Exhibit 10.8.6

                              CUSIP No. 892782 AB 9




$16,918,000                                                            No. 1


                       UNITED STATES GOVERNMENT GUARANTEED
                       SHIP FINANCING BOND, 1997 SERIES II

                   6.52% Sinking Fund Bond Due March 30, 2023


                                    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 SIXTEEN MILLION NINE
HUNDRED EIGHTEEN THOUSAND AND NO/100 DOLLARS ($16,918,000) on March 30, 2023,
and to pay interest semiannually on March 30 and September 30 of each year,
commencing March 30, 1998, on the unpaid principal amount of this Bond at the
rate of 6.52% 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.




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         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 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 $16,918,000
aggregate principal amount of sinking fund bonds, designated as its "United
States Government Guaranteed Ship Financing Bonds, 1997 Series II", all issued
under a Trust Indenture dated as of December 4, 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
December 4, 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 December 4, 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."


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<PAGE>

         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 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>


         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 September 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.


                                       4
<PAGE>


         "Reference Rate" applicable in respect of any Bond shall mean a per
         annum rate equal to 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
September 30, 1998, and on each March 30 and September 30 thereafter to and
including March 30, 2023, at 100% of the principal amount thereof plus interest
accrued thereon to such date, of a principal amount of such Bonds equal to
$338,360 and on March 30, 2023, 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.


                                       5
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         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 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.


                                       6
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         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 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.


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         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 December 4, 1997                TRAILER BRIDGE, INC.

(SEAL)

                                            BY: John D. McCown
                                                Chairman
Attest:

William G. Gotimer, Jr.


                                       8
<PAGE>


                    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 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 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: /s/ John E. Graykowski
                                                ----------------------
                                                John E. Graykowski
                                                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: /s/ Gerald R. Wheeler
                                                ---------------------
                                                Authorized Officer


                                       9
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                        PAYMENTS ON ACCOUNT OF PRINCIPAL


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