herein contemplated (other than as may be required
            by the NASD or as required by State securities and Blue Sky laws as
            to which such counsel need express no opinion) except such as have
            been obtained or made, specifying the same.

                 (xii) The Company is not, and will not become, as a result of
            the consummation of the transactions contemplated by this
            Agreement, and application of the net proceeds therefrom as
            described in the Prospectus, required to register as an investment
            company under the 1940 Act.

                                     15

<PAGE>   16
           In addition to the matters set forth above, such opinion shall also
      include a statement to the effect that nothing has come to the attention
      of such counsel which leads them to believe that (i) the Registration
      Statement, at the time it became effective under the Act (but after
      giving effect to any modifications incorporated therein pursuant to Rule
      430A under the Act) and as of the Closing Date or the Option Closing
      Date, as the case may be, contained an untrue statement of a material
      fact or omitted to state a material fact required to be stated therein or
      necessary to make the statements therein not misleading, and (ii) the
      Prospectus, or any supplement thereto, on the date it was filed pursuant
      to the Rules and Regulations and as of the Closing Date or the Option
      Closing Date, as the case may be, contained an untrue statement of a
      material fact or omitted to state a material fact necessary in order to
      make the statements, in the light of the circumstances under which they
      are made, not misleading (except that such counsel need express no view
      as to financial statements, schedules and statistical information
      therein).  With respect to such statement, Foley & Lardner may state that
      their belief is based upon the procedures set forth therein, but is
      without independent check and verification.

           (c) The Representative shall have received from Greenberg, Traurig,
      Hoffman, Lipoff, Rosen & Quentel, P.A. ("Greenberg, Traurig"), counsel
      for the Underwriters, an opinion dated the Closing Date or the Option
      Closing Date, as the case may be, substantially to the effect specified
      in subparagraphs (ii), (iii), (iv) and (ix) of Paragraph (b) of this
      Section 6, and that the Company is a duly organized and validly existing
      corporation under the laws of the State of Delaware.  In addition to the
      matters set forth above, such opinion shall also include a statement to
      the effect that nothing has come to the attention of such counsel which
      leads them to believe that (i) the Registration Statement, or any
      amendment thereto, as of the time it became effective under the Act (but
      after giving effect to any modifications incorporated therein pursuant to
      Rule 430A under the Act) as of the Closing Date or the Option Closing
      Date, as the case may be, contained an untrue statement of a material
      fact or omitted to state a material fact required to be stated therein or
      necessary to make the statements therein not misleading, and (ii) the
      Prospectus, or any supplement thereto, on the date it was filed pursuant
      to the Rules and Regulations and as of the Closing Date or the Option
      Closing Date, as the case may be, contained an untrue statement of a
      material fact or omitted to state a material fact, necessary in order to
      make the statements, in the light of the circumstances under which they
      are made, not misleading (except that such counsel need express no view
      as to financial statements, schedules and statistical information
      therein).  With respect to such statement, may state that their belief is
      based upon the procedures set forth therein, but is without independent
      check and verification.

           (d) The Representative shall have received at or prior to the
      Closing Date from Greenberg, Traurig a memorandum or summary, in form and
      substance satisfactory to the Representative, with respect to the
      qualification for offering and sale by the Underwriters of the Shares
      under the State securities or Blue Sky laws of such jurisdictions as the
      Representative may reasonably have designated to the Company.

                                     16
<PAGE>   17

           (e) You shall have received, on each of the dates hereof, the
      Closing Date and the Option Closing Date, as the case may be, a letter
      dated the date hereof, the Closing Date or the Option Closing Date, as
      the case may be, in form and substance satisfactory to you, of Deloitte &
      Touche LLP that they are independent public accountants within the
      meaning of the Act and the applicable published Rules and Regulations
      thereunder and stating that in their opinion the financial statements and
      schedules examined by them and included in the Registration Statement
      comply in form in all material respects with the applicable accounting
      requirements of the Act and the related published Rules and Regulations;
      and containing such other statements and information as is ordinarily
      included in accountants' "comfort letters" to Underwriters with respect
      to the financial statements and certain financial and statistical 
      information contained in the Registration Statement and Prospectus.

           (f) The Representative shall have received on the Closing Date or
      the Option Closing Date, as the case may be, a certificate or
      certificates of the Chief Executive Officer and the Chief Financial
      Officer of the Company to the effect that, as of the Closing Date or the
      Option Closing Date, as the case may be, each of them severally
      represents as follows:

                 (i) The Registration Statement has become effective under the
            Act and no stop order suspending the effectiveness of the
            Registrations Statement has been issued, and no proceedings for
            such purpose have been taken or are, to his knowledge, contemplated
            by the Commission;

                 (ii) The representations and warranties of the Company
            contained in Section 1 hereof are true and correct as of the
            Closing Date or the Option Closing Date, as the case may be;

                 (iii) All filings required to have been made pursuant to Rules
            424 or 430A under the Act have been made;

                 (iv) He has carefully examined the Registration Statement and
            the Prospectus and, in his opinion, as of the effective date of the
            Registration Statement, the statements contained in the
            Registration Statement were true and correct, and such Registration
            Statement and Prospectus did not omit to state a material fact
            required to be stated therein or necessary in order to make the
            statements therein not misleading, and since the effective date of
            the Registration Statement, no event has occurred which should have
            been set forth in a supplement to or an amendment of the Prospectus
            which has not been so set forth in such supplement or amendment;
            and

                 (v) Since the respective dates as of which information is
            given in the Registration Statement and Prospectus, there has not
            been any material adverse change or any development involving a
            prospective material adverse change in or affecting the condition,
            financial or otherwise, of the Company and its Subsidiaries taken
            as a whole or the earnings, business, management, properties,

                                     17
<PAGE>   18
            assets, rights, operations, condition (financial or otherwise) or
            prospects of the Company and the Subsidiaries taken as a whole,
            whether or not arising in the ordinary course of business.

           (g) The Company shall have furnished to the Representative such
      further certificates and documents confirming the representations and
      warranties, covenants and conditions contained herein and related matters
      as the Representative may reasonably have requested.

           (h) The Firm Shares and Option Shares, if any, have been approved
      for designation upon notice of issuance on the Nasdaq National Market.

           (i) The Lockup Agreements described in Section 4 (j) (x) are in full
      force and effect.

           The opinions and certificates mentioned in this Agreement shall be
      deemed to be in compliance with the provisions hereof only if they are in
      all material respects satisfactory to the Representative and to
      Greenberg, Traurig, counsel for the Underwriters.

           If any of the conditions hereinabove provided for in this Section 6
      shall not have been fulfilled when and as required by this Agreement to
      be fulfilled, the obligations of the Underwriters hereunder may be
      terminated by the Representative by notifying the Company of such
      termination in writing or by telegram at or prior to the Closing Date or
      the Option Closing Date, as the case may be.

           In such event, the Company and the Underwriters shall not be under
      any obligation to each other (except to the extent provided in Sections 5
      and 8 hereof).

      7. CONDITIONS OF THE OBLIGATIONS OF THE COMPANY.

           The obligations of the Company to sell and deliver the portion of
      the Shares required to be delivered as and when specified in this
      Agreement are subject to the conditions that at the Closing Date or the
      Option Closing Date, as the case may be, no stop order suspending the
      effectiveness of the Registration Statement shall have been issued and in
      effect or proceedings therefor initiated or threatened.

      8. INDEMNIFICATION.

           (a) The Company agrees to indemnify and hold harmless each
      Underwriter and each person, if any, who controls any Underwriter within
      the meaning of the Act, against any losses, claims, damages or
      liabilities to which such Underwriter or any such controlling person may
      become subject under the Act or otherwise, insofar as such losses,
      claims, damages or liabilities (or actions or proceedings in respect
      thereof) arise out of or are based upon  (i) any untrue statement or
      alleged untrue statement of any material fact contained in the
      Registration Statement, any Preliminary Prospectus, the Prospectus or 

                                     18
<PAGE>   19

      any amendment or supplement thereto, or  (ii) the omission or alleged
      omission to state therein a material fact required to be stated therein
      or necessary to make the statements therein not misleading; and will
      reimburse each Underwriter and each such controlling person upon demand
      for any legal or other expenses reasonably incurred by such Underwriter
      or such controlling person in connection with investigating or defending
      any such loss, claim, damage or liability, action or proceeding or in
      responding to a subpoena or governmental inquiry related to the offering
      of the Shares, whether or not such Underwriter or controlling person is a
      party to any action or proceeding; provided, however, that the Company
      will not be liable in any such case to the extent that any such loss,
      claim, damage or liability arises out of or is based upon an untrue
      statement or alleged untrue statement, or omission or alleged omission
      made in the Registration Statement, any Preliminary Prospectus, the
      Prospectus, or such amendment or supplement, in reliance upon and in
      conformity with written information furnished to the Company by or
      through the Representative specifically for use in the preparation
      thereof. This indemnity agreement will be in addition to any liability
      which the Company may otherwise have.

           (b) Each Underwriter severally and not jointly will indemnify and
      hold harmless the Company, each of its directors, each of its officers
      who have signed the Registration Statement, and each person, if any, who
      controls the Company within the meaning of the Act, against any losses,
      claims, damages or liabilities to which the Company or any such director,
      officer, or controlling person may become subject under the Act or
      otherwise, insofar as such losses, claims, damages or liabilities (or
      actions or proceedings in respect thereof) arise out of or are based upon
      (i)  any untrue statement or alleged  untrue statement of any material
      fact contained in the Registration Statement, any Preliminary Prospectus,
      the Prospectus or any amendment or supplement thereto, or (ii) the
      omission or the alleged omission to state therein a material fact
      required to be stated therein or necessary to make the statements therein
      not misleading in the light of the  circumstances under which they were
      made; and will reimburse any legal or other expenses reasonably incurred
      by the Company or any such director, officer, or controlling person in
      connection with investigating or defending any such loss, claim, damage,
      liability, action or proceeding; provided, however, that each Underwriter
      will be liable in each case to the extent, but only to the extent, that
      such untrue statement or alleged untrue statement or omission or alleged
      omission has been made in the Registration Statement, any Preliminary
      Prospectus, the Prospectus or such amendment or supplement, in reliance
      upon and in conformity with written information furnished to the Company
      by or through the Representative specifically for use in the preparation
      thereof.  This indemnity agreement will be in addition to any liability
      which such Underwriter may otherwise have.

           (c) In case any proceeding (including any governmental
      investigation) shall be instituted involving any person in respect of
      which indemnity may be sought pursuant to this Section 8, such person
      (the "indemnified party") shall promptly notify the person against whom
      such indemnity may be sought (the "indemnifying party") in writing.  No
      indemnification provided for in Section 8(a) or (b) shall be available to
      any party who 

                                     19
<PAGE>   20

      shall fail to give notice as provided in this Section 8(c) if the party
      to whom notice was not given was unaware of the proceeding to which such
      notice would have related and was materially prejudiced by the failure to
      give such notice, but the failure to give such notice shall not relieve
      the indemnifying party or parties from any liability which it or they may
      have to the indemnified party for contribution or otherwise than on
      account of the provisions of Section 8(a) or (b).  In case any such
      proceeding shall be brought against any indemnified party and it shall
      notify the indemnifying party of the commencement thereof, the
      indemnifying party shall be entitled to participate therein and, to the
      extent that it shall wish, jointly with any other indemnifying party
      similarly notified, to assume the defense thereof, with counsel
      satisfactory to such indemnified party and shall pay as incurred the fees
      and disbursements of such counsel related to such proceeding.  In any
      such proceeding, any indemnified party shall have the right to retain its
      own counsel at its own expense.  Notwithstanding the foregoing, the
      indemnifying party shall pay as incurred (or within 30 days of
      presentation) the fees and expenses of the counsel retained by the
      indemnified party in the event  (i) the indemnifying party and the
      indemnified party shall have mutually agreed to the retention of such
      counsel,  (ii) the named parties to any such proceeding (including any
      impleaded parties) include both the indemnifying party and the
      indemnified party and representation of both parties by the same counsel
      would be inappropriate due to actual or potential differing interests
      between them or (iii) the indemnifying party shall have failed to assume
      the defense and employ counsel acceptable to the indemnified party within
      a reasonable period of time after notice of commencement of the action.
      It is understood that the indemnifying party shall not, in connection
      with any proceeding or related proceedings in the same jurisdiction, be
      liable for the reasonable fees and expenses of more than one separate
      firm for all such indemnified parties.  Such firm shall be designated in
      writing by you in the case of parties indemnified pursuant to Section
      8(a) and by the Company in the case of parties indemnified pursuant to
      Section 8(b).  The indemnifying party shall not be liable for any
      settlement of any proceeding effected without its written consent but if
      settled with such consent or if there be a final judgment for the
      plaintiff, the indemnifying party agrees to indemnify the indemnified
      party from and against any loss or liability by reason of such settlement
      or judgment.  In addition, the indemnifying party will not, without the
      prior written consent of the indemnified party, settle or compromise or
      consent to the entry of any judgment in any pending or threatened claim,
      action or proceeding of which indemnification may be sought hereunder
      (whether or not any indemnified party is an actual or potential party to 
      such claim, action or proceeding) unless such settlement, compromise or 
      consent includes an unconditional release of each indemnified party from 
      all liability arising out of such claim, action or proceeding.

           (d) If the indemnification provided for in this Section 8 is
      unavailable to or insufficient to hold harmless an indemnified party
      under Section 8(a) or (b) above in respect of any losses, claims, damages
      or liabilities (or actions or proceedings in respect thereof) referred to
      therein, then each indemnifying party shall contribute to the amount paid
      or payable by such indemnified party as a result of such losses, claims,
      damages or liabilities (or actions or proceedings in respect thereof) in
      such proportion as is appropriate to reflect the relative benefits
      received by the Company on the one hand and 

                                     20
<PAGE>   21

      the Underwriters on the other from the offering of the Shares.  If,
      however, the allocation provided by the immediately preceding sentence is
      not permitted by applicable law then each indemnifying party shall
      contribute to such amount paid or payable by such indemnified party in
      such proportion as is appropriate to reflect not only such relative
      benefits but also the relative fault of the Company on the one hand and
      the Underwriters on the other in connection with the statements or
      omissions which resulted in such losses, claims, damages or liabilities,
      (or actions or proceedings in respect thereof), as well as any other
      relevant equitable considerations. The relative benefits received by the
      Company on the one hand and the Underwriters on the other shall be deemed
      to be in the same proportion as the total net proceeds from the offering
      (before deducting expenses) received by the Company bear to the total
      underwriting discounts and commissions received by the Underwriters, in
      each case as set forth in the table on the cover page of the Prospectus. 
      The relative fault shall be determined by reference to, among other
      things, whether the untrue or alleged untrue statement of a material fact
      or the omission or alleged omission to state a material fact relates to
      information supplied by the Company on the one hand or the Underwriters
      on the other and the parties' relative intent, knowledge, access to
      information and opportunity to correct or prevent such statement or
      omission.

           The Company, and the Underwriters agree that it would not be just
      and equitable if contributions pursuant to this Section 8(d) were
      determined by pro rata allocation (even if the Underwriters were treated
      as one entity for such purpose) or by any other method of allocation
      which does not take account of the equitable considerations referred to
      above in this Section 8(d).  The amount paid or payable by an indemnified
      party as a result of the losses, claims, damages or liabilities (or
      actions or proceedings in respect thereof) referred to above in this
      Section 8(d) shall be deemed to include any legal or other expenses
      reasonably incurred by such indemnified party in connection with
      investigating or defending any such action or claim.  Notwithstanding
      the provisions of this subsection (d),  (i) no Underwriter shall be
      required to contribute any amount in excess of the underwriting discounts
      and commissions applicable to the Shares purchased by such Underwriter,
      and  (ii) no person guilty of fraudulent misrepresentation shall be
      entitled to contribution from any person who was not guilty of such
      fraudulent misrepresentation.  The Underwriters' obligations in this
      Section 8(d) to contribute are several in proportion to their respective
      underwriting obligations and not joint.

           (e) In any proceeding relating to the Registration Statement, any
      Preliminary Prospectus, the Prospectus or any supplement or amendment
      thereto, each party against whom contribution may be sought under this
      Section 8 hereby consents to the jurisdiction of any court having
      jurisdiction over any other contributing party, agrees that process
      issuing from such court may be served upon him or it by any other
      contributing party and consents to the service of such process and agrees
      that any other contributing party may join him or it as an additional
      defendant in any such proceeding in which such other contributing party
      is a party.

                                     21
<PAGE>   22

           (f) Any losses, claims, damages, liabilities or expenses for which
      an indemnified party is entitled to indemnification or contribution under
      this Section 8 shall be paid by the indemnifying party to the indemnified
      party as such losses, claims, damages, liabilities or expenses are
      incurred.  The indemnity and contribution agreements contained in this
      Section 8 and the representations and warranties of the Company set forth
      in this Agreement shall remain operative and in full force and effect,
      regardless of (i) any investigation made by or on behalf of any
      Underwriter or any person controlling any Underwriter, the Company, its
      directors or officers or any persons controlling the Company, (ii)
      acceptance of any Shares and payment therefor hereunder, and (iii) any
      termination of this Agreement.  A successor to any Underwriter, or to the
      Company, its directors or officers, or any person controlling the
      Company, shall be entitled to the benefits of the indemnity, contribution
      and reimbursement agreements contained in this Section 8.

      9. DEFAULT BY UNDERWRITERS.

           If on the Closing Date or the Option Closing Date, as the case may
      be, any Underwriter shall fail to purchase and pay for the portion of the
      Shares which such Underwriter has agreed to purchase and pay for on such
      date (otherwise than by reason of any default on the part of the
      Company), you, as Representative of the Underwriters, shall use your
      reasonable efforts to procure within 36 hours thereafter one or more of
      the other Underwriters, or any others, to purchase from the Company such
      amounts as may be agreed upon and upon the terms set forth herein, the
      Firm Shares or Option Shares, as the case may be, which the defaulting
      Underwriter or Underwriters failed to purchase.  If during such 36 hours 
      you, as such Representative, shall not have procured such other
      Underwriters, or any others, to purchase the Firm Shares or Option
      Shares, as the case may be, agreed to be purchased by the defaulting
      Underwriter or Underwriters, then  (a) if the aggregate number of shares
      with respect to which such default shall occur does not exceed 10% of the
      Firm Shares or Option Shares, as the case may be, covered hereby, the
      other Underwriters shall be obligated, severally, in proportion to the
      respective numbers of Firm Shares or Option Shares, as the case may be,
      which they are obligated to purchase hereunder, to purchase the Firm
      Shares or Option Shares, as the case may be, which such defaulting
      Underwriter or Underwriters failed to purchase, or (b) if the aggregate
      number of shares of Firm Shares or Option Shares, as the case may be,
      with respect to which such default shall occur exceeds 10% of the Firm
      Shares or Option Shares, as the case may be, covered hereby, the Company
      or you as the Representative of the Underwriters will have the right, by
      written notice given within the next 36-hour period to the parties to
      this Agreement, to terminate this Agreement without liability on the part
      of the non-defaulting Underwriters or of the Company except to the extent
      provided in Section 8 hereof.  In the event of a default by any
      Underwriter or Underwriters, as set forth in this Section 9, the Closing
      Date or Option Closing Date, as the case may be, may be postponed for
      such period, not exceeding seven days, as you, as Representative, may
      determine in order that the required changes in the Registration
      Statement or in the Prospectus or in any other documents or arrangements
      may be effected.  The term "Underwriter" includes any person substituted
      for a defaulting Underwriter.  Any action taken under this Section 9


                                     22
<PAGE>   23

      shall not relieve any defaulting Underwriter from liability in respect of
      any default of such Underwriter under this Agreement.

      10. NOTICES.

           All communications hereunder shall be in writing and, except as
      otherwise provided herein, will be mailed, delivered, telecopied or
      telegraphed and confirmed as follows:  if to the Underwriters, to Alex.
      Brown & Sons Incorporated, 135 East Baltimore Street, Baltimore, Maryland
      21202, Attention:  William M. Legg; with a copy to Alex. Brown & Sons
      Incorporated, 135 East Baltimore Street, Baltimore, Maryland 21202.
      Attention: General Counsel; if to the Company, to Trailer Bridge, Inc.,
      9550 Regency Square Boulevard, Suite 500, Jacksonville, Florida  32225,
      Attention: President.

      11. TERMINATION.

           This Agreement may be terminated by you by notice to the Company as
      follows:

           (a) at any time prior to the earlier of  (i) the time the Shares are
      released by you for sale by notice to the Underwriters, or  (ii) 11:30
      a.m. on the first business day following the date of this Agreement;

           (b) at any time prior to the Closing Date if any of the following
      has occurred: (i) since the respective dates as of which information is
      given in the Registration Statement and the Prospectus, any material
      adverse change or any development involving a prospective material
      adverse change in or affecting the condition, financial or otherwise, of
      the Company and its Subsidiaries taken as a whole or the earnings,
      business, management, properties, assets, rights, operations, condition
      (financial or otherwise) or prospects of the Company and its Subsidiaries
      taken as a whole, whether or not arising in the ordinary course of
      business, (ii) any outbreak or escalation of hostilities or declaration
      of war or national emergency or other national or international calamity
      or crisis or change in economic or political conditions if the effect of
      such outbreak, escalation, declaration, emergency, calamity, crisis or
      change on the financial markets of the United States would, in your
      reasonable judgment, make it impracticable to market the Shares or to
      enforce contracts for the sale of the Shares, or (iii) suspension of
      trading in securities generally on the New York Stock Exchange or the
      American Stock Exchange or limitation on prices (other than limitations
      on hours or numbers of days of trading) for securities on either such
      Exchange, (iv) the enactment, publication, decree or other promulgation
      of any statute, regulation, rule or order of any court or other
      governmental authority which in your opinion materially and adversely
      affects or may materially and adversely affect the business or operations
      of the Company, (v) declaration of a banking moratorium by United States
      or New York State authorities, (vi) any downgrading in the rating of the
      Company's debt securities by any "nationally recognized statistical
      rating organization" (as defined for purposes of Rule 436(g) under the
      Exchange Act); (vii) the suspension of trading of the Company's common
      stock by the Commission on the Nasdaq National Market; or (viii) the
      taking of any action by any governmental body or agency in 


                                     23
<PAGE>   24

      respect of its monetary or fiscal affairs which in your reasonable 
      opinion has a material adverse effect on the securities markets in the 
      United States; or

           (c) as provided in Sections 6 and 9 of this Agreement.

      12. SUCCESSORS.

           This Agreement has been and is made solely for the benefit of the
      Underwriters and, the Company and their respective successors, executors,
      administrators, heirs and assigns, and the officers, directors and
      controlling persons referred to herein, and no other person will have any
      right or obligation hereunder.  No purchaser of any of the Shares from
      any Underwriter shall be deemed a successor or assign merely because of 
      such purchase.

      13. INFORMATION PROVIDED BY UNDERWRITERS.                             

           The Company and the Underwriters acknowledge and agree that the only
      information furnished or to be furnished by any Underwriter to the
      Company for inclusion in any Prospectus or the Registration Statement
      consists of the information set forth in the last paragraph on the front
      cover page (insofar as such information relates to the Underwriters),
      legends required by Item 502(d) of Regulation S-K under the Act and the
      information under the caption "Underwriting" in the Prospectus.

      14. MISCELLANEOUS.

           The reimbursement, indemnification and contribution agreements
      contained in this Agreement and the representations, warranties and
      covenants in this Agreement shall remain in full force and effect
      regardless of  (a) any termination of this Agreement,  (b) any
      investigation made by or on behalf of any Underwriter or controlling
      person thereof, or by or on behalf of the Company or its directors or
      officers and  (c) delivery of and payment for the Shares under this
      Agreement.

           This Agreement may be executed in two or more counterparts, each of
      which shall be deemed an original, but all of which together shall
      constitute one and the same instrument.

           This Agreement shall be governed by, and construed in accordance
      with, the laws of the State of Maryland.

                                      24
<PAGE>   25

           If the foregoing letter is in accordance with your understanding of
      our agreement, please sign and return to us the enclosed duplicates
      hereof, whereupon it will become a binding agreement among the Company
      and the several Underwriters in accordance with its terms.

                                        Very truly yours,                     
                                                                               
                                        TRAILER BRIDGE, INC.                  
                                                                               
                                                                               
                                        By:                                   
                                           ------------------------------------
                                           John McCown                        
                                           Chairman and Chief Executive Officer

The foregoing Underwriting
Agreement is hereby confirmed
and accepted as of the date
first above written.

ALEX. BROWN & SONS INCORPORATED


As Representative of the
several Underwriters listed
on Schedule I




By:
   ---------------------------- 
   Authorized Officer


                                      25
        
<PAGE>   26


                                   SCHEDULE I



                            SCHEDULE OF UNDERWRITERS



<TABLE>
<CAPTION>
                                 NUMBER OF FIRM SHARES
          UNDERWRITER               TO BE PURCHASED
          -----------               ---------------
<S>                              <C>
Alex. Brown & Sons Incorporated
                                           -----------
   Total                                   [2,700,000]
                                           ==========
</TABLE>



                                      26

<PAGE>   1
                                                                   EXHIBIT 3.1


                              AMENDED AND RESTATED
                          CERTIFICATE OF INCORPORATION
                                       OF
                              TRAILER BRIDGE, INC.

         Trailer Bridge, Inc., a Delaware corporation (originally incorporated
as Trailer Bridge Corporation), hereby amends and restates its Certificate of
Incorporation, initially filed with the Delaware Secretary of State on April 1,
1991 and thereafter amended from time to time. This Amended and Restated
Certificate of Incorporation restates and integrates and further amends the
original Certificate of Incorporation, as previously amended. This Amended and
Restated Certificate of Incorporation was duly adopted by the Corporation's
Board of Directors acting by unanimous written consent pursuant to Section 141
of the General Corporation Law of the State of Delaware (the "GCL") and duly
adopted by the Corporation's stockholders, acting by written consent pursuant
to Section 228 of the GCL, all in accordance with Sections 242 and 245 of the
GCL. This Amended and Restated Certificate of Incorporation shall be effective
as of the date of its filing with the Delaware Secretary of State. This Amended
and Restated Certificate of Incorporation supersedes and replaces the
heretofore existing Certificate of Incorporation of the Corporation and
provides in its entirety as follows:

                                   ARTICLE 1
                        
            The name of the Corporation is "Trailer Bridge, Inc."


                                   ARTICLE 2

            The Corporation shall have perpetual existence.

                                   ARTICLE 3
            
         The purpose of the Corporation is to engage in any lawful act or
activity for which a corporation may be organized under GCL.

                                   ARTICLE 4
            
         4.1 The total number of shares of all classes of stock which the
Corporation is authorized to have outstanding at any one time is 21,000,000
shares, of which 1,000,000 shares shall be preferred stock, par value $0.01 per
share,(the "Preferred Stock"), and 20,000,000 shares shall be common stock, par
value $0.01 per share (the "Common Stock"). All or any part of the Common Stock
and Preferred Stock may be issued by the Corporation from time to time and for
such consideration as the Board of Directors may determine. All of such shares,
if and when issued, and upon receipt of such consideration by the Corporation,
shall be fully paid and non-assessable.
<PAGE>   2

         4.2 The Board of Directors is expressly authorized at any time and
from time to time to divide the Preferred Stock into one or more classes or
series and to fix and determine the relative powers, preferences and rights,
and the qualifications, limitations and restrictions thereof, of the shares of
any class or series so established. All shares of any one class or series of
Preferred Stock shall be identical, except as to the dates of issue and the
dates from which dividends on shares of the series issued on different dates
will cumulate, if cumulative. The Board of Directors is hereby expressly
authorized to fix by resolution or resolutions establishing and designating
each such class or series, the number of shares which shall constitute such
class or series, and the relative powers, preferences and rights, and the
qualifications, limitations and restrictions thereof, as shall be stated and
expressed in the resolution or resolutions adopted by the Board of Directors
providing for the issuance of such class or series and as may be permitted by
the GCL, which relative powers, preferences, rights, qualifications,
limitations and restrictions may differ with respect to each class or series as
to:

               (a)  The rate or manner of any dividends, including whether and
          to the extent such dividends shall be cumulative, participating, or
          both, the conditions and dates upon which such dividends shall be
          payable, and the preference, if any, or relation which such dividends
          shall bear to the dividends payable on any other class or classes of
          stock or any other series of any class or classes of stock of the
          Corporation;

               (b)  Whether the shares of such class or series shall be subject
          to redemption by the Corporation and, if so, the redemption price,
          the time or times of redemption and the terms and conditions of
          redemption, which price, times of redemption and terms and conditions
          may differ in the event of mandatory redemption or permissive
          redemption;

               (c)  The rights of the shares of such class or series in the
          event of voluntary or involuntary liquidation, dissolution or winding
          up of the Corporation and the relative rights of priority, if any, of
          payment of shares of that class or series;

               (d)  Sinking fund provisions, if any, for the redemption or
          purchase of shares of such class or series;

               (e)  Whether the shares of such class or series shall be
          convertible into or exchangeable for shares of any other class or
          classes of stock or any other series of any class or classes of stock
          of the Corporation, and, if provision be made for conversion or
          exchange, the times, prices, rates adjustments and other terms and
          conditions of such conversion or exchange;

               (f)  The restrictions, if any, on the issue of any additional
          shares or reissue of shares of such class or series of Preferred
          Stock;

               (g)  Voting rights, if any; and

                                       2
<PAGE>   3

               (h)  Any other such relative powers, preferences or rights, and
          the qualifications, limitations or restrictions thereof for such
          class or series which the GCL now or hereafter empowers or permits
          the Board of Directors to determine.

Except as otherwise provided by the GCL, each outstanding share of Common Stock
and each outstanding share of Preferred Stock with respect to which the
resolution or resolutions adopted by the Board of Directors of the Corporation
in accordance with this Article 4 provide that such class or series shall vote
together with the Common Stock on the matters specified in such resolution
shall be entitled to vote on such matters together as a single class. Each
holder of shares of Common Stock shall be entitled to one vote for each such
share held by such stockholder on all matters on which such shares are entitled
to vote.

         4.3 Subject to the provisions of this Article 4 and any resolution or
resolutions adopted by the Board of Directors as provided in this Article 4
with respect to the designations, preferences, rights, qualifications,
limitations and restrictions relating to any class or series of Preferred
Stock, (i) the Board of Directors of the Corporation may cause dividends to be
paid to the holders of shares of Common Stock out of funds legally available
therefor by declaring an amount per share as a dividend and (ii) in the event
of any voluntary or involuntary liquidation, dissolution or winding up of the
Corporation, the holders of shares of Common Stock shall be entitled to share
in all remaining assets of the Corporation available for distribution to its
stockholders.

         4.4 On the effective date of this Amended and Restated Certificate of
Incorporation, each share of the Corporation's common stock, par value $1.00
per share, outstanding on such date shall be divided and changed into 15,700
fully paid and nonassessable shares of Common Stock, par value $0.01 per share,
and each holder of record shall be entitled to exchange his or her certificates
for new certificates representing the new number of shares of new Common Stock.

                                   ARTICLE 5

          5.1  DEFINITIONS. For purposes of this Article 5, the following terms
shall have the meanings specified below:

               (a)  A Person shall be deemed to be the "Beneficial Owner" of,
or to "Beneficially Own" shares of Common Stock to the extent such Person would
be deemed to be the beneficial owner thereof pursuant to Rule 13d-3 promulgated
by the Securities and Exchange Commission under the Securities Exchange Act of
1934, as such rule may be amended from time to time.

               (b)  "Citizen" shall mean, at all tiers of ownership and in both
form and substance at each tier of ownership:

                                       3

<PAGE>   4

                    (1)  any individual who is a citizen of the United States,
          by birth, naturalization or as otherwise authorized by law;

                    (2)  any corporation (i) that is organized under the laws
          of the United States or of a state, territory, district or possession
          thereof, (ii) of which title to not less than 75% of its stock is
          Beneficially Owned by and vested in Persons who are Citizens, as
          defined herein, free from any trust or fiduciary obligation in favor
          of Non-Citizens, as defined herein, (iii) of which not less than 75%
          of the voting power is vested in Citizens, as defined herein, free
          from any contract or understanding through which it is arranged that
          such voting power may be exercised directly or indirectly on behalf
          of Non-Citizens, as defined herein, (iv) of which there are no other
          means by which control is conferred upon or permitted to be exercised
          by Non-Citizens, as defined herein, (v) whose president or chief
          executive officer, chairman of the Board of Directors and all
          officers authorized to act in the absence or disability of such
          Persons are Citizens, as defined herein, and (vi) of which more than
          50% of that number of its directors necessary to constitute a quorum
          are Citizens, as defined herein;

                    (3)  any partnership (i) that is organized under the laws
          of the United States or of a state, territory, district or possession
          thereof, (ii) all general partners of which are Citizens, as defined
          herein, and (iii) of which not less than a 75% interest is
          Beneficially Owned and controlled by, and vested in, Persons who are
          Citizens, as defined herein, free and clear of any trust or fiduciary
          obligation in favor of any Non-Citizens, as defined herein;

                    (4)  any association (i) that is organized under the laws
          of the United States, or of a state, territory, district or
          possession thereof, (ii) of which 100% of the members are Citizens,
          as defined herein, (iii) whose president or other chief executive
          officer (or equivalent position), chairman of the Board of Directors
          (or equivalent committee or body) and all Persons authorized to act
          in the absence or disability of such Persons are Citizens, as defined
          herein, (iv) of which not less than 75% of the voting power is vested
          in Citizens, as defined herein, free and clear of any trust or
          fiduciary obligation in favor of any Non-Citizens, as defined herein,
          and (v) of which more than 50% of that number of its directors (or
          equivalent Persons) necessary to constitute a quorum are Citizens as
          defined herein;

                    (5)  any limited liability company (i) that is organized
          under the laws of the United States, or of a state, territory,
          district or possession thereof, (ii) of which 75% of the members are
          Citizens, as defined herein, and the remaining members are Persons
          meeting the requirements of 46 U.S.C. Sec.12102(a), (iii) whose
          president or other chief executive officer (or equivalent position),
          chairman of the Board of Directors (or equivalent committee or body)
          and all Persons authorized to act in the absence or disability of
          such Persons are Citizens, as defined herein, (iv) of which not less
          than 75% of the

                                       4
 

<PAGE>   5

          voting power is vested in Citizens, as defined herein, free and clear
          of any trust or fiduciary obligation in favor of any Non-Citizens, as
          defined herein, and (v) of which more than 50% of that number of its
          directors (or equivalent Persons) necessary to constitute a quorum
          are Citizens, as defined herein;

                    (6)  any joint venture (if not an association, corporation,
          partnership or limited liability company) (i) that is organized under
          the laws of the United States or of a state, territory, district or
          possession thereof, and (ii) of which 100% of the equity is
          Beneficially Owned by and vested in Citizens, as defined herein, free
          and clear of any trust or fiduciary obligation in favor of any
          Non-Citizens, as defined herein;

                    (7)  any trust (i) that is domiciled in and existing under
          the laws of the United States or a state, territory, district or
          possession thereof, (ii) the trustee of which is a Citizen, as
          defined herein, and (iii) of which not less than 75% interest is held
          for the benefit of Citizens, as defined herein, free and clear of any
          trust or fiduciary obligation in favor of any Non-Citizens, as
          defined herein; and

                    (8) any other entity not specifically listed in this
          Subsection that the Board of Directors reasonably determines is a
          "Citizen" consistent with the provisions of this Article and the
          Maritime Laws (as hereinafter defined).

               (c)  "Fair Market Value" shall mean the average Market Price of
one share of stock for the 30 consecutive trading days immediately preceding
the date of determination. The "Market Price" for a particular day shall mean:
(1) if the stock is quoted on the National Association of Securities Dealers,
Inc. Automated Quotation ("Nasdaq") National Market, the last reported sales
price, regular way, or, in case no sale takes place on such day, the average of
the reported closing bid and asked prices, regular way, as such prices are
reported on the Nasdaq National Market; and (2) if the stock is then listed or
admitted to unlisted trading privileges on a national securities exchange (then
registered as such pursuant to Section 6 of the Securities Exchange Act of
1934, as amended), as such prices referred to in clause (1) above are reported
on such exchange; and (3) if the stock is not then listed or admitted to
unlisted trading privileges on any national securities exchange, and is not
then included for quotation through the Nasdaq National Market, (i) the average
of the closing "bid" and "asked" prices on such day in the over-the-counter
market as reported by Nasdaq, or (ii) if "bid" and "asked" prices for the stock
on such day shall not have been reported on Nasdaq, the average of the "bid"
and "asked" prices for such day as furnished by any Nasdaq member firm
regularly making a market in and for the stock. If the stock ceases to be
publicly traded, the Fair Market Value thereof shall mean the fair value of one
share of stock determined in good faith by the Board of Directors of the
Corporation.

                  (d) "Maritime Laws" shall mean the Merchant Marine Act of
1936, as amended, the Shipping Act, 1916, as amended and the regulations
promulgated thereunder (including

                                       5
<PAGE>   6

regulations relating to the citizenship of vessel owners), as such laws and
regulations shall be amended from time to time.

                    (e)  "Non-Citizen" shall mean any Person other than a
Citizen.

                    (f)  "Permitted Percentage" shall mean 24.99%

                    (g)  "Person" shall mean any individual, corporation,
trust, partnership, joint venture, association, joint-stock company,
unincorporated organization, government or any agency or political subdivision
thereof or any other entity.

         5.2 GENERAL POLICY. It is the policy of the Corporation that
Non-Citizens should Beneficially Own, individually or in the aggregate, no more
than the Permitted Percentage of the capital stock of the Corporation and no
more than the Permitted Percentage of the voting power of the Corporation. If
at any time Non-Citizens, individually or in the aggregate, become the
Beneficial Owners of more than the Permitted Percentage of the capital stock of
the Corporation or more than the Permitted Percentage of the voting power of
the Corporation, then the Corporation shall have the power to take the actions
prescribed in this Article . The provisions of this Article are intended to
assure that the Corporation remains in continuous compliance with the
citizenship requirements of the Maritime Laws. The Board of Directors (or any
duly constituted committee thereof) is specifically authorized to make all such
reasonable determinations and interpretations of terms used in this Article to
assure compliance with the Maritime Laws in accordance with applicable law and
this Certificate of Incorporation to take such other actions or make such
interpretations of this Certificate of Incorporation as it may deem necessary
or advisable in order to implement the policy set forth in this Section .

         5.3 DUAL STOCK CERTIFICATE SYSTEM. To implement the policy set forth
in Section , the Corporation shall institute a Dual Stock Certificate System
such that (a) each stock certificate representing shares of a class of series
of its capital stock that are Beneficially Owned by a Citizen shall be marked
"Citizen" and each stock certificate representing shares of such class or
series of capital stock that are Beneficially Owned by a Non-Citizen shall be
marked "Non-Citizen," but with all such stock certificates to be identical in
all other respects and to comply with all provisions of the laws of the State
of Delaware; (b) to the extent necessary to enable the Corporation to submit
any proof of citizenship required by law or by contract with the United States
government (or any agency thereof), the Corporation may require the record
holders and the Beneficial Owners of its capital stock to confirm their
citizenship status from time to time, and dividends payable with respect to
stock held by such record holder or owned by such Beneficial Owner may, in the
discretion of the Board of Directors, be withheld until confirmation of such
citizenship status is received; and (c) the stock transfer records of the
Corporation shall be maintained in such manner as to enable the percentage of a
class or series of its capital stock that is Beneficially Owned by Non-Citizens
and by Citizens to be confirmed.

                                       6
 

<PAGE>   7

          Nothing contained in this Certificate of Incorporation shall be
construed as requiring the Corporation to issue physical certificates in
connection with the issuance of shares of its stock held through The Depository
Trust Company or other depository if the Board of Directors determines that The
Depository Trust Company or such other depository has established procedures
that will allow the Corporation to determine the citizenship of the Beneficial
Owner of shares of its stock held through them. The Board of Directors is
authorized to take such actions or make such interpretations of this
Certificate of Incorporation as it may deem necessary or advisable in order to
facilitate the trading of capital stock through The Depository Trust Company or
other depository as the Board of Directors may determine.

         5.4 RESTRICTIONS ON TRANSFER. Any transfer, or attempted transfer, of
any shares of the Corporation's capital stock, the effect of which would be to
cause one or more Non-Citizens to Beneficially Own capital stock in excess of
the Permitted Percentage, or to have more than the Permitted Percentage of the
voting power of the Corporation, shall be ineffective as against the
Corporation, and neither the Corporation nor its transfer agent shall register
such transfer or purported transfer on the stock transfer records of the
Corporation and neither the Corporation nor its transfer agent shall be
required to recognize the transferee or purported transferee thereof as a
stockholder of the Corporation for any purpose whatsoever except to the extent
necessary to effect any remedy available to the Corporation under this Article
5. A citizenship certificate shall be required (unless waived by the
Corporation) from all transferees (and from any recipient upon original
issuance) of stock certificates representing shares of capital stock of the
Corporation and, if such transferee (or recipient) is acting as a fiduciary or
nominee for a Beneficial Owner, with respect to such Beneficial Owner, and
registration of transfer (or original issuance) shall be denied upon refusal to
furnish such certificate.

         5.5 NO VOTING RIGHTS, TEMPORARY WITHHOLDING OF DIVIDENDS AND OTHER
DISTRIBUTIONS. If on any date (including any record date) the number of shares
of capital stock of the Corporation that is Beneficially Owned by Non-Citizens
(i) is in excess of the Permitted Percentage of capital stock of the
Corporation or (ii) confers on Non-Citizens more than the Permitted Percentage
of the voting power of the Corporation (such shares herein referred to as the
"Excess Shares"), the Corporation shall determine those shares Beneficially
Owned by Non-Citizens that constitute such Excess Shares. The determination of
those shares that constitute Excess Shares shall be made by reference to the
date or dates Beneficial Ownership of such shares was acquired by Non-Citizens,
starting with the most recent acquisition of Beneficial Ownership of shares of
capital stock by a Non-Citizen and including, in reverse chronological order of
acquisition, all other acquisitions of shares of capital stock by Non-Citizens
from and after the acquisition of Beneficial Ownership of those shares of
capital stock by a Non-Citizen that first caused the Permitted Percentage to be
exceeded. If the number of shares acquired by Non-Citizens on any day on which
Excess Shares are so determined to be acquired exceed the number of shares
which are Excess Shares, the Excess Shares shall be prorated among all
acquisitions acquired by Non-Citizens on such date. For the purposes of this
Article 5, Excess Shares that result from a determination that a stockholder is
no longer a Citizen will be deemed to have been acquired as of the date that it
is determined that such

                                       7
<PAGE>   8

stockholder ceases to be a Citizen. The determination of the Corporation as to
those shares that constitute the Excess Shares shall be conclusive. Shares
deemed to constitute such Excess Shares shall (so long as such excess exists)
not be accorded any voting rights and shall not be deemed to be outstanding for
purposes of determining the vote required on any matter properly brought before
the stockholders of the Corporation for a vote thereon. The Corporation shall
(so long as such excess exists) withhold the payment of dividends and the
sharing in any other distribution (upon liquidation or otherwise) in respect of
the Excess Shares. At such time as the Permitted Percentage is no longer
exceeded, full voting rights shall be restored to any shares previously deemed
to be Excess Shares and any dividend or distribution with respect thereto that
has been withheld shall be due and paid solely to the record holders of such
shares at the time the Permitted Percentage is no longer exceeded.

          5.6  REDEMPTION OF EXCESS SHARES. Unless such redemption is not
permitted under Section 170 of the GCL or under other provisions of applicable
law, Excess Shares shall be subject to redemption by the Corporation (by action
of the Board of Directors, in its discretion) solely to the extent necessary to
reduce the aggregate number of shares of such capital stock owned by
Non-Citizens to the Permitted Percentage. The terms and conditions of such
redemption shall be as follows:

               (a)  the per share redemption (the "Redemption Price") to be
paid for the Excess Shares shall be the sum of (1) the Fair Market Value (on
the Transfer Date) of such shares of capital stock plus (2) an amount equal to
the amount of any dividend or any other distribution (upon a liquidation or
otherwise) declared in respect of such shares prior to the date on which such
shares are called for redemption and which amount has been withheld by the
Corporation pursuant to Section .

               (b)  the Redemption Price shall be paid in cash (by bank or
cashier's check);

               (c)  the Excess Shares to be redeemed shall be selected in the
same manner as provided in Section and shall not exceed the number necessary to
reduce the percentage of shares of capital stock owned by Non-Citizens, in the
aggregate, to the Permitted Percentage; provided that the Corporation may
adjust upward to the nearest whole share the number of shares to be redeemed so
as not to be required to redeem or require the sale of fractional shares;

               (d)  written notice of the date of redemption (the "Transfer
Date") together with a letter of transmittal to accompany certificates
representing shares of stock that are surrendered for redemption (if any) shall
be given either by hand delivery or by overnight courier service or by
first-class mail, postage prepaid, to each holder of record of the selected
shares to be redeemed, at such holder's last known address as the same appears
on the stock register of the Corporation (unless such notice is waived in
writing by any such holders) (the "Transfer Notice");

                                       8
<PAGE>   9

               (e)  the Transfer Date (for purposes of determining right, title
and interest in and to shares of capital stock being selected for redemption)
shall be the later of (1) the date specified in the Transfer Notice furnished
to record holders (which shall not be earlier than the date of such notice) or
(2) in the case of a redemption, the date on which the funds necessary to
effect the redemption have been irrevocably deposited in trust for the benefit
of such record holders;

               (f)  each Transfer Notice shall specify (1) the Transfer Date
(as determined pursuant to Subsection ); (2) the number of shares of capital
stock to be redeemed from such holder (and, to the extent such shares are
certificated, the certificate number(s) representing such shares); (3) the fact
that all right, title and interest in respect of the shares so selected for
redemption shall cease and terminate on the Transfer Date, except for the right
to receive the Redemption Price plus any dividend or distribution with respect
to such shares held pursuant to Section without interest; (4) the Redemption
Price and the manner of payment thereof; (5) the place where certificates for
such shares (if such shares are certificated) are to be surrendered for
cancellation against the simultaneous payment of the Redemption Price; and (6)
any instructions as to the endorsement or assignment for transfer for such
certificates (if any) and the completion of the accompanying letter of
transmittal;

               (g)  from and after the Transfer Date, all right, title and
interest in respect of the shares selected for redemption shall cease and
terminate, such shares shall no longer be deemed to be outstanding (and may
either be retired or held by the Corporation as treasury stock) and the owners
of such shares shall thereafter be entitled only to receive the Redemption
Price;

               (h)  upon surrender of the certificates (if any) for any shares
so redeemed in accordance with the requirements of the Transfer Notice and
accompanying letter of transmittal (and otherwise in proper form for transfer
as specified in the Transfer Notice), the owner of such shares shall be
entitled to payment of the Redemption Price. In case fewer than all the shares
represented by any such certificate are redeemed, a new certificate (or
certificates), to the extent such shares were certificated, shall be issued
representing the shares not redeemed without cost to the holder thereto; and

               (j)  In the event the Corporation is not permitted by applicable
law to make such redemption or the Board of Directors, in its discretion,
elects not to make such redemption, then the Corporation may direct the holder
of Excess Shares to sell all such Excess Shares for cash in such manner as the
Board of Directors directs.

          5.7  DETERMINATION OF CITIZENSHIP. In determining the citizenship of
the Beneficial Owners or their transferees of its capital stock, the
Corporation may rely on the stock transfer records of the Corporation and the
citizenship certificates given by Beneficial Owners or their transferees or any
recipients (in the case of original issuance) (in each case whether such
certificates have been given on their own behalf or on behalf of others) to
prove the citizenship of such Beneficial Owners, transferees or recipients of
such capital stock. The determination of

                                       9
 

<PAGE>   10
the citizenship of Beneficial Owners and their transferees of the capital stock
may also be subject to proof in such other way or ways as the Corporation may
deem reasonable. The Corporation may at any time reasonably require proof, in
addition to the citizenship certificates, of the Beneficial Owner or proposed
transferee of its capital stock and of such person's citizenship, and the
payment of dividends may be withheld, and any application for transfer of
ownership on the stock transfer records of the Corporation may be refused,
until such additional proof is submitted.

          5.8  SEVERABILITY. Each provision of this Article is intended to be
severable from every other provision. If any one or more of the provisions
contained in this Article is held to be invalid, illegal or unenforceable, the
validity, legality or enforceability of any other provision of this Article
shall not be affected, and this Article shall be construed as if the provisions
held to be invalid, illegal or unenforceable had never been contained herein.

          5.9  EXCEPTIONS. The Board of Directors may, upon receipt of either
an appropriate ruling of the regulatory body with the responsibility for
interpreting and enforcing the Maritime Laws, an opinion of counsel
satisfactory to the Board of Directors or such other evidence as the Board of
Directors deems appropriate, but shall in no case be required to, exempt a
Person (the "Exempted Holder") from classification as a "Non-Citizen", if the
Board of Directors determines that doing so would not cause the Corporation to
cease to be in continuous compliance with the citizenship requirements of the
Maritime Laws. The Board of Directors may condition its granting of a waiver on
the Exempted Holder's agreeing to such terms and conditions as the Board of
Directors determines to be appropriate in the circumstances.

          5.10 TERMINATION OF ARTICLE 5 RESTRICTIONS. The Board of Directors
may revoke all or any of the restrictions on transfer contained in this Article
5 if, in its discretion, compliance with the citizenship requirements of the
Maritime Laws, or any restriction contained in this Article 5, is no longer in
the best interests of the Corporation.

          5.11 EXCHANGE TRANSACTIONS. If the Corporation's capital stock is
listed or admitted to unlisted trading privileges on a national securities
exchange, nothing in this Article shall preclude the settlement of any
transaction entered into through the facilities of such exchange.

                                   ARTICLE 6

         A director of this Corporation shall not be personally liable to the
Corporation or its stockholders for monetary damages for breach of fiduciary
duty as a director, provided however, that the foregoing clause shall not
eliminate or limit the liability of a director (i) for any breach of the
director's duty of loyalty to the Corporation or its stockholders, (ii) for
acts or omissions not in good faith or which involve intentional misconduct or
a knowing violation of the law, (iii) under Section 174 of the GCL, or (iv) for
any transaction from which the director derived an improper personal benefit.
If the GCL is amended to authorize corporate action further eliminating or
limiting the personal liability of directors, then the liability of a director
of the 

                                      10


                                                                               

<PAGE>   11
Corporation shall be eliminated or limited to the fullest extent permitted by
the GCL. Any repeal or modification of the foregoing provision by the
stockholders of the Corporation shall not adversely affect any right or
protection of any director of the Corporation for or with respect to any action
or omission of such person occurring prior to such repeal or modification.

                                  ARTICLE 7

         The Corporation may, but shall not be obligated to, indemnify to the
fullest extent permitted by law any person made or threatened to be made a
party to an action or proceeding, whether criminal, civil, administrative or
investigative, including without limitation actions or proceedings by or in the
right of the Corporation, by reason of the fact that the person, his or her
testator or intestate is or was a director, officer or employee of the
Corporation or any predecessor of the Corporation or serves or served any other
enterprise as a director, officer or employee at the request of the Corporation
or any predecessor of the Corporation. The rights to indemnification granted
hereunder shall not be deemed exclusive of any other rights to indemnification
or the advancement of expenses which a director, officer or employee may be
entitled under any written agreement, Board of Directors' resolution, vote of
stockholders or otherwise. The Corporation may, but shall not be required to,
supplement the foregoing rights to indemnification by the purchase of insurance
on behalf of any one or more of its directors or officers. The provisions of
this Article are intended solely for the benefit of the indemnified parties
described herein, their heirs and personal representatives and shall not create
any rights in favor of third parties.

                                   ARTICLE 8

         The address of the registered office of the Corporation in the state
of Delaware, and the name of the registered agent at that address, are:

                           The Prentice-Hall Corporation System, Inc.
                           1013 Centre Road
                           Wilmington, Delaware
                           County of New Castle

                                      11
                                                                             
<PAGE>   12

                                   ARTICLE 9

         In furtherance and not in limitation of the powers conferred by
statute, the Board of Directors is expressly authorized to adopt, amend or
repeal, change or add to, the Bylaws of the Corporation without the assent or
vote of the stockholders.

                                   ARTICLE 10

         Elections of directors need not be by written ballot unless the Bylaws
of the Corporation shall so provide. The books of the Corporation may be kept
(subject to any provision contained in the GCL) outside the state of Delaware
at such place or places as may be designated from time to time by the Board of
Directors or in the Bylaws of the Corporation.

                                   ARTICLE 11

         The Corporation reserves the right to amend, alter, change or repeal
any provision contained in this Amended and Restated Certificate of
Incorporation, in the manner now or hereafter prescribed by statute, and all
rights conferred upon stockholders herein are granted subject to this
reservation.

                                 * * * * * * *

         I, THE UNDERSIGNED, being the Chairman and Chief Executive Officer of
the Corporation, do make this certificate, hereby declaring and certifying that
this act and deed and the facts herein stated are true, and accordingly have
hereunto set my hand this ____ day of ____________, 1997.




                                           ------------------------------------ 
                                           JOHN D. McCOWN
                                           Chairman and Chief Executive Officer

STATE OF ________________
COUNTY OF ________________

         The foregoing instrument was acknowledged before me this ___ day of
_________, 1997, by John D. McCown, Chairman and Chief Executive Officer of
Trailer Bridge, Inc., a Delaware corporation, on behalf of the corporation. He
is personally known to me or has produced ________________
_________________________ as identification.

                                      12

<PAGE>   13

{Notary Seal must be affixed}

                                      ------------------------------------------
                                      Signature of Notary

                                      ------------------------------------------
                                      Name of Notary (Typed, Printed or Stamped)

                                      Commission Number (if not legible
                                      on seal):
                                               ---------------------------------

                                      My Commission Expires (if not
                                      legible on seal):
                                                       -------------------------



                                       13


                             

<PAGE>   1
                                                              EXHIBIT 3.2



                                     BYLAWS
                                       OF
                              TRAILER BRIDGE, INC.
                            (a Delaware corporation)

                               ARTICLE I. OFFICES

                  1.01. Principal and Business Offices. The Corporation may
have such principal and other business offices, either within or without the
State of Delaware, as the Board of Directors may designate or as the business
of the Corporation may require from time to time.

                  1.02. Registered Office. The registered office of the
Corporation required by the General Corporation Law of the state of Delaware
(the "GCL") to be maintained in the State of Delaware may be, but need not be,
identical with the principal office in the State of Delaware, and the address
of the registered office may be changed from time to time by the Board of
Directors or by the registered agent. The business office of the registered
agent of the Corporation shall be identical to such registered office.

                            ARTICLE II. STOCKHOLDERS

                  2.01. Annual Meeting. The annual meeting of the stockholders
shall be held at such places, within or without the state of Delaware, and at
such times and dates as shall be designated by the Chairman of the Board of
Directors and stated in the notice of such meetings for the purposes of
electing directors and for the transaction of such other business as may come
before the meeting.

                  2.02. Special Meetings. Special meetings of the stockholders,
for any purpose or purposes, unless otherwise prescribed by statute, may be
called by the Chairman of the Board, and shall be called by the Chairman of the
Board or Secretary at the request in writing of a majority of the entire Board
of Directors, or by such other officer expressly designated by the Board of
Directors to call such meeting. Such request shall state the purpose or
purposes of the proposed meeting. Business transacted at all special meetings
shall be confined to the objects stated in the notice of the meeting. Special
meetings shall be held at such place, within or without the state of Delaware,
and at such time and date as shall be designated by the Chairman of the Board
of Directors and stated in the notice.

                  2.03. Notice of Meeting. Whenever stockholders are required
or permitted to take any action at a meeting, a written notice stating the
place, date and hour of the meeting of stockholders and, in case of a special
meeting, the purpose or purposes for which the meeting is called. Unless
otherwise provided by the GCL, the written notice of any meeting shall be given
not less than ten (10) days nor more than sixty (60) days before the date of
the meeting to each stockholder entitled to vote at such meeting. If mailed,
such notice shall be deemed to be given when deposited in the United States
mail, postage prepaid, directed to the stockholder at his address as it appears
on the records of the Corporation. [Any previously scheduled meeting of the
stockholders may be postponed by resolution of the Board of

<PAGE>   2
Directors upon public notice given prior to the date previously scheduled for
such meeting of stockholders.]

                  2.04. Adjournment. Any meeting of stockholders may be
adjourned to another time and place by vote of a majority of the shares
represented thereat. When so adjourned, notice need not be given of the
adjourned meeting if the time and place thereof are announced at the meeting at
which the adjournment is taken, unless the adjournment is for more than thirty
(30) days or a new record date is fixed for the adjourned meeting, in which
case notice of the adjourned meeting shall be given to each stockholder of
record entitled to vote at the meeting. Unless a new record date for the
adjourned meeting is fixed, the determination of stockholders of record
entitled to notice or to vote at the meeting at which adjournment is taken
shall apply to the adjourned meeting. At the adjourned meeting, the Corporation
may transact any business which might have been transacted at the original
meeting.

                  2.05. Fixing of Record Date. In order that the Corporation
may determine the stockholders entitled to notice of or to vote at any meeting
of stockholders or any adjournment thereof, or stockholders entitled to receive
payment of any dividend, or in order to make a determination of stockholders
for any other proper purpose, the Board of Directors may fix a record date,
which record date shall not precede the date upon which the resolution fixing
the record date is adopted by the Board of Directors, and which record date
shall not

                  (a) in the case of determination of stockholders entitled to
         vote at any meeting of stockholders or any adjournment thereof, shall
         not be more than sixty (60) days, nor less than ten (10) days prior to
         the date of such meeting;

                  (b) in the case of determination of stockholders entitled to
         express consent to corporate action in writing without a meeting,
         shall not be more than ten days from the date upon which the
         resolution fixing the record date is adopted by the Board of
         Directors;

                  (c) in the case of any other action, shall not be more than
         sixty days prior to such other action.

If no record date is fixed, the record date for determining:

                  (a) stockholders entitled to notice of or to vote at a
         meeting of stockholders shall be at the close of business on the day
         next preceding the day on which notice is given, or, if notice is
         waived, at the close of business on the day next preceding the day on
         which the meeting is held;

                  (b) stockholders entitled to express consent to a corporate
         action in writing without a meeting when no prior action of the Board
         of Directors is required by the GCL, shall be the first date on which
         a signed written consent setting forth the action taken or proposed to
         be taken is delivered to the Corporation in accordance with applicable
         law, or, if prior action by the Board of Directors is required by the
         GCL, shall be at the close of business on the day on which the Board
         of Directors adopts the resolution taking such prior action; or

<PAGE>   3

                  (c) stockholders for any other purpose shall be the close of
         business on the day on which the Board of Directors adopts the
         resolution relating thereto.

A determination of stockholders of record entitled to notice of or to vote at a
meeting of stockholders shall apply to any adjournment of the meeting;
provided, however, that the Board of Directors may fix a new record date for
the adjourned meeting.

                  2.06. Voting Records. The officer who has charge of the stock
ledger of the Corporation shall, at least ten (10) days before every meeting of
stockholders, prepare and make a complete list of the stockholders entitled to
vote at the meeting, arranged in alphabetical order, and showing the address of
each stockholder and the number of shares registered in the name of each
stockholder. Such list shall be open to the examination of any stockholder, for
any purpose germane to the meeting, during ordinary business hours, for a
period of at least ten (10) days prior to the meeting, either at a place within
the city where the meeting is to be held, which place shall be specified in the
notice of the meeting, or, if not so specified, at the place where the meeting
is to be held. The list shall also be produced and kept at the time and place
of the meeting during the whole time thereof, and may be inspected by any
stockholder who is present. Upon the wilful neglect or refusal of the directors
to produce such a list at any meeting for the election of directors, they shall
be ineligible for election to any office at such meeting. The stock ledger
shall be the only evidence as to who are the stockholders entitled to examine
the stock ledger, the list of stockholders, or to vote in person or by proxy at
any meeting of stockholders.

                  2.07. Quorum. Except as otherwise provided by the GCL, in the
Certificate of Incorporation or in these Bylaws, a majority of the shares
entitled to vote, present in person or represented by proxy, shall constitute a
quorum at a meeting of stockholders, but in no event shall a quorum consist of
less than one-third of the shares entitled to vote at the meeting. In the
absence of a quorum, the stockholders so present may, by majority vote, adjourn
the meeting from time to time in the manner provided in Section 2.04 of these
Bylaws until a quorum shall attend. Shares of its own stock belonging to the
Corporation or to another corporation, if a majority of the shares entitled to
vote in the election of directors of such other corporation is held, directly
or indirectly, by the Corporation, shall neither be entitled to vote not be
counted for quorum purposes; provided, however that the foregoing shall not
limit the right of the Corporation to vote stock, including but not limited to
its own stock, held by it in a fiduciary capacity.

                  2.08. Conduct of Meeting. The Chairman of the Board of
Directors, and in his absence, the Vice Chairman of the Board of Directors, or
in their absence, any person chosen by the stockholders present shall call the
meeting of the stockholders to order and shall act as chairman of the meeting.
The Secretary of the Corporation shall act as secretary of all meetings of the
stockholders, but, in the absence of the Secretary, the presiding officer amy
appoint any other person to act as secretary of the meeting. The Board of
Directors of the Corporation may adopt by resolution such rules and regulations
for the conduct of the meeting of stockholders as it shall deem appropriate.
Except to the extent inconsistent with such rules and regulations as adopted by
the Board of Directors, the chairman of any meeting of stockholders shall have
the right and authority to prescribe such rules, regulations and procedures and
to do all such acts as, in the judgment of such chairman, are appropriate for
the proper conduct of such meeting. Such rules, regulations or procedures,
whether adopted by the Board of Directors or prescribed by the chairman of the
meeting, may include, without

<PAGE>   4

limitation, the following: (a) the establishment of an agenda or order of
business for the meeting; (b) rules and procedures for maintaining order at the
meeting and the safety of those present; (c) limitations on attendance at or
participation in the meeting to stockholders of records of the Corporation,
their duly authorized and constituted proxies or such other persons as the
chairman of the meeting shall determine; (d) restrictions on entry to the
meeting after the time fixed for the commencement thereof; and (e) limitations
on the time allotted to questions or comments by participants. Unless and to
the extent determined by the Board of Directors or the chairman of the meeting,
meetings of stockholders shall not be required to be held in accordance with
the rules of parliamentary procedure.

                  2.09. Proxies. Except as otherwise provided by the
Certificate of Incorporation, each a stockholder entitled to vote at any
meeting of stockholders or to express consent or dissent to corporate action in
writing without a meeting may authorize another person or persons to act for
him by proxy, but no such proxy shall be voted or acted upon after three years
from its date, unless the proxy provides for a longer period. A proxy shall be
irrevocable if it states that it is irrevocable and if, and only as long as, it
is coupled with an interest sufficient in law to which is not irrevocable
power. A stockholder may revoke any proxy which is not irrevocable by attending
the meeting and voting in person or by filing an instrument in writing revoking
the proxy or by delivering a proxy in accordance with applicable law bearing a
later date to the Secretary of the Corporation.

                  2.10. Voting of Shares. Unless otherwise provided in the
Certificate of Incorporation, each stockholder entitled to vote at any meeting
of stockholders shall be entitled to one vote for each share of stock held by
him which has voting power upon the matter in question. Voting at meetings of
stockholders need not be by written ballot and, unless otherwise required by
law, need not be conducted by the inspector of election unless so determined by
the holders of shares of stock having a majority of the votes which could be
cast by the holders of all outstanding shares of stock entitled to vote thereon
which are present in person or by proxy at such meeting. At all meetings of
stockholders for the election of directors a plurality of the votes cast shall
be sufficient to elect. All other elections and questions shall, unless
otherwise provided by law, the Certificate of Incorporation or these Bylaws, be
decided by the vote of the holders of shares of stock having a majority of the
votes which could be cast by the holders of all shares of stock outstanding and
entitled to vote thereon.

                  2.11. Stockholders Consent Without Meeting. Unless otherwise
provided in the Certificate of Incorporation, any action required by the GCL to
be taken at any annual or special meeting of the stockholders of the
Corporation, or any action which may be taken at any annual or special meeting
of such stockholders, may be taken without a meeting, without prior notice and
without a vote, if a consent or consents in writing, setting forth the action
so taken, shall be signed by the holders of outstanding stock having not less
than the minimum number of votes that would be necessary to authorize or take
such action at a meeting at which all shares entitled to vote thereon were
present and voted and shall be delivered to the Corporation by delivery to its
registered office in this State, its principal place of business or an officer
or agent of the Corporation having custody of the book in which proceedings of
meetings of stockholders are recorded. Delivery made to the Corporation's
registered office shall be by hand or by certified or registered mail, return
receipt requested. Prompt notice of the taking of the corporate action without
a meeting by less than unanimous written consent shall be given to those
stockholders who have not consented in writing and who, if the action

<PAGE>   5

had been taken at a meeting, would have been entitled to notice of the meeting
if the record date for such meeting had been the date that written consents
signed by a sufficient number of holders to take the action were delivered to
the Corporation as provided by applicable law.


                  2.12. Notice of Stockholder Business. At an annual meeting of
the stockholders, only such business shall be conducted as shall have been
properly brought before the meeting. To be properly brought before an annual
meeting, business must be (a) specified in the notice of meeting (or any
supplement thereto) given by or at the direction of the Board of Directors, (b)
otherwise properly brought before the meeting by or at the direction of the
Board of Directors, or (c) otherwise properly brought before the meeting by a
stockholder. For business to be properly brought before an annual meeting by a
stockholder, the stockholder must have given timely notice thereof in writing
to the Secretary of the Corporation. To be timely, a stockholder's notice must
be delivered to or mailed and received at the principal executive offices of
the Corporation not less than sixty (60) days nor more than ninety (90) days
prior to meeting; provided, however, that in the event that less than seventy
(70) days' notice or prior public disclosure of the date of the meeting is
given or made to stockholders, notice by the stockholder to be timely must be
received no later than the close of business on the tenth day following the day
on which such notice of the date of the annual meeting was mailed or such
public disclosure was made. A stockholder's notice to the Secretary shall set
forth as to each matter the stockholder proposes to bring before the annual
meeting (a) a brief description of the business desired to be brought before
the annual meeting and the reasons for conducting such business at the annual
meeting, (b) the name and address, as they appear on the Company's books, of
the stockholder proposing such business, (c) the class and number of shares of
the Company which are beneficially owned by the stockholder, and (d) any
material interest of the stockholder in such business. Notwithstanding anything
in these Bylaws to the contrary, no business shall be conducted at an annual
meeting except in accordance with the procedures set forth in this Section
2.12. The Chairman of an annual meeting shall, if the facts warrant, determine
and declare to the meeting that business was not properly brought before the
meeting and in accordance with the provisions of this Section 2.12 and if he
should so determine, he shall so declare to the meeting and any such business
not properly brought before the meeting shall not be transacted.

                        ARTICLE III. BOARD OF DIRECTORS

                  3.01. General Powers and Number. The business and affairs of
the Corporation shall be managed by or under the direction of the Corporation's
Board of Directors, except as otherwise provided in the GCL or in the
Certificate of Incorporation. The Board of Directors shall consist of one or
more members, the number thereof to be determined from time to time by
resolution of the Board of Directors, unless otherwise provided in the
Certificate of Incorporation. Directors need not be stockholders.

                  3.02. Tenure. Each director shall hold office until the next
annual meeting of stockholders or until his successor is elected and qualified,
or until his earlier resignation or removal. Any director may resign at any
time upon written notice to the Corporation. Any director or the entire Board
of Directors may be removed, with or without cause, by the holders a majority
of the shares then entitled to vote at an election of such director.

<PAGE>   6

                  3.03. Regular Meetings. Regular meetings of the Board of
Directors may be held at such places within or without the State of Delaware
and at such times as the Board of Directors may from time to time determine,
and if so determined notices thereof need not be given.

                  3.04. Special Meetings. Special meetings of the Board of
Directors may be held at any time or place within or without the State of
Delaware whenever called by the Chairman of the Board, the Chief Executive
Officer or any two directors. The Chairman of the Board of Directors, the Chief
Executive Officer or the directors calling any special meeting of the Board of
Directors may fix any place, either within or without the State of Delaware, as
the place for holding any special meeting of the Board of Directors called by
them, and if no other place is fixed the place of the meeting shall be the
principal office of the Corporation.

                  3.05. Notice; Waiver. Notice of each meeting of the Board of
Directors (unless otherwise provided in or pursuant to Section 3.03) shall be
given to each director not less than twenty-four (24) hours prior to the
meeting by giving oral, telephone or written notice to a director in person, or
by facsimile transmission, or not less than three (3) days prior to a meeting
by delivering or mailing notice to the business address or such other address
as a director shall have designated in writing and filed with the Secretary. If
mailed, such notice shall be deemed to be delivered when deposited in the
United States mail so addressed, with postage thereon prepaid. If by facsimile
transmission, such notice shall be deemed adequately delivered when the notice
is transmitted at least 24 hours before such meeting.

                  3.06. Quorum. Except as otherwise provided by law or by the
Certificate of Incorporation or these Bylaws, a majority of the directors shall
constitute a quorum for the transaction of business at any meeting of the Board
of Directors, but in no event shall less than one-third of the directors
constitute a quorum, except that when the Board of Directors consists of one
(1) director, one (1) director shall constitute a quorum. A majority of the
directors present (though less than such quorum) may adjourn the meeting from
time to time without further notice. At such adjourned meeting at which a
quorum shall be present, any business may be transacted which might have been
transacted at the meeting as originally notified.

                  3.07. Manner of Acting. Except as otherwise required by the
Certificate of Incorporation or these Bylaws, the vote of a majority of the
directors present at a meeting at which a quorum is present shall be the act of
the Board of Directors.

                  3.08. Conduct of Meetings. The Chairman of the Board, if any,
and in his absence the Vice Chairman of the Board, if any, and in their
absence, any director chosen by the directors present, shall call meetings of
the Board of Directors to order and shall act as chairman of the meeting. The
Secretary of the Corporation shall act as secretary of all meetings of the
Board of Directors but in the absence of the Secretary, the presiding officer
may appoint any Assistant Secretary or any director or other person present to
act as secretary of the meeting.

                  3.09. Vacancies. Any newly created directorship or any
vacancy occurring in the Board of Directors for any cause may be filled by a
majority of the remaining members of the Board of Directors, although such
majority is less than a quorum, or by a sole remaining director, or by a
plurality of the votes cast at a meeting of stockholders, and each director so

<PAGE>   7

elected shall hold office until the expiration of the term of office of the
director whom he has replaced or until his successor is elected and qualified.

                   3.10. Nominations for Directors. Only persons who are
nominated in accordance with the provisions set forth in this Section 3.10
shall be eligible for election as Directors. Nominations of persons for
election to the Board of Directors of the Corporation at any meeting of
stockholders called for election of directors, in whole or in part (an
"Election Meeting"), may be made by the Board of Directors ("Board") or by any
stockholder entitled to vote at such Election Meeting who complies with the
notice provisions of this Section 3.10. Such notice, other than those made by
or at the direction of the Board of Directors, shall made pursuant to a timely
notice delivered to the Secretary of the Corporation setting forth (a) as to
each person whom the stockholder proposed to nominate for election or
re-election as a Director, (i) the name, age, business address and residence
address of each nominee proposed in such notice, (ii) the principal occupation
or employment of each such nominee, (iii) the class and number of shares of
capital stock of the Company which are beneficially owned by each such nominee
and (iv) such other information concerning each such nominee as would be
required, under the rules of the SEC, in a proxy statement soliciting proxies
for the election of such nominees, and (b) as to the stockholder giving the
notice (i) the name and address, as they appear on the Corporation's books, of
such stockholder and (ii) the class and number of shares of the Corporation
which are beneficially owned by such stockholder. Such notice shall include a
signed consent to serve as a director of the Company, if elected, of each such
nominee. To be timely, a stockholder's notice must be delivered to or mailed
and received at the principal executive offices of the Corporation no later
than not less than sixty (60) days nor more than ninety (90) days prior to the
meeting; provided, however, that in the event that less than seventy (70) days'
notice or prior public disclosure of the date of the meeting is given or made
to stockholders, notice by the stockholder to be timely must be received by the
Corporation not later than the close of business on the tenth day following the
date on which the Corporation mailed such notice or made a public disclosure.
No person shall be eligible for election as a Director of the Corporation
unless nominated in accordance with the procedures set forth in this Section
3.10. If the Chairman of the Election Meeting determines that a nomination was
not made in accordance with the foregoing procedures, the defective nomination
shall be void and disregarded.

                   3.11. Compensation. The Board of Directors, irrespective of
any personal interest of any of its members, may fix the compensation of all
directors for services to the Corporation as directors.

                   3.12. Committees. The Board of Directors by resolution
adopted by the affirmative vote of a majority of the directors may designate
one or more committees, each committee to consist of one or more members of the
Board of Directors The Board of Directors may designate one or more directors
as alternate members of any committee, who may replace any absent or
disqualified member at any meeting of the committee. In the absence or
disqualification of a member of the committee, the member or members thereof
present at any meeting and not disqualified from voting, whether or not he or
they constitute a quorum, may unanimously appoint another member of the Board
of Directors to act at the meeting in place of any such absent or disqualified
member. Any such committee, to the extent permitted by law and to the extent
provided in the resolution of the Board of Directors, shall have and may
exercise all the powers and authority of the Board of Directors in the
management of the business and affairs of the Corporation, and may authorize
the seal of the


<PAGE>   8

Corporation to be affixed to all papers which may require it. Unless the Board
of Directors otherwise provides, each committee designated by the Board of
Directors may make, alter and repeal rules for the conduct of its business. In
the absence of such rules each committee shall conduct its business in the same
manner as the Board of Directors conducts its business pursuant to these
Bylaws.

                  3.13. Unanimous Consent Without Meeting. Unless otherwise
restricted by the Certificate of Incorporation or these Bylaws, any action
required or permitted to be taken at a meeting of the Board of Directors, or by
any committee thereof, may be taken without a meeting if all members of the
Board of Directors or such committee, as the case may be, consent thereto in
writing, and the writing or writings are filed with the minutes of proceedings
of the Board of Directors or such committee.

                  3.14. Telephonic Meetings. Unless otherwise restricted by the
Certificate of Incorporation of these Bylaws, members of the Board of
Directors, or any committee designated by the Board, may participate in a
meeting of such Board or committee by means of conference telephone or similar
communications equipment by means of which all persons participating in the
meeting can hear each other, and participation in a meeting pursuant to this
Section 3.14 shall constitute presence in person at the meeting.

                              ARTICLE IV. OFFICERS

                  4.01. Officers; Election; Qualifications; Term of Office;
Resignation; Removal; Vacancies. The Board of Directors shall elect a President
and a Secretary of the Corporation. The Board of Directors may, if it so
determines, choose a Chairman of the Board and a Vice Chairman of the Board
from among its members. The Board of Directors also may choose one or more Vice
Presidents, one or more Assistant Secretaries, a Treasurer and one or more
Assistant Treasurers. Any number of offices may be held by the same person. The
authority of the Board to elect persons as certain officers of the Corporation
shall be subject to the requirements of Section 6.04 of these Bylaws.

                  4.02. Election and Term of Office. Subject to the provisions
of the Certificate of Incorporation and Section 6.04 of these Bylaws, each
officer of the Corporation shall hold office until the first meeting of the
Board of Directors after the annual meeting of stockholders next succeeding his
election, and until his successor is elected and qualified or until his earlier
resignation or removal. Any officer may resign at any time upon written notice
to the Corporation. Failure to elect officers shall not dissolve or otherwise
affect the Corporation.

                  4.03. Removal. The Board of Directors may remove any officer
with or without cause at any time, but such removal shall be without prejudice
to the contractual rights of

such officer, if any, with the Corporation.

                  4.04. Vacancies. A vacancy occurring in any office of the
Corporation by death, resignation, removal, disqualification or otherwise, may
be filled for the unexpired portion of the term by the Board of Directors,
subject to the requirements of Section 6.04 of these Bylaws, at any regular or
special meeting.

<PAGE>   9

                  4.05. Powers and Duties of Officers. The officers of the
Corporation shall have such powers and duties in the management of the
Corporation as may be prescribed in a resolution by the Board of Directors and,
to the extent not so provided, as generally pertain to their respective
offices, subject to the control of the Board of Directors. The Board of
Directors may require any officer, agent or employee to give security for the
faithful performance of his duties.

             ARTICLE V. CERTIFICATES FOR SHARES AND THEIR TRANSFER

                  5.01. Certificates for Shares. The shares of the Corporation
shall be represented by certificates, provided that the Board of Directors may
provide by resolution or resolutions that some or all of any classes or series
of its stock shall be uncertificated shares. Any such resolution shall not
apply to shares represented by a certificate until such certificate is
surrendered to the Corporation. Notwithstanding the adoption of any such
resolution, every holder of stock represented by certificates and upon request
every holder of uncertificated shares shall be entitled to have a certificate
signed by, or in the name of the Corporation by the Chairman or Vice-Chairman
of the Board of Directors, or President or a Vice President, and by the
Treasurer or an assistant Treasurer, or the Secretary or an Assistant Secretary
of the Corporation representing the number of shares registered in certificate
form.

                  5.02. Facsimile Signatures. Any or all of the signatures on
the certificate may be a facsimile.

                  5.03. Signature by Former Officers. In case any officer,
transfer agent or registrar who has signed or whose facsimile signature has
been placed upon any certificate, shall have ceased to be such officer,
transfer agent or registrar before such certificate is issued, it may be issued
by the Corporation with the same effect as if he or she were such officer,
transfer agent or registrar at the date of issue.

                  5.04. Lost, Destroyed or Stolen Certificates. The Corporation
may a new certificate of stock or uncertificated shares in place of any
certificate theretofore issued by it, alleged to have been lost, stolen or
destroyed, and the Corporation may require the owner of the lost, stolen or
destroyed certificate, or his legal representative to give the Corporation a
bond sufficient to indemnify it against any claim that may be made against the
Corporation on account of the alleged loss, theft or destruction of any such
certificate or the issuance of such new certificate or uncertificated shares.

                  5.05. Foreign Ownership Restrictions. The provisions of this
Article V shall be subject to the provisions of the Corporation's Certificate
of Incorporation.

                           ARTICLE VI. MISCELLANEOUS

                  6.01. Seal. The Board of Directors may, at their discretion,
provide a corporate seal in an appropriate form.

                  6.02. Fiscal Year. The fiscal year of the Corporation shall
begin on the first day of January and end on the thirty-first day of December
in each year.
<PAGE>   10

                  6.03. Waiver of Notice by Stockholders, Directors and
Committees. Whenever any notice is required to be given under the GCL or the
Certificate of Incorporation or these Bylaws, a written waiver, signed by the
person entitled to notice, whether before or after the time stated therein,
shall be deemed equivalent to notice. Attendance of a person at a meeting shall
constitute a waiver of notice of such meeting, except when the person attends a
meeting for the express purpose of objecting at the beginning of the meeting to
the transaction of any business because the meeting is not lawfully called or
convened. Neither the business to be transacted at, nor the purpose of, any
regular or special meeting of stockholders, directors or members of a committee
of directors need be specified in any written waiver of notice unless so
required by the Certificate of Incorporation of these Bylaws.

                  6.04. Citizenship of Directors and Officers. The Chairman of
the Board of Directors, the Chief Executive officer, the President, and the
Vice Presidents and any other persons who are authorized by the Board of
Directors to act in their absence, shall be citizens of the United States.
Other directors need not be citizens of the United States but the total number
of directors who are not citizens of the United States shall at no time exceed
a minority of the number necessary to constitute a quorum pursuant to Section
3.06 of these Bylaws.

                  6.05. Interested Directors; Quorum. No contract or
transaction between the Corporation and one or more of its directors or
officers, or between the Corporation and any other Corporation, partnership,
association, or other organization in which one or more of its directors or
officers are directors or officers, or have a financial interest, shall be void
or voidable solely because the director or officer is present at or
participates in the meeting of the Board of Directors or committee thereof
which authorizes the contract or transaction, or solely because his or their
votes are counted for such purpose, if: (i) the material facts as to his
relationship or interest and as to the contract or transaction are disclosed or
are known to the Board of Directors or the committee, and the Board of
Directors or committee in good faith authorizes the contract or transaction by
the affirmative votes of a majority of the disinterested directors, even though
the disinterested directors be less than a quorum; or (2) the material facts as
to his relationship or interest and as to the contract or transaction are
disclosed or are known to the stockholders entitled to vote thereon, and the
contract or transaction is specifically approved in good faith by vote of the
stockholders; or (3) the contract or transaction is fair as to the Corporation
as of the time it is authorized, approved or ratified, by the Board of
Directors, a committee thereof, or the stockholders, the Board of Directors, a
committee thereof, or the stockholders. Common or interested directors may be
counted in determining the presence of a quorum at a meeting of the Board of
Directors or of a committee which authorizes the contract or transaction.

                  6.06. Amendment. These Bylaws may be altered or repealed,
and new Bylaws made, by the Board of Directors as provided in the Certificate
of Incorporation, but the stockholders may make additional Bylaws and may alter
and repeal any Bylaws whether adopted by them or otherwise.



<PAGE>   1
                                                                 EXHIBIT 5


                         [FOLEY & LARDNER LETTERHEAD]


                                June 30, 1997



Trailer Bridge, Inc.
9550 Regency Square Boulevard, Suite 500
Jacksonville, Florida  32225

     Registration Statement on Form S-1
     Registration No. 333-28221

Gentlemen:

     This opinion is being furnished in connection with the Registration
Statement on Form S-1 (Registration No. 333-28221) of Trailer Bridge, Inc. (the
"Company"), under the Securities Act of 1933, as amended, for the registration
of shares of common stock, par value $0.01 (the "Shares").  The Registration
Statement filed May 30, 1997, as amended by Amendment No. 1 filed concurrently
herewith referred to herein as the "Registration Statement."

     As counsel for the Company, we have examined and are familiar with the
following:

     (a)  Certificate of Incorporation as filed in the Office of the Secretary
of State of the State of Delaware;

     (b)  Form of Amended and Restated Certificate of Incorporation of the
Company to be filed in the Office of the Secretary of State of the State of
Delaware;
 
     (c)  Form of Bylaws of the Company;

     (d)  The proceedings of the Board of Directors of the Company in
connection with or with respect to the issuance and sale of the Shares to be
sold by the Company to certain underwriters pursuant to an underwriting
agreement (the "Underwriting Agreement") between the Company and the
underwriters named in the Registration Statement; and

     (e)  Such other documents, Company records, and matters of law as we
deemed to be pertinent.


<PAGE>   2
     Based upon our examination of such documents and our familiarity with
such proceeds, it is our opinion that:

     1.   The Company has been duly incorporated and is validly existing and in
good standing under the laws of the State of Delaware.

     2.   Upon filing of the Amended and Restated Certificate of Incorporation
with the Office of the Secretary of State of the State of Delaware the Shares
covered by the Registration Statement (including the Shares covered by the
over-allotment described in the Registration Statement) to be sold by the
Company will, when the price therefor is approved by the board of directors of
the Company or the committee to which it has delegated pricing authority, and
when issued and delivered to the underwriters pursuant to the Underwriting
Agreement against payment of the consideration therefor specified therein, be
duly and validly issued, fully paid and nonassessable.

     We hereby consent to the inclusion of this opinion as Exhibit 5 in said
Registration Statement and to the reference to this firm under the caption
"Legal Matters" in the Prospectus.  In giving this consent we do not hereby
admit that we come within the category of persons whose consent is required
under Section 7 of the Securities Act of 1933, as amended, or the rules or
regulations of the Securities Exchange Commission promulgated thereunder.

                                            FOLEY & LARDNER



                                                                           

<PAGE>   1
                                                               Exhibit 10.4.3

                                      -1-





                                THIRD AMENDMENT
     TO CONSTRUCTION AND TERM LOAN AGREEMENT AND CONSENT AND LIMITED WAIVER


         Third Amendment dated as of January 1, 1997 to Construction and Term
Loan Agreement (the "Second Amendment"), by and among KADAMPANATTU CORP., a
Delaware corporation (the "Borrower"), TRAILER BRIDGE, INC., a Delaware
corporation (the "Guarantor"), THE FIRST NATIONAL BANK OF BOSTON and the other
lending institutions listed on Schedule 1 to the Credit Agreement (as
hereinafter defined) (the "Banks") and THE FIRST NATIONAL BANK OF BOSTON, as
agent for the Banks (in such capacity, the "Agent"), amending certain
provisions of the Construction and Term Loan Agreement dated as of October 13,
1995 (as amended and in effect from time to time, the "Credit Agreement") by
and among the Borrower, the Guarantor, the Banks and the Agent.  Terms not
otherwise defined herein which are defined in the Credit Agreement shall have
the same respective meanings herein as therein.

         WHEREAS, the Borrower, the Guarantor, the Banks and the Agent have
agreed to modify certain terms and conditions of the Credit Agreement as
specifically set forth in this Third Amendment;

         NOW, THEREFORE, in consideration of the premises and the mutual
agreements contained herein and for other good and valuable consideration, the
receipt and sufficiency of which are hereby acknowledged, the parties hereto
hereby agree as follows:

         Section 1.       AMENDMENT TO Section 10 OF THE CREDIT AGREEMENT.
Section 10 of the Credit Agreement is hereby amended by deleting Section 10.3
in its entirety and restating it as follows:

                 10.3.  LIABILITIES TO WORTH RATIO  The Borrower will not
         permit the ratio of Combined Total Liabilities to Combined Tangible
         Net Worth to exceed (a) 1.50:1.00 at any time from the Closing Date
         through December 31, 1996, (b) 1.75:1.00 at any time from January 1,
         1997 through December 31, 1997; (c) 1.50:1.00 at any time from January
         1, 1998 through December 31, 1998; and (d) 1.25:1.00 at any time
         thereafter.

         Section 2.       CONSENT AND LIMITED WAIVER.  Pursuant to the Security
Agreement, the Borrower is required to deliver to the Agent for the benefit of
the Agent and the Banks the proceeds of certain insurance proceeds received by
the Borrower, which proceeds shall be held by the Agent as cash collateral for
the Obligations and which cash collateral may be applied to the Obligations.
The Borrower has notified that Agent that it anticipates receiving
approximately $700,000 in insurance proceeds relating to a claim for damage to
one of the Vessels (the "Proceeds").  The Borrower has requested that the Agent





<PAGE>   2

                                      -2-




and the Banks waive this delivery requirement in connection with the Proceeds
and consent to the Borrower retaining such Proceeds.  The Agent and the Banks
hereby consent to waive such delivery requirement and consent to the Borrower
retaining the amount of the Proceeds.  The consent granted herein is limited
strictly to its terms, shall apply only to the specific transactions described
herein, shall not extend to or affect any of the Borrower's other obligations
contained in the Credit Agreement and the other Loan Documents and shall not
impair any rights consequent thereon.  The Agent and the Banks shall not have
any obligation to issue any further consent with respect to the subject matter
of this letter or any other matter..

         Section 3.       CONDITIONS TO EFFECTIVENESS.  This Third Amendment
shall not become effective until the Agent receives a counterpart of this Third
Amendment executed by the Borrower, the Guarantor, the Banks and the Agent.

         Section 4.       REPRESENTATIONS AND WARRANTIES.  Each of the Borrower
and the Guarantor hereby repeats, on and as of the date hereof, each of the
representations and warranties made by it in Section 7 of the Credit Agreement,
provided, that all references therein to the Credit Agreement shall refer to
such Credit Agreement as amended hereby.  In addition, each of the Borrower and
the Guarantor hereby represents and warrants that the execution and delivery by
the Borrower and the Guarantor of this Third Amendment and the performance by
the Borrower and the Guarantor of all of their agreements and obligations under
the Credit Agreement as amended hereby are within the corporate authority of
each of the Borrower and the Guarantor and have been duly authorized by all
necessary corporate action on the part of each of the Borrower and the
Guarantor.

         Section 5.       RATIFICATION, ETC.  Except as expressly amended
hereby, the Credit Agreement and all documents, instruments and agreements
related thereto, including, but not limited to the Security Documents, are
hereby ratified and confirmed in all respects and shall continue in full force
and effect.  The Credit Agreement and this Third Amendment shall be read and
construed as a single agreement.  All references in the Credit Agreement or any
related agreement or instrument to the Credit Agreement shall hereafter refer
to the Credit Agreement as amended hereby.

         Section 6.       NO WAIVER.  Except as expressly set forth in Section
2 above, nothing contained herein shall constitute a waiver of, impair or
otherwise affect any Obligations, any other obligation of the Borrower, the
Guarantor or any rights of the Agent or the Banks consequent thereon.

         Section 7.       COUNTERPARTS.  This Third Amendment may be executed
in one or more counterparts, each of which shall be deemed an original but
which together shall constitute one and the same instrument.

         Section 8.       GOVERNING LAW.  THIS THIRD AMENDMENT SHALL BE
GOVERNED BY, AND CONSTRUED IN ACCORDANCE WITH, THE LAWS OF THE COMMONWEALTH OF
MASSACHUSETTS (WITHOUT REFERENCE TO CONFLICT OF LAWS).

                  [REMAINDER OF PAGE INTENTIONALLY LEFT BLANK]





<PAGE>   3

                                      -3-




         IN WITNESS WHEREOF, the parties hereto have executed this Third
Amendment as a document under seal as of the date first above written.

                                  KADAMPANATTU CORP.
                                
                                
                                
                                  By:____________________________________
                                  Title:
                                
                                
                                  TRAILER BRIDGE, INC.
                                
                                
                                
                                  By:____________________________________
                                  Title:
                                
                                
                                  THE FIRST NATIONAL BANK OF BOSTON,
                                      individually and as Agent
                                
                                
                                
                                  By:____________________________________
                                  Title:
                                
                                
                                
                                  BANK ONE, LOUISIANA N.A.
                                
                                
                                
                                  By:_____________________________________
                                  Title:





<PAGE>   4





                            RATIFICATION OF GUARANTY

         The undersigned Guarantor hereby acknowledges and consents to the
foregoing Third Amendment as of January 1, 1997, and agrees that the Guaranty
dated as of October 13, 1995 (as amended and in effect from time to time) from
the Guarantor in favor of the Agent for the benefit of the Agent and the Banks
remains in full force and effect, and the Guarantor confirms and ratifies all
of its obligations thereunder.


                                                   TRAILER BRIDGE, INC.



                                                   By:_________________________
                                                   Title:






<PAGE>   1

                                                                EXHIBIT 10.8
                                                                          
                                                                Document 10.8

                                                          Contract No. MA-13304

                      COMMITMENT TO GUARANTEE OBLIGATIONS

                                       BY

                          THE UNITED STATES OF AMERICA

                                 UNDER TITLE XI

                  OF THE MERCHANT MARINE ACT, 1936, AS AMENDED

                                  ACCEPTED BY

                              TRAILER BRIDGE, INC.

                           Dated as of June 23, 1997


<PAGE>   2



                      COMMITMENT TO GUARANTEE OBLIGATIONS

                                       by

                          THE UNITED STATES OF AMERICA

                                  Accepted by

                              TRAILER BRIDGE, INC.
                                   Shipowner

                  (Under Title XI, Merchant Marine Act, 1936,
                        as amended, and in effect on the
                       date of this Guarantee Commitment)

                               TABLE OF CONTENTS
                               -----------------


<TABLE>
<CAPTION>
              Document
               Number               Document
               ------               --------
                  <S>    <C>
                  1      Commitment to Guarantee Obligations
                         Schedule One -- Form of Opinion of Counsel
                  2      Appendix I -- Form of Bond Purchase
                          Agreement
                  3      Appendix II -- Form of Trust Indenture
                  4      Schedule A -- Schedule of Definitions to
                                 Trust Indenture
                  5      Exhibit 1 -- General Provisions Incorporated
                         into the Trust Indenture by Reference
                  6      Exhibit 2 -- Forms of Bond, Guarantee and
                  7      Trustee's Authentication Certificate
                  7      Exhibit 3 -- Authorization Agreement
                  8      Exhibit 4 -- Form of Secretary's Supplemental
                                 Indenture
                  9      Appendix III -- Security Agreement
                  10     Exhibit 1 -- General Provisions Incorporated
                                 into the Security Agreement by Reference
                  11     Schedule X -- Schedule of Definitions
                  12     Exhibit 2 -- Form of Secretary's Note
                  13     Exhibit 3 -- Form of First Preferred
                         Mortgage
                  14     Exhibit 4 -- Title XI Reserve Fund and
                         Financial Agreement
</TABLE>

                                       i


<PAGE>   3




<TABLE>
                  <S>   <C>
                  15    Exhibit 5 -- General Provisions Incorporated
                                into the Title XI Reserve Fund and
                                Financial Agreement
                  16    Exhibit 6 -- Consent of Shipyards
                  17    Exhibit 7-- Construction Contract
                  18    Exhibit 8-- Depository Agreement
                  19    Exhibit 9--- Intercreditor Agreement
</TABLE>

                                       ii


<PAGE>   4



                                                                    Contract No.
                                                                       MA-13304

                      COMMITMENT TO GUARANTEE OBLIGATIONS
                                       by
                          THE UNITED STATES OF AMERICA
                                  accepted by
                              TRAILER BRIDGE, INC.
                                   Shipowner

                               TABLE OF CONTENTS*

                                                                
<TABLE>
<CAPTION>
                                                                                                                             Page
<S>                                                                                                                           <C>
Parties........................................................................................................................1

Recitals.......................................................................................................................1

ARTICLE I                  Findings and Determinations of Secretary............................................................3

ARTICLE II                 Commitment to Guarantee Obligations.................................................................4

ARTICLE III                The Obligations.....................................................................................4

ARTICLE IV                 Covenants of the Shipowner..........................................................................5

ARTICLE V                  Conditions to Execution and Delivery of the
                           Authorization Agreement and the Security
                           Agreement; Conditions to be Fulfilled on
                           the Bond Closing Date...............................................................................6

ARTICLE VI                 Variation of Guarantee Commitment...................................................................9

ARTICLE VII                         Termination or Assignment of Guarantee
                             Commitment........................................................................................9

ARTICLE VIII               Conformity To Regulations..........................................................................10

ARTICLE IX                 Miscellaneous......................................................................................10

                           Signatures.........................................................................................12
</TABLE>

- ----------------
         *This Table of Contents is not a part of the Guarantee Commitment and
has no bearing upon the interpretation of any of its terms and provisions.

                                      iii


<PAGE>   5



Table A

Schedule One to Guarantee Commitment
Appendix I - Form of Bond Purchase Agreement
Appendix II - Form of Trust Indenture
Appendix III - Security Agreement

                                       iv


<PAGE>   6




                      COMMITMENT TO GUARANTEE OBLIGATIONS

                                       by

                          THE UNITED STATES OF AMERICA

                                  Accepted by

                              TRAILER BRIDGE, INC.
                                   Shipowner

                              -------------------

         THIS COMMITMENT TO GUARANTEE OBLIGATIONS, dated as of June 23, 1997
(the "Guarantee Commitment"), made and entered into by the UNITED STATES OF
AMERICA (the "United States"), represented by the SECRETARY OF TRANSPORTATION,
acting by and through the MARITIME ADMINISTRATOR (the "Secretary"), and
accepted on said date by TRAILER BRIDGE, INC. a Delaware corporation (the
"Shipowner").

RECITALS:

     A.   The  Shipowner is proposed to become the sole owner of the two 408'9"
x 100' container deck barges (the "Vessels" when used collectively and each a
"Vessel" when used singularly) to be built pursuant to a certain construction
contract, dated December 30, 1996 (as heretofore or hereafter amended,
including by Amendment No. 1 hereinafter referred to, the "Construction
Contract") originally made with Halter Marine, Inc., a Nevada corporation (the
"Shipyard") by Shipowner's affiliate Coastal Ship, Inc. and assigned to
Shipowner pursuant to Amendment No. 1 thereto dated as of the Closing Date and
by a certain Intercreditor Agreement dated as of the Closing Date among
Shipowner, the Shipyard, and the Secretary, among others.

     B.   To aid in financing the construction of the Vessels, the Shipowner
will borrow an aggregate principal amount approximately equal to, but in no
event in excess of 87 1/2% of the Actual Cost computed as of the Closing Date.

     C.   As one means of such financing, the Shipowner has entered into a bond
purchase agreement (the "Bond Purchase Agreement") with the purchaser named
therein providing for the sale and delivery, on the Closing Date, of not in
excess of $10,515,000 aggregate principal amount of bonds designated "United
States Government Guaranteed Ship Financing Bonds, 1997 Series" (the 
"Obligations") having the maturity date and interest rate set forth in the Bond
Purchase Agreement and the Obligations.

     D.   The Shipowner will on the Closing Date, execute and deliver an
Indenture (the "Indenture"), between the Shipowner and State Street Bank and
Trust Company, as Indenture

                                      -1-


<PAGE>   7



Trustee (the "Indenture Trustee"), in connection with the Obligations to be
issued in respect of the Vessels, in the aggregate amount, with the maturity
and bearing interest at the rate specified in the Trust Indenture.

     E.   Under the Authorization  Agreement (the "Authorization Agreement"),
Contract MA-13305 to be entered into on the Closing Date between the Secretary
and the Indenture Trustee, the Indenture Trustee will be authorized to endorse
and execute, by means of facsimile signature of the Secretary and the facsimile
seal of the Department of Transportation, on each of the Obligations issued and
to authenticate a guarantee by the Secretary of the payment in full of all the
unpaid interest on, and the unpaid balance of the principal of, each
Obligation, including interest accruing between the date of default under such
Obligation and the date of payment by the Secretary (individually, a
"Guarantee" and, collectively, the "Guarantees").

     F.   The Shipowner, as security for the Guarantees, and as security to the
Secretary for the payment to the Secretary of the principal of, and the
interest due or to become due on, the Secretary's  Note to be executed in
accordance with the terms thereof, will, on the Closing Date, enter into a
Security Agreement with the Secretary (the "Security  Agreement"), Contract
MA-13306, pursuant to which the Shipowner will assign to the Secretary, among
other things, all of the Shipowner's interest in the Construction Contract, and
all other contracts which relate to the construction of the Vessels, as
specified therein, and all property, including the Vessels, in which the
Shipowner has or will have an interest pursuant to the Construction Contract.

     G.   The Shipowner will as further security to the Secretary,  execute and
deliver on the date of the delivery of the first Vessel to be delivered
pursuant to the Construction Contract, a First Preferred Fleet Mortgage,
Contract MA-13307, created under and pursuant to Chapter 313, Title 46 United
States Code, to the Secretary, as Mortgagee, upon and attaching to such Vessel
in the form of Exhibit 3 to the Security Agreement (or in the case of the
second Vessel to be delivered, in the form provided for in Exhibit B to said
Exhibit 3).

     H.   In connection with the execution and delivery of the Security
Agreement, the Shipyard will enter into a consent to the assignment of the
Construction Contract (the "Consent of Shipyard").

     I.   In  order to implement certain aspects of the transactions
contemplated by the Security Agreement and the Indenture, the Secretary, the
Shipowner and State Street Bank and Trust Company (the "Depository") will enter
into the Depository Agreement, Contract MA-13308 (the "Depository  Agreement")
and the parties thereto will enter into the Intercreditor Agreement.

     J.   The Shipowner will as further security to the Secretary, enter into a
Title XI Reserve Fund and Financial Agreement, Contract MA-13309, with the
Secretary (the "Title XI Reserve Fund and Financial Agreement").

                              W I T N E S S E T H:
                              --------------------

                                      -2-


<PAGE>   8



         That under the provisions of Title XI of the Merchant Marine Act,
1936, as amended and in effect on the date hereof (said provisions, as so
amended and in effect on the date hereof, being called "Title XI") and in
consideration of (i) the covenants of the Shipowner contained herein, (ii) the
payment by the Shipowner to the Secretary of the charges for this Guarantee
Commitment pursuant to Section 1104(f) of Title XI and (iii) other good and
valuable consideration, the receipt and sufficiency of which are hereby
acknowledged, the Secretary hereby commits itself as herein provided.

         The forms of following executed documents are annexed to each
counterpart of this Guarantee Commitment: the Security Agreement, the Title XI
Reserve Fund and Financial Agreement, and the Depository Agreement.

         Annexed to each counterpart of this Guarantee Commitment are also the
forms of the Construction Contract, Consent of Shipyard, the Bond Purchase
Agreement, the Indenture, the Bonds, the Authorization Agreement, the Mortgage,
the Intercreditor Agreement, and the Secretary's Note. As used herein, the
"Closing Date" refers to the date for the execution and delivery of the
Obligations as provided in the Bond Purchase Agreement annexed hereto, subject
to the conditions contained in Article V hereof.

         The Consent of Shipyard, the Construction Contract, the Security
Agreement, the Title XI Reserve Fund and Financial Agreement, the Intercreditor
Agreement, the Bond Purchase Agreement, the Indenture, the Bonds, the
Authorization Agreement, the Mortgage, and the Secretary's Note (except as
otherwise required by the Secretary), shall be executed and delivered
substantially in the respective forms annexed hereto, except that the blanks,
if any, therein shall be filled in as contemplated therein and herein and,
except further that the interest rates of the Bonds must be further approved by
the Secretary.

                                   ARTICLE I

                    Findings and Determinations of Secretary

         Pursuant to Section 1104(d) of Title XI, the Secretary has found that
the property or project with respect to which the Obligations will be executed
will be, in his opinion, economically sound.

         Pursuant to Sections 1101(f), 1101(g) and 1104(b)(2) of Title XI, the
Secretary has determined that the aggregate of the Actual Cost of the Vessels
is $12,018,052. The Actual Cost for each Vessel is comprised of the amounts
determined by the Secretary set forth in Table A annexed hereto, and the
Secretary has determined that the amounts set forth in said Table A are
itemized as also set forth therein. The Secretary may make a redetermination of
the Actual Cost of one or more of the Vessels to include, in addition to the
items set forth or referred to in said

                                      -3-


<PAGE>   9



Table A, any other items or any increase or decrease in the amounts of the
items set forth or referred to therein.

         On the Closing Date, the aggregate principal amount of the Bonds will
not exceed 87 1/2% of the Actual Cost as of the Closing.

  Pursuant to Section 1104(b)(3) and 1104(b)(5) of Title XI, respectively, 
the Secretary has determined that the maturity date of the Obligations is
satisfactory and that the interest rate to be borne by the Bonds (exclusive of
the charges for the Guarantee Fee and service charges, if any) to be issued on
the Closing Date is reasonable, taking into account the range of interest rates
prevailing in the private market for similar loans and risks assumed by the
Secretary.

         Pursuant to Section 1104(b)(4) of Title XI, the Secretary has
determined that payments of principal required by the Obligations are
satisfactory.

                                   ARTICLE II

                      Commitment to Guarantee Obligations

         The United States, represented by the Secretary, HEREBY COMMITS ITSELF
TO GUARANTEE (as provided in the Obligations) the payment of the unpaid
interest on, and the unpaid balance of the principal of, the Obligations,
including interest accruing between the date of default under the Obligations
and the payment in full of the Guarantees, and, to effect this Guarantee
Commitment, hereby commits itself to execute and deliver the Authorization
Agreement, the Security Agreement, the Title XI Reserve Fund and Financial
Agreement, and the Depository Agreement on the Closing Date and to execute the
Mortgage on each Vessel on the date of her respective delivery.

                                  ARTICLE III

                                The Obligations

     The Obligations shall be as provided in the Indenture and in the form of
the Obligations annexed as Exhibit 2 to the Indenture. The Obligations shall be
subject to all of the terms and conditions set forth in the Indenture and in
the forms thereof. The Indenture, the Bonds, the Secretary's Note, the
Mortgage, the Title XI Reserve Fund and Financial Agreement, and the Depository
Agreement shall be executed and delivered by the Shipowner on (except for the
Mortgage, which the Shipowner covenants to execute upon each Vessel on the
respective date of her delivery) the Closing Date. The forms of the Bond
Purchase Agreement, the Offering Circular, the Indenture, the Obligations, the
Authorization Agreement, the Security Agreement, the Mortgage, the Secretary's
Note, the Title XI Reserve Fund and Financial Agreement, and the Depository
Agreement are hereby approved by the Secretary.

                                      -4-


<PAGE>   10



                                   ARTICLE IV

                           Covenants of the Shipowner

     The Shipowner represents and, until termination of this Guarantee
Commitment, agrees:

                  (a) that each Vessel has been or will be constructed
substantially in accordance with the plans and specifications, as applicable,
pursuant to the Construction Contract in a shipyard within the United States
approved by the Secretary and on the respective delivery date of each Vessel,
each Vessel will be documented under the laws of the United States;

                  (b) to furnish to the Secretary, promptly upon written
request, such reasonable, material and pertinent reports, evidence, proof or
information, in addition to that furnished pursuant to the further provisions
of this Guarantee Commitment or in the application for this Guarantee
Commitment under Title XI or otherwise available to the Secretary, as the
Secretary may reasonably deem necessary or appropriate in connection with the
performance by the Secretary of his duties and functions under the Act;

                  (c)  to maintain records of all amounts paid or obligated
to be paid by or for the account of the Shipowner for the construction of each
Vessel;

                  (d)  to permit the Secretary, promptly upon request, to
make such reasonable, material and pertinent examination and audit of the
Shipowner's books, records and accounts and to take such information therefrom
and make such transcripts or copies thereof, as the Secretary may reasonably
deem necessary or appropriate in connection with the performance by the
Secretary of his duties and functions under the Act;

                  (e) to maintain its United States citizenship within the
meaning of Section 2 of the Shipping Act, 1916, as amended, for the purpose of
operation of the Vessels in the trade or trades in which the Shipowner proposes
to operate the Vessels, to the satisfaction of the Secretary and, at the time
of the execution and delivery of the Authorization Agreement, to submit to the
Secretary such supplemental proof of citizenship as the Secretary may deem
appropriate to evidence the continued United States citizenship of the
Shipowner for said purpose; and

                  (f) to execute and deliver the Bond Purchase Agreement, the
Bonds, the Security Agreement, the Indenture, the Secretary's Note, the
Mortgage, the Title XI Reserve Fund and Financial Agreement, the Consent of
Shipyard and the Depository Agreement.

                                      -5-

<PAGE>   11



                                   ARTICLE V

                  Conditions to Execution and Delivery of the
               Authorization Agreement and the Security Agreement

         On the Closing Date, the Authorization Agreement shall be executed and
delivered by the United States and the Indenture Trustee; the Security
Agreement and the Title XI Reserve Fund and Financial Agreement shall be
executed and delivered by the Shipowner and the Secretary; the Indenture shall
be executed and delivered by the Shipowner and the Indenture Trustee; the
Construction Contract shall have been executed and delivered by the Shipowner
and the Shipyard; the Consent of the Shipyard shall be executed and delivered
by the Shipyard; the Intercreditor Agreement shall have been executed and
delivered by all parties thereto; the Depository Agreement shall be executed
and delivered by the Shipowner, the Secretary and the Depository; the
Secretary's Note shall be executed and delivered and the Bonds shall be issued
and delivered by the Shipowner; and the Bond Purchase Agreement shall be
executed and delivered by the Shipowner and the purchaser of the Bonds. The
obligation of the United States represented by the Secretary to execute and
deliver the Authorization Agreement, the Security Agreement, the Mortgage, the
Depository Agreement and the Title XI Reserve Fund and Financial Agreement on
the Closing Date shall be subject to the following conditions unless waived in
writing by the Secretary:

          (a) the Closing Date shall occur prior to September 26, 1997;
          
          (b) on the Delivery Date, each Vessel shall be free of any claim,
lien, charge, mortgage or other encumbrance of any character (except the
Security Agreement, and liens otherwise permitted by Section 2.04 of Exhibit 1
to the Security Agreement); and on the Closing Date the Bond Purchase Agreement
shall have been executed and delivered on or prior to the Closing Date and the
Indenture and the Obligations shall have been duly executed and delivered on
the Closing Date;

          (c)  on the Closing Date, the Shipowner shall be a citizen of the
United States within the meaning of Section 2 of the Shipping Act, 1916, as
amended, and shall have furnished to the Secretary an affidavit setting forth
data showing such citizenship to the Secretary's satisfaction at least 20 days
prior to the Closing Date and the Shipowner shall have submitted pro forma
affidavits at least ten days prior to the Closing Date;

          (d)  (i) there shall have been delivered to the Secretary two
executed counterparts of the Bond Purchase Agreement, and two executed
counterparts of the Indenture, (ii) two specimen copies of the Obligations
issued under the Indenture; and (iii) two copies of all other documents
delivered by the Shipowner or the Indenture Trustee on the Closing Date;

          (e)  the following representations and warranties shall have been
made to the Secretary in writing and shall be true as of the Closing Date:

                                      -6-


<PAGE>   12



          (i)  the Shipowner is a corporation duly organized, validly existing
     and in good standing under the laws of the State of Delaware, has not
     failed to qualify to do business in any jurisdiction in the United States
     in which its business or properties require such qualification, and had
     and has full legal right, corporate power and authority to own its own
     properties and assets and conduct its business as it is presently
     conducted;

          (ii) the Shipowner had and has legal power and authority to enter
     into and carry out the terms of this Guarantee Commitment, the
     Construction Contract, the Bond Purchase Agreement, the Obligations, the
     Indenture, the Security Agreement, the Secretary's Note, the Mortgage, the
     Title XI Reserve Fund and Financial Agreement, the Intercreditor
     Agreement, and the Depository Agreement;

          (iii) each and all of the documents and instruments referred to in
     clause (ii) hereof have been duly authorized, executed and delivered by
     the Shipowner and constitute, in accordance with their respective terms,
     legal, valid and binding instruments enforceable against the Shipowner,
     except to the extent limited by applicable bankruptcy, reorganization,
     insolvency, moratorium or the similar laws of general application relating
     to or affecting the enforcement of creditors rights as from time to time
     in effect;

          (iv) the consummation of the transactions contemplated by and
     compliance by the Shipowner of all the terms and provisions of the
     documents and instruments referred to in clause (ii) hereof will not
     violate any provisions of the Certificate of Incorporation or By-laws of
     the Shipowner and will not result in a breach of the terms and provisions
     of, or constitute a default under any other agreement or undertaking by
     the Shipowner or by which the Shipowner is bound or any order of any court
     or administrative agency entered into in any proceedings to which the
     Shipowner is or has been a party;

          (v)  there is no litigation, proceeding or investigation pending or,
     to the best of the Shipowner's knowledge, threatened, involving the
     Shipowner or any of its property which could prevent or jeopardize the
     performance by the Shipowner of the documents and instruments referred to
     in clause (ii) hereof.

     (f)  there shall have been delivered to the Secretary a copy of each
document and legal opinion delivered to the Purchasers of the Obligations on
the Closing Date;

     (g) the Secretary shall have received the initial Guarantee Fee payable
under the Security Agreement;

     (h)  all charges levied or assessed by the Secretary under Section 1104(f)
of Title XI shall have been paid by the Shipowner;

     (i)  the Shipowner shall have performed without material breach its
agreements under Article IV hereof, and the further terms, conditions and
provisions of this Guarantee Commitment shall have been complied with in all
material respects;

                                      -7-


<PAGE>   13




     (j)  there shall not have occurred any event which constitutes (or after
any period of time or any notice, or both, would constitute) a "Default" under
the Security Agreement;

     (k)  there shall have been delivered to the Secretary by the Shipowner an
opinion (or opinions) of counsel acceptable to the Secretary, and in form and
substance satisfactory to the Secretary, to the effect that:

     (i)  by the terms of the Security Agreement, the Shipowner has granted to
the Secretary a fully perfected, first priority security interest in each of
the assets which constitutes the Security, as defined therein;

          (ii) all filings and recordings required or available to perfect the
    Secretary's first priority security interests in the Security, as
    defined in the Security Agreement, granted by the Shipowner in the Security
    Agreement, and to render such security interests valid and enforceable
    under the laws of the States of Mississippi and Florida (including without
    limitation, all filings of financing statements under the UCC) have been
    duly effected, and no periodic refiling or periodic re-recording is
    required to protect and preserve the perfection and first priority of such
    security interests, except as provided by the laws of such State;

          (iii) all agreements have been executed and all action has been taken
    which are required under the laws of the Commonwealth of Massachusetts
    to establish a bailment by the Shipowner/Secretary/Bailor of the amounts
    held or to be held by the Depository/Bailee under the Depository Agreement,
    at whatever time, whether such amounts are cash, instruments, negotiable
    documents, chattel paper, proceeds thereof or otherwise (the "Funds"), in
    order to insure that the Secretary has a fully perfected first priority
    security interest in the Funds;

     (l)  there shall have been executed and delivered to the Secretary an
opinion of counsel to the effect stated in the form annexed hereto as Schedule
One;

     (m)  the Secretary shall have received a letter agreement from the
Shipowner to provide the Secretary within a reasonable time after the Closing
Date, with seven conformed copies of the Guarantee Commitment and each of the
Appendices and Exhibits thereto executed on or prior to such date;

     (n)  on the Closing Date, the qualifying requirements set forth in Section
15 of the Title XI Reserve Fund and Financial Agreement shall have been
complied with and certified to as required therein;

     (o)  at least ten days prior to the Closing Date, there shall have been
delivered to the Secretary, pro forma balance sheets for the Shipowner as of
the Closing Date, certified by an officer of the Shipowner showing, among other
things, all non-Title XI debt of the Shipowner;

                                      -8-


<PAGE>   14



     (p)  on the Closing Date, the Shipowner shall certify that all non-Title
XI loans to the Shipowner relating to the Vessels have been discharged save
only such as Shipowner expects to pay from the proceeds of the Obligations; and

     (q)  at least ten days prior to the Closing Date the Secretary shall have
been furnished evidence that the Vessels have been insured as required by the
Secretary,

                                   ARTICLE VI

                       Variation of Guarantee Commitment

     No variation from the terms and conditions hereof shall be permitted
except pursuant to an amendment executed by the Secretary and accepted by the
Shipowner.

                                  ARTICLE VII

               Termination or Assignment of Guarantee Commitment

     This Guarantee Commitment may terminate and the parties hereto shall have
no further rights or obligations hereunder, upon written notice by the
Secretary, after the earlier of (a) the termination of the obligations of the
United States pursuant to the Shipowner's failure to satisfy one or more
conditions set forth in Article V hereof or (b) the execution and delivery of
the Security Agreement and the Authorization Agreement.

     This Guarantee Commitment may not be assigned by the Shipowner without the
prior written approval of the Secretary and any attempt to do so shall be null
and void ab initio.

                                  ARTICLE VIII

                          Conformity with Regulations

     The Secretary hereby affirms that, with respect to the rights of the
Indenture Trustee and the Holders of the Obligations, this Guarantee Commitment
conforms to its existing regulations governing the issuance of commitments to
guarantee and guarantees under Title XI of the Act and that this Guarantee
Commitment contains a complete list of conditions required for the execution
and delivery of guarantees including the Guarantees.

                                   ARTICLE IX

                                 Miscellaneous


     (a)  The table of contents

                                      -9-
<PAGE>   15

and the titles of the Articles are inserted as a matter of convenient
reference and shall not be construed as a part of this Guarantee Commitment.
This

                                      -10-


<PAGE>   16



Guarantee Commitment may be executed in any number of counterparts, each of
which shall be an original, but such counterparts shall together constitute but
one and the same instrument.

         (b) For all purposes of this Guarantee Commitment, unless otherwise
expressly provided or unless the context shall otherwise require:

                  (i) The terms "hereof," "herein," "hereby," "hereto,"
"hereunder," "hereinafter" and "herewith" refer to this Guarantee Commitment as
the same may be supplemented or amended as herein provided.

                  (ii) Terms defined in Schedule X of the Security Agreement
annexed hereto or by reference therein to other instruments shall have the
respective meanings stated in Schedule X or such other instruments.

     IN WITNESS WHEREOF, this Commitment to Guarantee Obligations has been
executed by the United States and accepted by the Shipowner, all as of the day
and year first above written.

                                                 UNITED STATES OF AMERICA,
                                                SECRETARY OF TRANSPORTATION

                           BY: MARITIME ADMINISTRATOR

(SEAL)

                              BY: Joel C. Richard

                                   Secretary

                                                         Maritime Administration

Attest:

Larry Main

Assstant Secretary
Maritime Administration

                                                     ACCEPTED BY:

                              TRAILER BRIDGE, INC.

                                                              as Shipowner

                                                     BY: John McCown

(SEAL)

Attest:
BY: William G. Gotimer, Jr.

                                      -11-


<PAGE>   17



                                   TABLE A

     The aggregate Actual Cost of the Vessels Hull No. 287 and Hull No. 288 as
of the date hereof as determined by the Secretary (namely, (i) the amounts paid
by or for the account of the Shipowner as of the date hereof for the
Construction of the Hull No. 287 and Hull No. 288, plus (ii) the amount which
the Shipowner was on said date obligated under the Construction Contract or
otherwise to pay from time to time thereafter for the Construction of the Hull
No. 287 and Hull No. 288) is $12,018,052 calculated and itemized as follows :

<TABLE>
<CAPTION>
                                                                       Amount*
                                                     Amount*           Obligated
                                                      Paid             To be Paid             Total
<S>                     <C>           <C>              <C>               <C>                    <C>
Contract Price                        Hull 287         5,768,806
                        Hull 288                                                                5,768,806
Design, Engineering
and Inspection                                          96,000

Net Interest During

Construction                                                                                                  144,220
Total Actual Cost

 Per Vessel                                                                                                   6,009,026

Number of Vessels
         2

Total Actual Cost                                                                                         12,018,052

</TABLE>

*        The Secretary has not yet made findings as to the amounts actually
         paid to date by the Shipowner (or hence as to the remaining amounts
         which the Shipowner is obligated to pay in the future).

                                     -11-


<PAGE>   18




              SCHEDULE ONE TO COMMITMENT TO GUARANTEE OBLIGATIONS:
                         FORM OF OPINION(S) OF COUNSEL

                                      -12-


<PAGE>   19







                                     -12-


<PAGE>   20







                                     -13-


<PAGE>   21






                                     -14-



<PAGE>   1


                                                                 EXHIBIT 10.8.1
                                                                         10.8.1

                                                                 APPENDIX III --
                                                         Form of Trust Indenture
<PAGE>   2





            _____________________________________________________


                                TRUST INDENTURE


                Relating to United States Government Guaranteed
                           Ship Financing Obligations



                                    Between



                              TRAILER BRIDGE, INC.

                                   Shipowner



                                      AND



                      STATE STREET BANK AND TRUST COMPANY

                               Indenture Trustee




                           Dated as of June 23, 1997





          _________________________________________________________
<PAGE>   3


                                TRUST INDENTURE

                Relating to United States Government Guaranteed
                           Ship Financing Obligations

                                    Between

                              TRAILER BRIDGE, INC.

                                   Shipowner

                                      AND

                      STATE STREET BANK AND TRUST COMPANY

                               Indenture Trustee

                           Dated as of June 23, 1997

          TABLE OF CONTENTS TO SPECIAL PROVISIONS OF THE INDENTURE  (1)


<TABLE>
<CAPTION>
                                                                                                                     Page 
                                                                                                                     ---- 
<S>                                                                                                                    <C>
Parties . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1
Recitals  . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1

                                                           ARTICLE FIRST

Incorporation of General Provisions . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2

                                                          ARTICLE SECOND

The Bonds . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2

                                                           ARTICLE THIRD

Certain Redemptions . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 3

(a) Mandatory Sinking Fund Redemptions  . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 3
(b) [Reserved . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 3
(c) Optional Redemptions of Bonds at Premium  . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 4
         ------------------                                                                                              
(1) This Table of Contents is not a part of the Indenture and has no bearing upon the interpretation of any of its terms
and provisions.
</TABLE>
                                   i         
<PAGE>   4


                                 ARTICLE FOURTH

<TABLE>
<S>                                                                                                             <C>
Definitions . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 4
                                                 ARTICLE FIFTH

Additions, Deletions and Amendments to Exhibit 1  . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 5
 1
(a) Concerning Section 2.04 . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 5
(b) Concerning Section 2.12 . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 5
(c) Concerning Payment of the Obligations . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 5
(d) Concerning Selection of Bonds to be Redeemed  . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 6
(e) Concerning References to 3.09(b)  . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 6
(f) Concerning Home Office Payment  . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 6
(g) Concerning Section 7.02 . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 6
(h) Concerning Section 10.01  . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 7
(i) Concerning Notices  . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 7
(j) Concerning Applicable Law . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 7
(k) Execution in Counterparts . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 8

Signatures  . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 9

Acknowledgements  . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 10 and 11


                                          EXHIBITS TO TRUST INDENTURE
                                          ---------------------------


SCHEDULE A       Schedule of Definitions to Trust Indenture

EXHIBIT 1        General Provisions of the Indenture
                 Incorporated by Reference

EXHIBIT 2        Forms of Bond, Guarantee and Trustee's
                 Authentication Certificate

EXHIBIT 3        Authorization Agreement

EXHIBIT 4        Form of Secretary Supplemental Indenture

</TABLE>



                                       ii
<PAGE>   5


                                TRUST INDENTURE

                               SPECIAL PROVISIONS


         THIS TRUST INDENTURE, dated as of June 23, 1997 (said Trust Indenture,
as the same may be amended, modified or supplemented from time to time as
permitted hereunder, herein called the "Indenture"), between (i)Trailer Bridge,
Inc., a Delaware corporation (herein called the "Shipowner"), and (ii) State
Street Bank and Trust Company, a Massachusetts trust company (said Bank, any
successor or assign hereunder, herein called the "Indenture Trustee").

                                        RECITALS:

         A. As provided in Article Fourth hereof, the terms defined in Schedule
A to this Indenture shall have the respective meanings stated in said Schedule;

         B. The Shipowner has duly executed this Indenture, and duly authorized
the issuance hereunder of $10,515,000 aggregate principal amount of its bonds
pursuant to Section 2.03 of Exhibit 1 to this Indenture (herein together with
any bonds issued in respect thereof pursuant to Sections 2.09, 2.10, 2.12 and
3.10(b) of said Exhibit 1, called the "Bonds" or the "Obligations") designated
"United States Government Guaranteed Ship Financing Bonds, 1997 Series;" the
Obligations will bear interest at 7.07% per annum and mature on September 30,
2022;

         C. The Obligations will be issued by the Shipowner to aid in the
financing of the cost of construction of two 408'9" x 100' container deck
barges;

         D. Under the Authorization Agreement in the form set forth as Exhibit
3 hereto, the Secretary, on behalf of the United States, has agreed and will
agree to execute on each of the Obligations to be issued, a Guarantee of the
payment of the unpaid interest to the date of such payment on, and the unpaid
balance of the principal of, such Obligation under the provisions of Title XI
of the Act, and the Indenture Trustee is authorized to cause the Guarantees,
bearing the facsimile signature of the Secretary, and the facsimile seal of the
United States Department of Transportation, to be imprinted on the Obligations,
and to authenticate and deliver the Obligations and the Guarantees issued on
the Closing Date, such agreements and authorizations being subject to the
conditions set forth in the Authorization Agreement;

         E. Pursuant to Section 1104(b)(5) of the Act, the Secretary has
determined that the interest to be borne by the Obligations (exclusive of
charges for the guarantee fee and service charges, if any) at the rate
specified in the form thereof set forth in Exhibit 2 hereto is reasonable; and

         F. All actions necessary have been taken in order (1) to make the
Obligations, when





                                       1
<PAGE>   6

executed by the Shipowner, authenticated by the Indenture Trustee and issued
under the Indenture, the valid, binding and legal obligations of the Shipowner
in accordance with their terms, (2) to make the Guarantees to be endorsed on
the Obligations, when executed by the Secretary, authenticated by the Indenture
Trustee and delivered under this Indenture, the valid, binding and legal
obligations of the United States in accordance with their terms, and (3) to
make this Indenture the valid, binding and legal agreement of the parties
hereto in accordance with its terms.

         NOW THEREFORE, in consideration of the premises, of the mutual
covenants herein contained, of the purchase of the Obligations by the Holders
thereof, and of other good and valuable consideration, the receipt and adequacy
of which the parties hereby acknowledge, and for the equal and proportionate
benefit of all the present and future Holders of the Obligations, the parties
hereto agree as follows:

                                 ARTICLE FIRST

                      INCORPORATION OF GENERAL PROVISIONS

         This Indenture shall consist of two parts: the Special Provisions and
the General Provisions attached hereto as Exhibit 1, made a part of this
Indenture and incorporated herein by reference.

                                 ARTICLE SECOND

                                   THE BONDS

         (a) The Bonds issued hereunder shall be designated "United States
Government Guaranteed Ship Financing Bonds, 1997 Series," and shall be in the
form of Exhibit 2 to this Indenture; and, the aggregate principal amount of
Bonds which may be issued under this Indenture shall not exceed $10,515,000
except as provided in Sections 2.09, 2.10, 2.12 and 3.10(b) of Exhibit 1
hereto.

         (b) The Bonds shall be in the denominations of $1,000 or any integral
multiple thereof.

         (c) The Shipowner shall at the date of the Closing maintain in
Jacksonville, Florida an office or agency for the purposes specified in Section
5.03 of Exhibit 1 to this Indenture.

         (d) The Indenture Trustee shall at the date of the Closing have its
Corporate Trust Office in the City of Boston, Commonwealth of Massachusetts.





                                       2
<PAGE>   7


         (e) The Bonds shall mature on September 30, 2022.

                                 ARTICLE THIRD

                              CERTAIN REDEMPTIONS

         (a) Mandatory Sinking Fund Redemptions. The Bonds are subject to
redemption at a Redemption Price equal to 100% of the principal amount thereof,
together with interest accrued thereon to the applicable sinking fund
Redemption Date, through the operation of a mandatory sinking fund providing
for the semi-annual redemption on March 30 and September 30 of each year,
commencing March 30, 1998, of $210,300 principal amount of Bonds (or such
lesser principal amount of Bonds as shall then be outstanding), which amount
represents two percent (2%) of the Original Principal Amount of Obligations,
plus interest accrued thereon to the Redemption Date. On September 30, 2022
there shall become due and payable, and the Shipowner shall pay, the balance of
the unpaid principal amount of Bonds then outstanding, together with all
interest accrued thereon to such date.

         Notwithstanding the foregoing provisions of this subsection (a), if
the principal amount of Outstanding Bonds shall be reduced by reason of any
redemption pursuant to Sections 3.04 or 3.05 of Exhibit 1 to this Indenture,
the principal amount of Bonds to be redeemed pursuant to this subsection (a) on
each subsequent mandatory sinking fund Redemption Date for such Bonds shall be
reduced by an amount equal to the principal amount of such Bonds retired by
reason of such redemption pursuant to Sections 3.04 or 3.05 of Exhibit 1 hereto
divided by the number of mandatory sinking fund Redemption Dates (including the
Stated Maturity of such Bonds) scheduled thereafter (subject to such increase
as shall be necessary so that the total principal amount of Bonds to be
redeemed on any such sinking fund redemption date shall be an integral multiple
of $1,000; provided that, the entire unpaid principal amount of the Outstanding
Bonds shall be paid not later than September 30, 2022. The Shipowner shall, in
accordance with Section 3.02(d) of Exhibit 1 hereto, promptly after each
redemption pursuant to said Section 3.04, furnish to the Secretary, the
Indenture Trustee and each Holder of an Obligation a revised table of sinking
fund payments reflecting the reductions made pursuant to this subsection (a) as
a result of such redemption.

         In lieu of making all or any part of any such mandatory sinking fund
redemption of Bonds, the Shipowner may, at its option, with the prior written
consent of the Secretary, receive credit for Bonds not previously so credited
or applied to reduce the principal amount of Bonds Outstanding, (i) redeemed by
the Shipowner pursuant to the optional redemption provision provided for in
subsection (c) of this Article or purchased or acquired by the Shipowner (other
than by redemption) and delivered to the Indenture Trustee for cancellation
pursuant to Section 2.13 of Exhibit 1 hereto. The Bonds so credited or applied
shall be credited or applied, as the case





                                       3
<PAGE>   8

may be, by the Indenture Trustee, at 100% of the principal amount thereof. If
the Shipowner shall elect to receive credit or application as aforesaid in lieu
of making all or part of any mandatory sinking fund redemption, it shall
deliver to the Indenture Trustee, at least 40 days but not more than 60 days
prior to the due date for such mandatory sinking fund redemption, a Request (i)
specifying the principal amount of Bonds so optionally redeemed or otherwise
acquired, and so to be credited or applied, as the case may be, and (ii)
stating that no such Bonds have theretofore been made the basis of any such
credit or application as aforesaid, and that none of such Obligations are
subject to the terms of any agreement or contract between the Secretary, the
Shipowner and/or any other person restricting the Shipowner's right to apply
any such Obligations as a credit pursuant to the terms of this subsection (a),
together with the Bonds (uncancelled) for which such credit or application is
so requested (unless such Bonds shall theretofore have been delivered to the
Indenture Trustee).

         (b) [Reserved]


         (c) Optional Redemptions of Bonds at Premium. At its option, the
Shipowner may redeem the Bonds, in whole at any time, at the redemption prices
as specified  in the Bonds, together with interest accrued thereon to the date
fixed for redemption; provided that, no such redemption shall be made prior to
March 30, 2008, directly or indirectly with the proceeds of, or in anticipation
of, borrowing by or for the account of the Shipowner if such borrowing has an
effective interest cost (calculated in accordance with generally accepted
financial practice) of less than the rate of interest borne by the Bonds. If
the Shipowner shall elect to make any such optional redemption, the Shipowner
shall, at least 30 days but not more than 60 days prior to the date fixed for
redemption, deliver to the Indenture Trustee a Request stating that the
Shipowner intends to exercise its rights as above set forth to make such
optional redemption and specifying the Redemption Date, and the principal
amount of Bonds which the Shipowner intends to redeem on such date (which shall
not be less than all the Bonds outstanding). In the case of any redemption
pursuant to this subsection (c) prior to March 30, 2008, the Shipowner shall
deliver to the Indenture Trustee, at the time of delivery of said Request, an
Officer's Certificate stating that such redemption shall comply with the
proviso relating to such redemption prior to such date.

                                 ARTICLE FOURTH
                                  DEFINITIONS

         For all purposes of this Indenture, unless otherwise expressly
provided or unless the context otherwise requires:

        (1) All references herein to Articles, Sections or other subdivisions,
            unless





                                       4
<PAGE>   9

                otherwise specified, refer to the corresponding Articles,
                Sections and other subdivisions of this Indenture;

                          (2) The terms "hereof," "herein," "hereby," "hereto,"
                "hereunder" and "herewith" refer to this Indenture;

                          (3) The terms used herein and defined in Schedule A
                to this Indenture shall have the respective meanings stated in
                said Schedule.

                                ARTICLE FIFTH

               ADDITIONS, DELETIONS AND AMENDMENTS TO EXHIBIT 1

         The following additions, deletions and amendments are hereby made to
Exhibit 1 to this Indenture.


         (a) Concerning Section 2.04. The Shipowner and the Indenture Trustee
shall not enter into any Supplemental Indenture, and the Indenture Trustee
shall not enter into any supplement to the Authorization Agreement, pursuant to
Section 2.04 of Exhibit 1 to this Indenture, except to provide for the issuance
of additional Obligations of any series and Stated Maturity theretofore issued,
or of one or more additional series for the purpose of aiding in financing or
refinancing the construction, reconstruction or reconditioning of one or more
of the Vessels, or to refund Obligations issued for such purpose.

         (b) Concerning Section 2.12. With respect to clause (1) of the proviso
to Section 2.12 of Exhibit 1 to the Indenture, a written agreement of indemnity
which is satisfactory in form and substance to the Secretary, the Shipowner,
and the Indenture Trustee, executed and delivered by an institutional Holder
having a combined capital and surplus of at least one hundred million dollars
($100,000,000) shall be considered sufficient indemnity to the Secretary, the
Shipowner, and the Indenture Trustee in connection with the execution,
authentication and delivery of any new Obligations or the making of any payment
as contemplated by said Section 2.12.

         (c) Concerning Payment of the Obligations. Notwithstanding anything to
the contrary in Exhibit 1 hereto, the Obligations to be issued hereunder shall
be payable as to principal, premium (if any), and interest, at an office or
agency maintained by the Shipowner for such purpose at the Corporate Trust
Office of the Indenture Trustee, or at the option of the Shipowner, as to
payments of principal, premium (if any), or interest by check mailed by such
Corporate Trust Office to the addresses of the Obligees as such addresses shall
appear in the Obligation Register, subject in any event to the provisions
hereof concerning home office payment. The Indenture Trustee agrees that within
30 days from the date of any payment of principal or interest when the





                                       5
<PAGE>   10

same shall become due and payable by reason of maturity or redemption, a
Responsible Officer in the Corporate Trust Office of the Indenture Trustee
shall ascertain to his satisfaction that checks in payment of such amounts have
been mailed by such Corporate Trust Office to the addresses of the Obligees as
provided above, if payment is to be made by check, or if payment is to be made
by wire transfer, or by credit to an account maintained by the Obligee with the
Indenture Trustee, that such funds have been wired or credited, or if payment
is to be made at the Corporate Trust Office, that funds were held by the
Indenture Trustee for such payment on the date the payment was due. The
Indenture Trustee shall have no obligation to determine whether such checks or
payments were received by the Obligees.

         (d) Concerning Selection of Bonds to be Redeemed. Notwithstanding the
provisions of Section 3.07(b) of Exhibit 1 to this Indenture, (i)  if less than
all the Bonds are to be optionally redeemed under any of the provisions
contained or referred to in Article Third hereof or Article III of Exhibit 1,
the Indenture Trustee shall select for redemption Bonds of the Stated Maturity
or Stated Maturities, and (ii) if less than all the Bonds of a particular
Stated Maturity are to be redeemed under any provisions contained or referred
to in Article Third hereof or Article III of Exhibit I to this Indenture, the
Indenture Trustee shall select the particular Bonds and/or portions ($1,000 or
any integral multiple thereof) of Bonds to be redeemed on the Redemption Date
by allocating the principal amount to be redeemed among the Holders of Bonds of
such Stated Maturity in proportion to the respective principal amount of Bonds
of such Stated Maturity registered in their respective names.

         (e) Concerning Section 3.08(a).  Section 3.08 (a) of Exhibit 1 is
amended by adding the following after the word "Register": "provided, however,
that the requirement in this Section 3.08(a) to include the Redemption Price in
such notice may be satisfied by stating (i) the principal amount of Obligations
being redeemed, (ii) that the Shipowner is obligated to pay such amount,
together with accrued interest at the interest rate borne by the Obligations to
the Redemption Date and the Redemption Premium, and (iii) that the Shipowner
shall calculate the Redemption Premium and furnish such calculation, together
with a reasonably detailed summary thereof, to the Indenture Trustee and each
Holder not later than the second Business Day preceding the Redemption Date."

        (f) Concerning References to Section 3.09(b).  All cross-references to
Section 3.09(b) made in Exhibit 1 hereto shall be deemed to refer to Section
3.10(b) of Exhibit 1 hereto.                    

        (g) Concerning Home Office Payment.  Notwithstanding any terms of
this Indenture or the Obligations to the contrary, the Shipowner may enter into
an agreement with any Holder of an Obligation providing for payment to such
Holder by certified or official bank check, or at the request of such Holder, by
credit to an account maintained by the Holder with the Indenture Trustee, or by
wire transfer of the principal of and the premium (if any), and interest on such





                                      6
<PAGE>   11

Obligation or any part thereof at a place other than the place or places
specified in such Obligation as the place for such payment, and for the making
of notation (if any), of such payment on such Obligation by such Holder, or by
an agent of the Shipowner or of the Indenture Trustee without presentation of
such Obligation. The Shipowner will furnish to the Indenture Trustee a copy of
each such agreement. The Indenture Trustee hereby consents to such agreement
contained in Section 7 of the Bond Purchase Agreement dated as of the Closing
Date, between the Shipowner and the Purchasers named in Schedule 1 thereto, and
hereby acknowledges receipt of a copy thereof.

         (h) Concerning Section 7.02. The amount "$3,000,000" in Section 7.02
of Exhibit 1 hereto is hereby deleted, and there is substituted therefor the
amount "$100,000,000."

         (i) Concerning Section 10.01. Paragraph (2) of Section 10.01 of
Exhibit 1 to this Indenture is deleted, and the following substituted in lieu
thereof:

                 "(2) to evidence the succession pursuant to Article VIII of
                 another corporation or entity to the Shipowner or any 
                 assumption of all or a part of the Obligations pursuant to 
                 Article VIII;"

         (j) Concerning Notices.  Subject to the provisions of Section 13.01 of
Exhibit 1 to this Indenture, any notice, request, demand, direction, consent,
waiver, approval or other communication to be given to a party hereto or the
Secretary, shall be deemed to have been sufficiently given or made when
addressed to:

<TABLE>
<S>                               <C>
The Indenture Trustee as:                  State Street Bank and Trust Company
                                           Corporate Trust Department
                                           Two International Place
                                           Boston, Massachusetts 02110

The Shipowner as:                          Trailer Bridge, Inc.
                                           9550 Regency Square Boulevard
                                           Jacksonville, Florida 32225
                                           Attention: John McCown



The Secretary as:                 SECRETARY OF TRANSPORTATION
                                  c/o Maritime Administrator
                                  Department of Transportation
                                  400 Seventh Street, SW

</TABLE>




                                      7
<PAGE>   12

                             Washington, D.C. 20590

         (k) Concerning Applicable Law. This Indenture and each Obligation
shall be governed by the laws of the State of New York, and to the extent
applicable, the federal laws of the United States.

         (l) Execution in Counterparts. This Indenture may be executed in any
number of counterparts. All such counterparts shall be deemed to be originals,
and shall constitute but one and the same instrument.





                                      8
<PAGE>   13

         IN WITNESS WHEREOF, this Trust Indenture has been duly executed by the
parties hereto as of the day and year first above written.

<TABLE>
<S>                                                <C>
                                                   TRAILER BRIDGE, INC.
                                                         Shipowner



[SEAL]                                             By: John McCown
                                                       -----------



                                                   STATE STREET BANK AND TRUST
COMPANY
                                                       Indenture Trustee



                                                   By: Gerald R. Wheeler
                                                       -----------------
                                                          Vice President
[SEAL]

</TABLE>




                                      9
<PAGE>   14



STATE OF NEW YORK     )
                      ) SS:
COUNTY OF NEW YORK    )

         On this 20 day of June, 1997 before me personally appeared John
McCown, who being by me duly sworn, did depose and say that he resides at 40
Radcliffe Drive, Woodstock, New York 12948; that he is Chairman of TRAILER
BRIDGE, INC., that he knows the seal of said Corporation; that the seal affixed
to said instrument is such corporation's seal; that it was so affixed by
authority of the Board of Directors of said corporation, and that he signed his
name thereto by like authority.

         In testimony whereof, I have hereunto set my hand and seal this 20 day
of June, 1997.


<TABLE>
<S>                                                <C>
                                                   William G. Gotimer, Jr.
                                                   -----------------------
                                                   NOTARY PUBLIC
                                                   State of New York
                                                   02604837705
                                                   Comm. Expires 7/31/97



(Notarial Stamp and Seal)

</TABLE>




                                      10
<PAGE>   15



COMMONWEALTH OF MASSACHUSETTS)
                                    ) SS:
COUNTY OF SUFFOLK            )



                 Be it known this 17 day of June, 1997 personally appeared
before me Gerald R. Wheeler, who after being duly sworn, deposed and said that
he is a Vice President of STATE STREET BANK AND TRUST COMPANY, the
Massachusetts Trust Company which is described in and executed within the
instrument hereto annexed, that he/she knows the seal of said trust company,
that the seal affixed to said instrument is said trust company's seal, that it
was so affixed and that he/she signed the instrument hereto annexed by order of
the Board of Directors of the said STATE STREET BANK AND TRUST COMPANY, and
that he/she signed his/her name thereto by like authority, and acknowledged the
annexed instrument to be the free act and deed of the said STATE STREET BANK
AND TRUST COMPANY.

         In testimony whereof, I have hereunto set my hand and seal this 17 day
of June, 1997.


<TABLE>
<S>                               <C>                                       
                                  Virginia F. Brady                         
                                  -----------------                         
                                  NOTARY PUBLIC                             


                                             Virginia F. Brady
                                               Notary Public
                                            My Commission Expires June 20, 1997
(Notarial Stamp and Seal)
</TABLE>





                                      11
<PAGE>   16
                                                                     Document 5

                                                 EXHIBIT 1 to Trust Indenture--
                                                             General Provisions
                                                              Incorporated into
                                                            the Trust Indenture
                                                                   by Reference

<PAGE>   17

                                   EXHIBIT 1
                      GENERAL PROVISIONS OF THE INDENTURE
                           INCORPORATED BY REFERENCE
                               TABLE OF CONTENTS
                                       TO
                                   EXHIBIT 1*

<TABLE>
<CAPTION>
                                                                                                                Page
<S>                                                                                                              <C>
ARTICLE I.    DEFINITIONS; OFFICER'S CERTIFICATE AND OPINIONS OF COUNSEL..........................................1
SECTION 1.01.  Definitions........................................................................................1
SECTION 1.02.  Officer's Certificate and Opinions of Counsel......................................................1

ARTICLE II.   THE OBLIGATIONS.....................................................................................2
SECTION 2.01.  Designation of Obligations.........................................................................2
SECTION 2.02.  Issue, Form, Principal Amount, Maturity,
                   Interest, Place of Payment, Denominations,
                   and Redemption of Obligations..................................................................2
SECTION 2.03.  Issuance of Obligations of
                   Initial Series.................................................................................3
SECTION 2.04.  Additional Obligations;
                   Obligations of Additional Series...............................................................3
SECTION 2.05.  Legends on Obligations.............................................................................4
SECTION 2.06.  Dates of Obligations; Interest Rights..............................................................4
SECTION 2.07.  Execution of Obligations...........................................................................4
SECTION 2.08.  Authentication of Obligations and
                   Guarantees.....................................................................................4
SECTION 2.09.  Temporary Obligations..............................................................................5
SECTION 2.10.  Registration, Transfer and Exchange................................................................5
SECTION 2.11.  Who Treated as Owners..............................................................................6
SECTION 2.12.  Lost, Stolen, Destroyed or
                   Mutilated Obligations..........................................................................6
SECTION 2.13.  Reacquired Obligations, Cancellation
                   and Disposition of Obligations.................................................................7

ARTICLE III.  REDEMPTION OF OBLIGATIONS...........................................................................7
SECTION 3.01.  Redemptions Suspended During Default...............................................................7
</TABLE>

- -----------------
*This Table of Contents is not a part of the Indenture and has no bearing upon
the interpretation of its terms and provisions.

<TABLE>
<S>                                                                                                               <C>
SECTION 3.02.  Redemptions........................................................................................8
</TABLE>

                                       i


<PAGE>   18

<TABLE>
<S>                <C>                                                                                           <C> 
                   (a) Redemptions with Premium...................................................................8
                   (b) Redemptions without Premium................................................................8
                   (c) Sinking Fund Redemptions...................................................................8
                   (d) Adjustment of Redemption Payments..........................................................8
SECTION 3.03.  Terminal Mandatory Redemption......................................................................9
SECTION 3.04.  Redemptions to Comply with Provisions of
                   1104(b)(2) of the Act..........................................................................9
SECTION 3.05.  Redemption After Total Loss, Requisition
                   of Title, Seizure or Forfeiture of
                   Vessel or Termination of Certain
                   Contracts......................................................................................9
SECTION 3.06.  Redemption After Assumption by the
                   Secretary......................................................................................9
SECTION 3.07.  Determination of Obligations to be
                   Redeemed......................................................................................10
SECTION 3.08.  Notices of Redemption.............................................................................10
SECTION 3.09.  Deposit of Redemption Moneys......................................................................11
SECTION 3.10.  Payment of Redemption Price.......................................................................11

ARTICLE IV.   CASH HELD BY INDENTURE TRUSTEE OR PAYING AGENTS....................................................11
SECTION 4.01.  Generally.........................................................................................11
SECTION 4.02.  Paying Agents Other Than Indenture Trustee........................................................12
SECTION 4.03.  Unclaimed Amounts.................................................................................12
SECTION 4.04.  Application of Funds..............................................................................13

ARTICLE V.    REPRESENTATIONS AND AGREEMENTS OF SHIPOWNER........................................................13
SECTION 5.01.  Authorization, Execution and
                   Delivery of Indenture.........................................................................13
SECTION 5.02.  Payment and Procedure for Payment of
                   Obligations...................................................................................13
SECTION 5.03.  Offices or Agencies of Shipowner..................................................................13

ARTICLE VI.   INDENTURE DEFAULTS AND REMEDIES....................................................................14
SECTION 6.01.  What Constitutes "Indenture Defaults".............................................................14
SECTION 6.02.  Demand for Payment of Guarantees..................................................................14
SECTION 6.03.  Appointment of Indenture Trustee and
                   Holders of Outstanding Obligations as
                   Attorneys-in-Fact.............................................................................15
SECTION 6.04.  Termination and Payment of the Guarantees.........................................................15
SECTION 6.05.  Rights of Indenture Trustee After
                   Indenture Default.............................................................................17

SECTION 6.06.  (a) Obligees' Right to Direct Indenture
                   Trustee After Indenture Default...............................................................17
</TABLE>

                                      ii
<PAGE>   19

<TABLE>
<S>                 <C>                                                                                          <C>
                    (b) Limitations on Obligees Right to Sue.....................................................17
                    (c) Unconditional Right of Obligees to
                        Sue for Principal (and Premium, if
                        any) and Interest........................................................................18
SECTION 6.07.  Undertaking for Costs.............................................................................18
SECTION 6.08.  Recision of Payments..............................................................................19
SECTION 6.09.  Assumption of Obligations of Secretary............................................................19

ARTICLE VII.  THE INDENTURE TRUSTEE..............................................................................20
SECTION 7.01.  Acceptance of Trusts..............................................................................20
SECTION 7.02.  Eligibility of Indenture Trustee..................................................................20
SECTION 7.03.  Rights and Duties of Indenture Trustee............................................................20
SECTION 7.04.  Compensation, Expenses and Indemnification of Indenture Trustee...................................23
SECTION 7.05.  Resignation and Removal of Indenture
                    Trustee......................................................................................24
SECTION 7.06.  Appointment of Successor Indenture
                    Trustee......................................................................................24
SECTION 7.07.  Effect of Appointment of Successor
                    Indenture Trustee............................................................................24
SECTION 7.08.  Merger, Consolidation and Sale
                    of Indenture Trustee.........................................................................25

ARTICLE VIII. CONSOLIDATION, MERGER AND SALE BY SHIPOWNER........................................................25
SECTION 8.01.  Consolidation, Merger or Sale
                    by Shipowner.................................................................................25
SECTION 8.02.  Sale of Vessel by the Secretary...................................................................26

ARTICLE IX.   ACTS OF OBLIGEES...................................................................................26
SECTION 9.01.  Acts of Obligees..................................................................................27

ARTICLE X.    SUPPLEMENTAL INDENTURES............................................................................27
SECTION 10.01.  Permissible Without Action by Obligees...........................................................27
SECTION 10.02.  Protection of Indenture Trustee..................................................................28
SECTION 10.03.  Reference in Obligations
                to Supplemental Indentures.......................................................................28
SECTION 10.04.  Waivers and Supplemental Indentures
                with Consent of Obligees.........................................................................28
SECTION 10.05.  Consent of Secretary.............................................................................29
SECTION 10.06.  Continued Validity of the Guarantees.............................................................29

ARTICLE XI.   PERFORMANCE OF OBLIGATIONS TO SECRETARY............................................................30
SECTION 11.01.  Performance of Obligations to Secretary..........................................................30

ARTICLE XII.  SATISFACTION AND DISCHARGE OF INDENTURE............................................................30
</TABLE>
                                      iii
<PAGE>   20

<TABLE>
<S>                                                                                                              <C>
SECTION 12.01.  Satisfaction and Discharge
                    of Indenture.................................................................................30

ARTICLE XIII. MISCELLANEOUS......................................................................................30
SECTION 13.01.  Notices and Demands..............................................................................30
SECTION 13.02.  Waivers of Notice................................................................................31
SECTION 13.03.  Benefit of Indenture.............................................................................31
SECTION 13.04.  Execution of Counterparts........................................................................31
SECTION 13.05.  Table of Contents; Titles and Headings...........................................................31
SECTION 13.06.  Integration with Special Provisions of
                    the Indenture................................................................................31
SECTION 13.07.  Immunity of Incorporators, Stockholders,
                    Officers and Directors.......................................................................31
SECTION 13.08   Applicable Law...................................................................................32
</TABLE>

                                      iv




<PAGE>   21




                                   EXHIBIT 1

                      GENERAL PROVISIONS OF THE INDENTURE
                           INCORPORATED BY REFERENCE

                                   ARTICLE I

                      DEFINITIONS; OFFICER'S CERTIFICATES
                            AND OPINIONS OF COUNSEL

          SECTION 1.01. Definitions. For all purposes of this Indenture, the
terms used herein shall have the meanings specified in the Special Provisions
hereof, including without limitation Schedule A to this Indenture.

          SECTION 1.02. Officer's Certificates and Opinions of Counsel. (a)
Each Officer's Certificate or Opinion of Counsel with respect to compliance
with a covenant or condition provided for herein (or waiver thereof) shall
include:

               (1)  A statement that the Person or Persons making such
          certificate or rendering such opinion has or have read such covenant
          or condition;

               (2)  A brief statement as to the nature and scope of the
          examination or investigation upon which the statements or opinions
          contained in such certificate or opinion are based;

               (3)  A statement that, in the opinion of such Person or Persons,
          he or they have made or caused to be made such examination or
          investigation as is necessary to enable him or them to express an
          informed opinion as to whether or not such covenant or condition has
          been complied with (or compliance therewith has been waived); and

               (4)  A statement as to whether or not, in the opinion of such
          Person or Persons, such condition or covenant has been complied with
          (or such compliance has been waived).

         (b) An Opinion of Counsel may be based (insofar as it relates to
factual matters, information with respect to which is in the possession of any
Person) upon a certificate or opinion of or representations in writing signed
by an officer or officers of such Person or by such Person, as the case may be,
and may be based upon an Opinion of Counsel signed by another counsel.

         An Opinion of Counsel may state that said opinion is subject to the
execution and delivery of designated instruments if copies of such instruments
in form approved by such

                                       1
<PAGE>   22

counsel are delivered to the Indenture Trustee prior to or concurrently with
the delivery of said opinion.

     (c)  A certificate or opinion of a Person or Persons other than counsel
may be based, insofar as it relates to legal matters, upon an Opinion of
Counsel, unless the Person or Persons signing such certificate or opinion knew
that such Opinion of Counsel was erroneous or, in the exercise of reasonable
care, should have known that the same was erroneous.

     (d)  If the Indenture requires or permits the execution of any document by
officers, counsel or other Persons, such document may be executed in
counterparts by different officers, counsel or other Persons, all of which
shall form one instrument.

     (e)  If the signer of any document is required to be approved by the
Indenture Trustee, the acceptance of such document by the Indenture Trustee
shall be sufficient and conclusive evidence of such approval.

     (f)  The fact that the delivery of any document is a condition precedent
to any action required or permitted hereby shall not preclude the withdrawal,
revocation, rescission, modification or amendment of such document at any time
prior to such action, and, in the event of any such withdrawal, revocation or
rescission, such document shall be disregarded for all purposes of this
Indenture.

                                   ARTICLE II
                                THE OBLIGATIONS

     SECTION 2.01. Designation of Obligations. The Obligations of each series
shall be designated as stated in the Special Provisions hereof or in the
Supplemental Indenture establishing such series.

     SECTION 2.02. Issue, Form, Principal Amount, Maturity, Interest, Place of
Payment, Denominations and Redemption of Obligations. (a) Upon or after the
execution and delivery of this Indenture the aggregate principal amount of
Obligations of the series and Stated Maturity or Maturities permitted by the
Special Provisions hereof may be executed by the Shipowner, authenticated by
the Indenture Trustee, and delivered as provided herein.

     (b)  The Obligations of each series and Stated Maturity to be issued
hereunder, the Guarantees of the United States to be endorsed thereon and the
Indenture Trustee's authentication certificates to be endorsed thereon shall,
in the case of the initial series of Obligations, be in the form or forms set
forth in Exhibit 2 to the Special Provisions hereof or, in the case of
Obligations of any additional series, in the form or forms set forth in the
Supplemental Indenture establishing such series, and said Obligations shall:

          (1)  be limited to the respective principal amounts stated in the
     Special Provisions hereof or in the Supplemental Indenture
     establishing such series;

                                       2
<PAGE>   23

          (2) bear interest from the date specified in Section 2.06 at the rate
     or rates per annum stated in such Obligations;

          (3) Mature in the amount or amounts and at the time or time stated
     therein;

          (4) be payable as to principal (and any premium thereon if premium in
     case of redemption prior to Stated Maturity is provided for therein), in
     any coin or currency of the United States which at the time of payment is
     legal tender for public and private debts, at an office or agency
     maintained from time to time by the Shipowner for such purpose as provided
     in Section 5.03 at the place or places stated in the Special Provisions
     hereof and payable as to interest as aforesaid or, at the option of the
     Shipowner, by check mailed by such office or agency to the addresses of
     the Obligees as such addresses shall appear in the Obligation Register;

          (5) be issued in the denominations provided in the Special Provisions
     hereof or in the Supplemental Indenture establishing such series; and

          (6) be subject to redemption to the extent and as provided in Article


     (c) If the Maturity of any Obligation or an Interest Payment Date for any
Obligation shall be a day other than a Business Day, then such payment may be
made on the next succeeding Business Day, with the same force and effect as if
made on the nominal date for such payment, and no interest shall accrue thereon
for the period after said nominal date (whether or not such next succeeding
Business Day occurs in a succeeding month).

     SECTION 2.03. Issuance of Obligations of Initial Series. At any time and
from time to time after the execution and delivery of this Indenture, the
Shipowner may deliver to the Indenture Trustee Obligations of the initial
series issuable under this Indenture duly executed by the Shipowner as
hereinafter provided, accompanied by a Request of the Shipowner, and thereupon
the Indenture Trustee shall authenticate such Obligations, after endorsing
thereon and authenticating the Guarantees of the United States in accordance
with the Authorization Agreement, and shall deliver such Obligations and
Guarantees in accordance with such Request. Each such Request shall specify the
principal amounts, interest rates and Stated Maturities of the Obligations to
be authenticated and the names and addresses of the Persons in whose name the
Obligations are to be registered.

     SECTION 2.04. Additional Obligations; Obligations of Additional Series. At
any time or from time to time, the Shipowner may, with the approval of the
Secretary, issue additional Obligations of any series and Stated Maturity
theretofore issued or of one or more additional series, which shall (i) be in
such principal amount, and (in the case of Obligations of any additional
series) mature on such dates, bear interest at such rate or rates, be in such
form or forms and have such other terms and provisions, as shall be set forth
in a Supplemental Indenture providing for the issue thereof and (ii) be
guaranteed by the United States under Title XI of the Act pursuant to a
supplement to the Authorization Agreement.

                                       3
<PAGE>   24

     SECTION 2.05. Legends on Obligations. Any Obligation may have imprinted or
stamped thereon any legend, consistent herewith, which is prescribed by the
Shipowner and approved by the Indenture Trustee, and, except for endorsements
permitted by the second paragraph of Section 2.10(c), by the Secretary.

     SECTION 2.06. Dates of Obligations; Interest Rights. Each Obligation of
any series shall be dated the date of its authentication and except as
otherwise provided in this Section, shall bear interest from the Interest
Payment Date for Obligations of such series next preceding the date of such
Obligation to which interest on the Obligations of such series has been paid,
unless (i) the date of such Obligation is the date to which interest on the
Obligations of such series has been paid, in which case from the date of such
Obligation, or (ii) no interest has been paid on the Obligations of such series
since the original issue date (as defined below) of such Obligation, in which
case from such original issue date. The term "original issue date" of an
Obligation shall mean (a) in the case of an Obligation issued on original
issue, the date of such Obligation, or (b) in the case of an Obligation not
issued on original issue, the date of the Obligation (or portion thereof)
issued on original issue for which such Obligation was issued (directly or
indirectly) on registration of transfer, exchange or substitution.

     SECTION 2.07. Execution of Obligations. The Obligations shall from time to
time be executed on behalf of the Shipowner by a Responsible Officer thereof
(whose signature may be a facsimile), and its corporate seal (which may be a
facsimile) shall be affixed thereto or imprinted thereon and attested by its
secretary, an assistant secretary or an assistant trust officer (whose
signature may be a facsimile).

     If any officer of the Shipowner whose signature (facsimile or otherwise)
appears on any Obligation shall cease to be such officer before such Obligation
shall have been authenticated by the Indenture Trustee or delivered, such
Obligation nevertheless may be authenticated, issued and delivered with the
same force and effect as though the person or persons whose signature or
signatures (facsimile or otherwise) appear on such Obligation had not ceased to
be such officer or officers of the Shipowner.

     SECTION 2.08. Authentication of Obligations and Guarantees. No Obligation
or the Guarantee of the United States thereon shall be valid unless such
Obligation shall bear thereon an authentication certificate, manually executed
by the Indenture Trustee in accordance with the terms and conditions of the
Authorization Agreement, substantially in the form or forms referred to in
Section 2.02(b). Such authentication certificate, so executed, on any
Obligation shall be conclusive evidence, and the only competent evidence, that
such Obligation and such Guarantee have been duly executed, authenticated and
delivered hereunder.

     SECTION 2.09. Temporary Obligations. There may be issued from time to time
in lieu of (or in exchange for) any definitive Obligation or Obligations one or
more temporary Obligations of like series and Stated Maturity, with a Guarantee
of the United States endorsed thereon and authenticated by the Indenture
Trustee, substantially of the same tenor as the definitive Obligations in lieu
of (or in exchange for) which they are issued, with or without the

                                       4


<PAGE>   25

specification of any Redemption Price or Prices. Such temporary Obligation or
Obligations may be in such authorized denomination or denominations as shall be
stated in a Request of the Shipowner delivered to the Indenture Trustee prior
to the authentication thereof, which Request shall specify the aggregate
principal amounts and the series and Stated Maturities of such temporary
Obligations.

     If definitive Obligations are not ready for delivery, the Holder of any
temporary Obligation may, at the Corporate Trust Office, with the consent of
the Shipowner, exchange the same for a temporary Obligation or Obligations of
like series, tenor, interest accrual date and Stated Maturity of authorized
denominations for the same aggregate principal amount upon the surrender for
cancellation of such temporary Obligation or Obligations.

     When definitive Obligations are ready for delivery, the Holder of any
temporary Obligation may, at the Corporate Trust Office, exchange the same
without charge for a definitive Obligation or Obligations of like series,
tenor, interest accrual date and Stated Maturity of authorized denominations
for the same aggregate principal amount.

     SECTION 2.10. Registration, Transfer and Exchange. (a) The Shipowner shall
cause the Indenture Trustee to keep an Obligation Register for the registration
of ownership, transfers and exchanges of Obligations, at the Corporate Trust
Office.

     (b) Any Obligation may be transferred at the Corporate Trust Office, by
surrender of such Obligation for cancellation, accompanied by an instrument of
transfer in form satisfactory to the Shipowner and the Indenture Trustee, duly
executed by the registered Obligee or his duly authorized attorney, and
thereupon the Shipowner shall execute, and the Indenture Trustee shall
authenticate and deliver in the name of the transferee or transferees, a new
Obligation or Obligations, and the Guarantee or Guarantees of the United States
thereon, in authorized denominations of like series, tenor, interest accrual
date and Stated Maturity and for the same aggregate principal amount.

     (c) The Shipowner shall not be required to register transfers or make
exchanges of (1) Obligations for a period of 15 days immediately prior to (A)
an Interest Payment Date or (B) any selection of Obligations to be redeemed,
(2) Obligations after demand for payment of the Guarantees and prior to the
payment thereof or rescission of such demand pursuant to Section 6.02(a), or
(3) any Obligation which has been selected for redemption in whole or in part.

     If any Obligation surrendered for transfer or exchange has been selected
for redemption in whole or in part, there may be endorsed on any Obligation or
Obligations issued therefor an appropriate notation of such fact.

     (d) Any Obligation shall be exchangeable for a like principal amount of
Obligations of the same series, tenor, interest accrual date and Stated
Maturity but of different authorized denominations. Obligations to be exchanged
shall be surrendered at the Corporate Trust Office, and the Shipowner shall
execute, and the Indenture Trustee shall authenticate and deliver in

                                       5
                                                                             
<PAGE>   26

exchange therefor, the Obligation or Obligations, and the Guarantee or
Guarantees of the United States thereon, requested by the Obligee in accordance
with this paragraph (d).

     (e) As a condition precedent to any transfer or exchange of Obligations,
the Shipowner may (except upon an exchange of temporary for definitive
Obligations) require the payment of a sum sufficient to reimburse it for any
taxes or other governmental charges that may be imposed with respect thereto
and a sum not exceeding $2.00 for each Obligation delivered upon any such
transfer or exchange.

     SECTION 2.11. Who Treated as Owners. The Shipowner, the Indenture Trustee,
the Secretary, and any office or agency for the payment of principal of (and
premium, if any) or interest on the Obligations may deem and treat the Person
in whose name any Obligation is registered in the Obligation Register as the
absolute owner of such Obligation for all purposes, and neither the Shipowner,
the Indenture Trustee, the Secretary, nor any such office or agency shall be
affected by any notice to the contrary, whether such Obligation shall be past
due or not. All payments of or on account of principal (and premium, if any) or
interest, or pursuant to the Guarantee endorsed on such Obligation, to such
registered Obligee shall be valid and effectual to satisfy and discharge the
liability of the Shipowner and the Secretary to the extent of the sum or sums
so paid, except as otherwise provided in Section 6.08.

     SECTION 2.12. Lost, Stolen, Destroyed or Mutilated Obligations. Upon
receipt by the Shipowner and the Indenture Trustee of evidence satisfactory to
them of the loss, theft, destruction or mutilation of any Outstanding
Obligation and the ownership thereof, the Shipowner may execute, and upon
request of the Shipowner, the Indenture Trustee shall, but subject to all
limitations imposed by the Authorization Agreement and only to the extent
authorized thereby, authenticate and deliver, a new Obligation, and the
Guarantee of the United States thereon, of like series, tenor, interest accrual
date, principal amount and Stated Maturity (which may bear such notation as may
be required by the Indenture Trustee or by usage or by the rules of any stock
exchange upon which the Obligations are then listed and which shall bear a
serial number different from the serial number of the lost, stolen, destroyed
or mutilated Obligation) in lieu of such lost, stolen, destroyed or mutilated
Obligation and, similarly, upon receipt by the Shipowner and the Indenture
Trustee of evidence satisfactory to them of the loss, theft, destruction or
mutilation of any Obligation which has or is about to become due and payable,
the Indenture Trustee may deem the applicant with respect thereto to be the
owner of said Obligation for the purpose of receiving payment on account
thereof of principal (and premium, if any) upon maturity or interest or the
payment of the Guarantee thereof; provided that, as conditions precedent to the
execution, authentication and delivery of any new Obligation in place of said
Obligation or to any payment contemplated by this Section, (1) the Shipowner,
the Indenture Trustee and the Secretary shall receive indemnity satisfactory to
the Shipowner, the Indenture Trustee and the Secretary, (2) the Shipowner shall
be reimbursed for all reasonable expenses (including any fees or expenses of
the Indenture Trustee) incident thereto, and (3) said Obligation shall (unless
the same shall have been lost, stolen or destroyed) be surrendered.

                                       6
 

<PAGE>   27
     Obligations issued pursuant to this Section and the Guarantees endorsed
thereon shall constitute original contractual obligations of the Shipowner and
the United States, respectively, whether or not the lost, stolen or destroyed
Obligations be at any time enforceable by anyone, and shall be equally and
proportionately entitled to the benefits of this Indenture with all other
Outstanding Obligations issued hereunder.

     The provisions of this Section 2.12 are exclusive and shall preclude (to
the extent lawful) all other rights and remedies with respect to the
replacement or payment of lost, stolen, destroyed or mutilated Obligations.

     SECTION 2.13. Reacquired Obligations; Cancellation and Disposition of
Obligations. In the event the Shipowner shall reacquire any Obligations
(whether by purchase or otherwise), such Obligations shall forthwith be
delivered to the Indenture Trustee for cancellation. Except as provided in
Section 3.09(b), all Obligations surrendered for the purpose of payment,
redemption, transfer, exchange, or substitution, or (if permitted in the
Special Provisions hereof or the Supplemental Indenture establishing any
additional series of Obligations) in discharge in whole or in part of any
sinking fund payment shall, if surrendered to the Shipowner or any Paying
Agent, be delivered to the Indenture Trustee for cancellation, or, if
surrendered to the Indenture Trustee, shall be cancelled by it. No Obligation
shall be authenticated in lieu of or in exchange for any Obligation cancelled
as provided in this Section, except as may be expressly permitted by this
Indenture. Obligations cancelled by the Indenture Trustee shall be delivered or
disposed of as directed by a Request of the Shipowner.

                                  ARTICLE III

                           REDEMPTION OF OBLIGATIONS

     SECTION 3.01. Redemptions Suspended During Default. Notwithstanding the
following provisions of this Article III, neither the Shipowner nor the
Indenture Trustee shall redeem any Obligations, except pursuant to Section 3.04
or 3.06 during the continuance of any Indenture Default or event which with the
lapse of time could constitute a Payment Default, except that, where the
mailing of notice of redemption of any Obligations shall have theretofore been
made, the Indenture

                                      7


<PAGE>   1


                                                            EXHIBIT 10.8.2


                              CUSIP No. 892782 AA1

                     Forms of Bond, Guarantee and Trustee's
                           Authentication Certificate

$ 10,515,000.00                                                        No. 1


                      UNITED STATES GOVERNMENT GUARANTEED
                        SHIP FINANCING BOND, 1997 SERIES

                 7.07% Sinking Fund Bond Due September 30, 2022

                                   Issued by

                              TRAILER BRIDGE, INC.

         Principal and interest guaranteed under Title XI of the Merchant
Marine Act, 1936, as amended.

         Trailer Bridge, Inc., a Delaware corporation (herein called the
"Shipowner"), FOR VALUE RECEIVED, promises to pay to Pitney Bowes Credit
Corporation or registered assigns, the principal sum of TEN MILLION FIVE
HUNDRED FIFTEEN THOUSAND AND NO/100 DOLLARS ($10,515,000.00) on September 30,
2022, and to pay interest semiannually on March 30 and September 30 of each
year, commencing September 30, 1997, on the unpaid principal amount of this
Bond at the rate of 7.07% per annum (calculated on the basis of a 360-day year
of twelve 30-day months) from the interest payment date referred to above next
preceding the date of this Bond to which interest on the Bonds has been paid
(unless the date hereof is the date to which interest on the Bonds has been
paid, in which case from the date of this Bond), or if no interest has been
paid on the Bonds since the original issue date (as defined in the Indenture
hereinafter mentioned) of this Bond, from such original issue date, until
payment of said principal sum has been made or duly provided for, and at the
same rate per annum on any overdue principal.

         The principal of and the interest on this Bond, as well as any premium
hereon in case of certain redemptions hereof prior to maturity, are payable to
the registered owner hereof at the Corporate Trust Office of State Street Bank
and Trust Company, a Massachusetts trust company, as Indenture Trustee
(together with its successors, the "Indenture Trustee") or at the offices or
agencies which may be maintained from time to time by the Shipowner for such
purposes in any coin or currency of the United States of America which at the
time of payment is legal tender for the payment of public and private debts
therein; provided that, interest may be paid at the option of the Shipowner by
check mailed to the address of the registered owner hereof as such address


<PAGE>   2



shall appear on the Obligation Register of said Indenture Trustee, and provided
further, that the Shipowner and the registered owner hereof may enter into
other arrangements as to payment in accordance with the Special Provisions of
the Indenture (as defined below).

         This Bond is one of an issue of bonds of the Shipowner of $10,515,000
aggregate principal amount of sinking fund bonds, designated as its "United
States Government Guaranteed Ship Financing Bonds, 1997 Series", all issued
under a Trust Indenture dated as of June 23, 1997 (said Trust Indenture, as the
same may be amended, modified or supplemented from time to time as permitted
thereunder, herein called the "Indenture"), between the Shipowner and the
Indenture Trustee to aid in financing the cost of the construction by the
Shipowner of the Vessels (as defined in the Indenture). Reference is hereby
made to the Indenture for definition of certain terms used herein and a
description of the rights, limitations of rights, obligations, duties and
immunities thereunder of the Shipowner and the Indenture Trustee and the rights
and limitations of rights of the Holders of the Bonds.

         In accordance with the terms of an Authorization Agreement, dated as
of June 23, 1997 (herein the "Authorization Agreement"), between the United
States of America, represented by the Secretary of Transportation, acting by
and through the Maritime Administrator (herein called the "Secretary"), and the
Indenture Trustee, and by endorsement of the guarantee of the United States of
America (herein collectively called the "Guarantees") on each of the Bonds and
the authentication and delivery of the Guarantees by the Indenture Trustee, all
pursuant to Title XI of the Merchant Marine Act, 1936, as amended, and in
effect on June 23, 1997 (herein called the "Act"), the Bonds are guaranteed by
the United States of America as provided in the Authorization Agreement and in
the Guarantees endorsed thereon. Reference is hereby made to the Authorization
Agreement for a description of the rights, limitations of rights, obligations,
duties and immunities thereunder of the Secretary and the Indenture Trustee and
the rights and limitations of rights of the Holders of the Bonds.

         Section 1103(d) of Title XI of the Act provides that:

                       "The full faith and credit of the United States is
                       pledged to the payment of all guarantees made under this
                       title with respect to both principal and interest,
                       including interest, as may be provided for in the
                       guarantee, accruing between the date of default under a
                       guaranteed obligation and the payment in full of the
                       guarantee."

         If an Indenture Default (defined in Section 6.01 of Exhibit 1 to the
Indenture as a Payment Default, or the giving of a Secretary's Notice) shall
have occurred and be continuing, the Indenture Trustee, as provided in the
Indenture shall, not later than 60 days from the date of such Indenture
Default, demand payment by the Secretary of the Guarantees, whereupon the
entire unpaid principal amount of the Outstanding Bonds and all unpaid interest
thereon shall become due and payable on the first to occur of the date which is
30 days from the date of such demand or the date on which the Secretary pays
the Guarantees. If no demand for payment of the



                                       2
<PAGE>   3



Guarantees shall have been made by the Indenture Trustee on or before the 30th
day following an Indenture Default, the Holder of any Outstanding Bond may, in
the manner provided in the Indenture, make such demand in place of the
Indenture Trustee. In the event of an Indenture Default of which the Secretary
has actual knowledge, the Secretary, as provided in the Authorization
Agreement, will publish notice in the Authorized Newspapers, which shall
include The Wall Street Journal (all editions) and The Journal of Commerce, of
the occurrence of such Indenture Default within 30 days from the date of such
Indenture Default, unless demand for payment under the Guarantees shall
previously have been made by the Indenture Trustee, but any failure to publish
such notice or any defect therein shall not affect in any way any rights of the
Indenture Trustee or any Holder of a Bond with respect to such Indenture
Default.

         Within 30 days from the date of any demand for payment of the
Guarantees, the Secretary shall pay to the Indenture Trustee, as agent and
attorney-in-fact for the Holders of the Outstanding Bonds (including this
Bond), all the unpaid interest to the date of such payment on, and the unpaid
balance of the principal of such Bonds in full, in cash; provided that, in the
case of a demand made as a result of a Payment Default, the Secretary shall not
be required to make any such payment if within such 30-day period (and prior to
any payment of the Guarantees by the Secretary), the Secretary finds either
that there was no Payment Default, or that such Payment Default was remedied
prior to the demand for payment of the Guarantees, in which event the
Guarantees shall continue in full force and effect.

         The Holder of this Bond, by the purchase and acceptance hereof, hereby
irrevocably appoints the Indenture Trustee and each other Holder of any
Outstanding Bond as agent and attorney-in-fact for the purpose of making any
demand for payment of the Guarantees, and (in the case of the Indenture
Trustee) of receiving and distributing such payment; provided that, no action
or failure to act by the Indenture Trustee shall affect the right of the Holder
of this Bond to take any action whatsoever permitted by law and not in
violation of the terms of this Bond or of the Indenture.

         In the event of (a) a default, continued for 25 days, in the payment
of the principal of or interest on the Bonds (including this Bond) when due, or
(b) any default under the security agreement, the mortgage or any loan
agreement relating to the Obligations between the Secretary, the Shipowner and
any other parties, the Secretary shall have the right to and may, in its sole
discretion by written notice given to the Indenture Trustee on or after said
25-day period or after such default but prior to receipt by the Secretary of a
demand in accordance with the Indenture for payment under the Guarantees,
assume all of the rights and obligations of the Shipowner under the Indenture
and the Bonds, and if such default relates to the payment of the principal of
and interest on the Bonds, make all payments then in default under the Bonds.

         Any amount payable by the Secretary under the Guarantees shall not be
subject to any claim or defense of the United States of America, the Secretary,
or others, whether by way of counterclaim, set-off, reduction or otherwise.
Further, the Holder of this Bond shall have no right, title or interest in any
collateral or security given by the Shipowner to the Secretary.



                                       3
<PAGE>   4



         After payment of the Guarantees by the Secretary to the Indenture
Trustee, this Bond (1) if it has not then been surrendered for cancellation or
canceled, shall represent only the right to receive payment in cash of an
amount (less the amount, if any, required to be withheld with respect to
transfer or other taxes on payments to the Holder of this Bond) equal to the
unpaid principal amount hereof and the unpaid interest accrued hereon to the
date on which the Secretary shall have paid the Guarantees in full in cash to
the Indenture Trustee, (2) shall otherwise no longer constitute or represent an
obligation of the Shipowner, and (3) shall not be entitled to any other rights
or benefits provided in the Indenture, subject to Section 6.08 of the
Indenture.

         The Bonds (including this Bond) may be redeemed upon the terms and
conditions provided in the Indenture, in whole (but not in part), at the option
of the Shipowner, at any time upon at least 30 and not more than 60 days prior
notice given as provided in the Indenture, at a Redemption Price equal to 100%
of the principal amount thereof plus the Redemption Premium plus interest
accrued thereon to the date of redemption; provided that, no such redemption
shall be made prior to March 30, 2008, directly or indirectly, with the
proceeds of, or in anticipation of, borrowing by or for the account of the
Shipowner if such borrowing has an effective interest cost (calculated in
accordance with generally accepted financial practice) of less than the rate
borne by the Bonds.

         "Redemption Premium" applicable in respect of any redemption of the
Bonds pursuant to Article Third (c) of the Indenture shall mean the greater of
(a) zero and (b) the excess of:

     (i) the sum of the respective present values as of the date such
         Redemption Premium becomes due and payable of: (A) the pro rata
         portion of each payment of a scheduled installment of principal that
         would have been required to be made with respect to the principal
         amount of the Bonds being redeemed (the "Prepaid Principal") during
         the remaining term to maturity of the Bonds, (B) without duplication,
         the pro rata portion of the payment of the principal balance that
         would have been required to be made at final maturity of the Bonds
         with respect to such Prepaid Principal, and (C) each payment of
         interest that would have been required to be paid during the remaining
         term to maturity of the Bonds with respect to such Prepaid Principal
         determined, in the case of each such required principal payment prior
         to maturity, principal payment at final maturity and interest payment,
         by discounting the amount thereof (on a semiannual basis) from the
         date fixed therefor back to the date such Redemption Premium becomes
         due and payable at the Reference Rate (as hereinafter defined)
         (assuming for such purpose that all such payments were made when due
         pursuant to the terms of the Bonds and the Indenture, and that no
         other payment with respect to such Prepaid Principal was made) over

    (ii) the amount of such Prepaid Principal.

         "Reference Rate" applicable in respect of any Bond shall mean a per 
annum rate equal to



                                       4
<PAGE>   5



         the annual yield for United States Treasury securities having a term
         to maturity equal to the remaining weighted average life to maturity
         (calculated in accordance with customary United States investment
         banking practices) of the Bonds as such annual yield is determined by
         reference to Federal Reserve Statistical Release H.15 (519) ("Release
         H.15") published most recently prior to the third Business Day
         preceding the date such amount becomes due and payable, or if Release
         H.15 is no longer published, such annual yield as determined, at the
         expense of the Shipowner, by such other publication or source of
         information selected by the Shipowner and acceptable to the Indenture
         Trustee and all Holders, provided that, if there shall be no actual
         United States Treasury security having a term to maturity equal to the
         remaining weighted average life to maturity of the Bonds, the annual
         yield for a United States Treasury security deemed to have such a term
         to maturity shall be linearly interpolated on a basis consistent with
         the actual yields of other United States Treasury securities as
         determined by reference to Release H.15, or (if Release H.15 is no
         longer published) as determined at the expense of the Shipowner by
         such other publication or source of information.

         The Bonds (including this Bond) are also subject to redemption, upon
the terms and conditions provided in the Indenture and upon like notice,
through the operation of a mandatory sinking fund providing for the redemption
on March 30, 1998, and on each September 30 and March 30 thereafter to and
including September 30, 2022, at 100% of the principal amount thereof plus
interest accrued thereon to such date, of a principal amount of such Bonds
equal to $210,300 and on September 30, 2022, the entire unpaid principal amount
of the Outstanding Bonds shall be paid in full, together with all interest
accrued thereon to such date, provided that, notwithstanding the foregoing
provisions of this paragraph, in case the principal amount of Outstanding Bonds
shall be reduced by reason of any redemption described in the next succeeding
paragraph, the principal amount of Bonds to be redeemed through the operation
of the mandatory sinking fund on each subsequent mandatory sinking fund
redemption date shall be subject to reduction as provided in the Indenture. In
lieu of making all or any part of any such mandatory sinking fund redemption,
the Shipowner may, at its option, receive credit for Bonds (not previously so
credited or applied to reduce the amount of Bonds outstanding) (i) redeemed
pursuant to the optional redemption at a premium referred to above, or (ii)
purchased or acquired by the Shipowner other than by redemption. Bonds so
credited shall be credited by the Indenture Trustee at 100% of the principal
amount thereof.

         The Bonds (including this Bond) are also subject to redemption, upon
the terms and conditions provided in the Indenture, in whole or in part, at
100% of the principal amount thereof, plus interest accrued thereon to the date
of redemption, upon at least 30 and not more than 60 days prior notice (a) in
the event that Bonds must be redeemed so that the principal amount of all
Obligations Outstanding after such redemption will not exceed 87 1/2% of the
Depreciated Actual Cost or Actual Cost, as the case may be, of the Vessels, as
determined by the Secretary, (b) in the event of an actual, constructive,
agreed or compromised total loss of, or requisition of title to, or seizure or
forfeiture of, a Vessel or Vessels, (c) in the event of termination of a
contract relating to the construction of a Vessel, or (d) in the event that,
after an



                                       5
<PAGE>   6



assumption by the Secretary of the Bonds, a purchaser of a Vessel or Vessels
from the Secretary does not assume all the rights and obligations of the
Shipowner under the Indenture relating to such Vessel or Vessels.

         The Bonds (including this Bond) may also be redeemed upon the terms
and conditions provided in the Indenture, in whole or in part, at the option of
the Secretary, at any time following an assumption of the Bonds and the
Indenture by the Secretary and prior to any sale of a Vessel or Vessels to a
purchaser which assumes the Shipowner's rights and obligations under the Bonds
and the Indenture, upon at least 30 and not more than 60 days prior notice
given as provided in the Indenture, at a Redemption Price equal to 100% of the
principal amount to be redeemed, plus interest accrued to the date fixed for
redemption.

         Any optional redemption shall be subject to the receipt of the
redemption moneys by the Indenture Trustee or any Paying Agent. Bonds called
for redemption shall (unless the Shipowner shall default in the payment of such
Bonds at the applicable Redemption Price plus accrued interest) cease to bear
interest on and after the date fixed for redemption.

         As provided in the Indenture and to the extent permitted thereby,
compliance by the Shipowner with any of the terms of the Indenture may be
waived, and the Indenture and the rights and obligations of the Shipowner, and
the rights of the Holders of the Bonds (including this Bond) thereunder may be
modified, at any time with the prior consent of the Secretary, and except as
otherwise expressly provided in the Indenture, the consent of the Holders of at
least 60% in principal amount of the Outstanding Bonds affected thereby in the
manner and subject to the limitations set forth in the Indenture; provided
that, no such waiver or modification shall (1) without the consent of the
Holder of each Bond affected thereby: (a) change the Stated Maturity or reduce
the principal amount of any Bond, (b) extend the time of payment of, or reduce
the rate of, interest thereon, (c) change the due date of or reduce the amount
of any sinking fund payment, (d) reduce any premium payable upon the redemption
thereof, or (e) change the coin or currency in which any Bond or the interest
thereon is payable; or (2) without the consent of all Holders of Bonds: (a)
terminate or modify any of the Guarantees or the obligations of the United
States of America thereunder, (b) reduce the amount of any of the Guarantees,
(c) eliminate, modify or condition the duties of the Indenture Trustee to
demand payment of the Guarantees, (d) eliminate or reduce the eligibility
requirements of the Indenture Trustee, or (e) reduce the percentage of
principal amount of Bonds the consent of whose Holders is required for any such
modification or waiver.

         The Indenture provides that the Bonds (including this Bond) shall no
longer be entitled to any benefit provided therein if the Bonds shall have
become due and payable at Maturity (whether by redemption or otherwise) and
funds sufficient for the payment thereof (including interest to the date fixed
for such payment, together with any premium thereon) and available for such
payment (1) shall be held by the Indenture Trustee or any Paying Agent, or (2)
shall have been so held and shall thereafter have been paid to the Shipowner
after having been unclaimed for 6 years after the date of maturity thereof
(whether by redemption or otherwise) or the date of



                                       6
<PAGE>   7



payment of the Guarantees, except for the right (if any), of the Holder to
receive payment from the Shipowner of any amounts paid to the Shipowner as
provided in (2) above with respect to this Bond, all subject to the provisions
of Section 6.08 of Exhibit 1 to the Indenture.

         The transfer of this Bond may be registered by the registered Holder
or by his duly authorized attorney, at the Corporate Trust Office of the
Indenture Trustee, upon surrender or cancellation of this Bond, accompanied by
an instrument of transfer in form satisfactory to the Shipowner and the
Indenture Trustee, duly executed by the registered Holder hereof or his
attorney duly authorized in writing, and thereupon a new, fully registered Bond
or Bonds of like series and maturity for the same aggregate principal amount
will be issued to the transferee in exchange therefor, each in the principal
amount of $1,000 or any integral multiple thereof, subject to the provisions of
the Indenture. The Indenture provides that the Shipowner shall not be required
to make transfers or exchanges of (1) Bonds for a period of 15 days immediately
prior to an Interest Payment Date, (2) Bonds after demand for payment of the
Guarantees and prior to payment thereof or rescission of such demand as
provided in Section 6.02(a) of Exhibit 1 to the Indenture, or (3) any Bond
which has been selected for redemption in whole or in part.

         The Shipowner, the Secretary, the Indenture Trustee and any office or
agency for the payment of Bonds may deem and treat the person in whose name
this Bond is registered as the absolute owner thereof for all purposes, and
neither the Shipowner, the Secretary, the Indenture Trustee, nor any such
office or agency shall be affected by any notice to the contrary, whether this
Bond shall be past due or not.

         No recourse shall be had for the payment of principal of, or the
interest or premium (if any) on, this Bond, or for any claim based hereon or on
the Indenture, against any incorporator or any past, present or future
subscriber to the capital stock, stockholder, officer or director of the
Shipowner or of any successor corporation, as such, either directly or through
the Shipowner or any such successor corporation, under any constitution,
statute or rule of law or by the enforcement of any assessment, or otherwise,
all such liability being expressly waived and released by the acceptance of
this Bond and by the terms of the Indenture.

         Neither this Bond nor the Guarantee endorsed hereon shall be valid or
become obligatory for any purpose until the Indenture Trustee shall have fully
signed the authentication certificate endorsed hereon.



                                       7
<PAGE>   8





         IN WITNESS WHEREOF, the Shipowner has caused this Bond to be duly
executed by the manual or facsimile signatures of its duly authorized officers
under its corporate seal or facsimile thereof.

Dated as of June 23, 1997                             TRAILER BRIDGE, INC.

(SEAL)

                                                      BY: John McCown
                                                          -----------
                                                          Chairman

Attest:



William G. Gotimer, Jr.
- -----------------------



                                       8
<PAGE>   9





                   GUARANTEE OF THE UNITED STATES OF AMERICA

         The United States of America, represented by the Secretary of
Transportation, acting by and through the Maritime Administrator, pursuant to
Title XI of the Merchant Marine Act, 1936, as amended, hereby guarantees to the
holder of the within Bond, upon demand of the holder or his agent, payment of
the unpaid interest on, and the unpaid balance of the principal of, such Bond,
including interest accruing between the date of default under such Bond and the
payment in full of this Guarantee. The full faith and credit of the United
States of America is pledged to the payment of this Guarantee. The validity of
this Guarantee is incontestable in the hands of any holder of such Bond.
Payment of this Guarantee will be made in accordance with the provisions of
such Bond.

                                                    UNITED STATES OF AMERICA
                                                    SECRETARY OF TRANSPORTATION

(SEAL OF THE DEPARTMENT
     OF TRANSPORTATION)

                                                     BY: A. J. Herberyer
                                                         ---------------
                                                         Maritime Administrator

                      TRUSTEE'S AUTHENTICATION CERTIFICATE

         This is one of the Bonds described in the Indenture and the foregoing
Guarantee is one of the Guarantees described in the Authorization Agreement.

                                                     STATE STREET BANK AND
                                                     TRUST COMPANY, Indenture
                                                     Trustee

                                                     By: Gerald Wheeler
                                                         --------------
                                                         Authorized Officer



                                       9
<PAGE>   10


                                    PAYMENTS ON ACCOUNT OF PRINCIPAL

                      Amount of                  Balance of           Authorized
Payment Date          Principal Paid             Principal Unpaid     Signature



                                      10


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