AMENDMENT NO. 7 TO
LOAN AND SECURITY AGREEMENT

        AMENDMENT NO. 7 TO LOAN AND SECURITY AGREEMENT (“Amendment No. 7”) dated
as of March 20, 2008, by and among Wachovia Bank, National Association,
successor by merger to Congress Financial Corporation (Florida), in its capacity
as agent pursuant to the Loan Agreement (as hereinafter defined) acting for and
on behalf of the financial institutions which are parties thereto as lenders (in
such capacity, “Agent”), the financial institutions which are parties to the
Loan Agreement as lenders (individually, each a “Lender” and collectively,
“Lenders”) and Trailer Bridge, Inc. (“Borrower”).

W I T N E S S E T H :

        WHEREAS, Agent, Lenders and Borrower have entered into financing
arrangements pursuant to which Lenders (or Agent on behalf of Lenders) have made
and may make loans and advances and provide other financial accommodations to
Borrower as set forth in the Loan and Security Agreement, dated April 23, 2004,
by and among Agent, Lenders and Borrower, as amended by Amendment No. 1 to Loan
and Security Agreement, dated as of September 10, 2004, Amendment No. 2 to Loan
and Security Agreement, dated as of December 1, 2004, Amendment No. 3 to Loan
and Security Agreement, dated as of December 22, 2004, Amendment No. 4 and
Waiver to Loan and Security Agreement, dated as of November 1, 2006, Amendment
No. 5 to Loan and Security Agreement, dated April 23, 2007 and Amendment No. 6
to Loan and Security Agreement, dated as of June 14, 2007 (as the same now
exists and may hereafter be amended, modified, supplemented, extended, renewed,
restated or replaced the “Loan Agreement”), and the other agreements, documents
and instruments referred to therein or at any time executed and/or delivered in
connection therewith or related thereto, including, but not limited to, this
Amendment No. 7 (all of the foregoing, together with the Loan Agreement, as the
same now exist or may hereafter be amended, modified, supplemented, extended,
renewed, restated or replaced, being collectively referred to herein as the
“Financing Agreements”);

        WHEREAS, Borrower used cash to purchase additional equipment in 2007 in
order to expand its market into the Dominican Republic (the “Dominican Republic
Expansion”);

        WHEREAS, an Event of Default has occurred under Section 10.1(a)(iii) of
the Loan Agreement as a result of the failure of Borrower to maintain the Fixed
Charge Coverage Ratio required under Section 9.17(a) of the Loan Agreement for
the period ended December 31, 2007 (the “FCCR Default”);

        WHEREAS, Borrower has requested that Agent and Lenders agree to amend
the Loan Agreement and Agent and Lenders are agreeable to such requests, but
only on the terms and subject to the conditions contained herein; and

        WHEREAS, by this Amendment No. 7, Agent, Lenders, and Borrower wish and
intend to evidence such amendments.

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

        1.     Definitions.

                1.1      Additional Definitions. As used herein, the following
terms shall have the respective meanings given to them below and the Loan
Agreement and the other Financing Agreements are hereby amended to include, in
addition and not in limitation, the following definitions:

  “Amendment No. 7” shall mean Amendment No. 7 to Loan and Security Agreement,
dated as of June 14, 2007, by and among Borrower, Agent and Lenders, as the same
now exists and may hereafter be amended, modified, supplemented, extended,
renewed, restated or replaced.

                1.2      Interpretation. Capitalized terms used herein which are
not otherwise defined herein shall have the respective meanings ascribed to them
in the Loan Agreement.

        2.     Fixed Charge Coverage Ratio. Section 9.17(a) of the Loan
Agreement is hereby amended by deleting such Section in its entirety and
substituting the following therefor:

  “(a) Without giving effect to the capital expenditures of Borrower in the
aggregate amount of up to $17,673,290 incurred during the period from January 1,
2007 through and including December 31, 2007 in connection with the Dominican
Republic Expansion, the Fixed Charge Coverage Ratio of Borrower for each period
of twelve fiscal months ending on the last day of each fiscal quarter, beginning
with the fiscal quarter ending on March 31, 2008, shall not be less than
1.0:1.0.”

        3.     Additional Representations, Warranties and Covenants. Borrower
represents, warrants and covenants with and to Agent and Lenders as follows,
which representations, warranties and covenants are continuing and shall survive
the execution and delivery hereof, the truth and accuracy of, or compliance with
each, together with the representations, warranties and covenants in the other
Financing Agreements, being a continuing condition of the making of Loans by
Lenders (or Agent on behalf of Lenders) to Borrower:

                3.1      Neither the execution, delivery and performance of this
Amendment No. 7, or any other Financing Agreements in connection herewith, nor
the consummation of the transactions herein or therein contemplated, are in
contravention of law or any indenture, agreement or undertaking to which
Borrower is a party or by which Borrower or its property are bound, or violates
any provision of the Certificate of Incorporation or By-Laws (or similar
governing documents) of Borrower;

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                3.2      No consent, approval or other action of, or filing
with, or notice to any Governmental Authority is required in connection with the
execution, delivery and performance of this Amendment No. 7;

                3.3      This Amendment No. 7 has been duly executed and
delivered by Borrower and the agreements and obligations of Borrower contained
herein constitute legal, valid and binding obligations of Borrower enforceable
against Borrower in accordance with their respective terms;

                3.4      All of the representations and warranties set forth in
the Loan Agreement and the other Financing Agreements, each as amended hereby,
are true and correct in all material respects on and as of the date hereof as if
made on the date hereof, except to the extent any such representation or
warranty is made as of a specified date, in which case such representation or
warranty shall have been true and correct in all material respects as of such
date; and

                3.5      No Default or Event of Default exists or has occurred
and is continuing.

        4.     Conditions Precedent.

                4.1      Agent shall have received an executed original or
executed counterparts of this Amendment No. 7, duly authorized, executed and
delivered by each of the respective parties hereto;

                4.2      Agent shall have received an Affidavit of Execution and
Delivery, in form and substance satisfactory to Agent, duly authorized, executed
and delivered by Borrower; and

                4.3      No Default or Event of Default shall exist or have
occurred and be continuing.

        5.     Effect of this Amendment. This Amendment No. 7 constitutes the
entire agreement of the parties with respect to the subject matter hereof and
thereof, and supersedes all prior oral or written communications, memoranda,
proposals, negotiations, discussions, term sheets and commitments with respect
to the subject matter hereof and thereof. Except as expressly amended pursuant
hereto, no other changes or modifications to the Financing Agreements are
intended or implied, and in all other respects the Financing Agreements are
hereby specifically ratified, restated and confirmed by all parties hereto as of
the effective date hereof. To the extent that any provision of the Loan
Agreement or any of the other Financing Agreements are inconsistent with the
provisions of this Amendment, the provisions of this Amendment shall control.

        6.     Further Assurances. Borrower shall execute and deliver such
additional documents and take such additional action as may be requested by
Agent to effectuate the provisions and purposes of this Amendment No. 7.

        7.     Governing Law. The rights and obligations hereunder of each of
the parties hereto shall be governed by and interpreted and determined in
accordance with the internal laws of the State of Florida but excluding any
principles of conflicts of law or other rule of law that would cause the
application of the law of any jurisdiction other than the laws of the State of
Florida.

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        8.     Binding Effect. This Amendment No. 7 shall be binding upon and
inure to the benefit of each of the parties hereto and their respective
successors and assigns.

        9.     Counterparts. This Amendment No. 7 may be executed in any number
of counterparts, but all of such counterparts shall together constitute but one
and the same agreement. In making proof of this Amendment No. 7, it shall not be
necessary to produce or account for more than one counterpart thereof signed by
each of the parties hereto. Delivery of an executed counterpart of this
Amendment No. 7 by telecopier or other electronic method of transmission shall
have the same force and effect as delivery of an original executed counterpart
of this Amendment No. 7. Any party delivering an executed counterpart of this
Amendment No. 7 by telecopier or other electronic method of transmission also
shall deliver an original executed counterpart of this Amendment No. 7, but the
failure to deliver an original executed counterpart shall not affect the
validity, enforceability, and binding effect of this Amendment No. 7 as to such
party or any other party.

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        IN WITNESS WHEREOF, the parties hereto have caused this Amendment No. 7
to be duly executed and delivered by their authorized officers as of the day and
year first above written.

WACHOVIA BANK, NATIONAL
ASSOCIATION, successor by merger to Congress
Financial Corporation (Florida), as Agent and a
Lender

By: /s/ Martin J. Coloson, Jr. Title:   Vice President
            Wachovia Capital Finance

AGREED AND ACCEPTED:

TRAILER BRIDGE, INC.

By:  /s/ John D. McCown

Title:    Chairman and Chief Executive Officer