Exhibit 10.9

September ____, 2008

Gulfstream International Group, Inc.

3201 Griffin Road, 4th Floor,

Ft. Lauderdale, Florida 33312

Re:  Conversion of Debenture

Gentlemen:

Reference is made to a $1,000,000 Junior Subordinated Debenture of even date
herewith (the “Debenture”) issued by Gulfstream International Group, Inc. (the
“Company”) to Gulfstream Funding, LLC (the “Investor”).  Capitalized terms used
herein that are defined in the Debenture shall have the same meanings herein as
therein.

1.

Conversion of Debenture.  Notwithstanding anything to the contrary set forth in
the Debenture, the Warrant or the Subscription Agreement, the Investor and its
successors and assigns shall have the right to convert all or a portion of the
principal amount outstanding under the Debenture into shares of the Company’s
Common Stock, par value $0.01 per share (the “Common Stock”), at a price of
$3.00 per share in accordance with the terms and conditions hereof.

A condition to the exercise of such conversion right shall be the termination of
rights to acquire 58,333 shares of Common Stock pursuant to the Warrant.

2.

Exercise of Conversion Right.  In order to exercise such conversion right, the
Investor (or any such successor or assign) shall deliver written notice of the
exercise to the Company accompanied by the Debenture and the Warrant.  Such
notice shall specify the portion of the principal and/or interest under the
Debenture to be converted.  Promptly following receipt of such notice, the
Debenture and the Warrant, the Company shall deliver to the person indicated in
such notice:

a.

a certificate in the name or names of the persons indicated in such notice for
that number of shares of Common Stock equal to the quotient of the aggregate
amount of principal and/or interest of the Debenture to be so converted divided
by $3.00;

b.

if less than all of the principal amount of the Debenture shall have been
converted, a new Debenture in a principal amount equal to the unconverted
portion of the principal of the Debenture on which shall be noted the then
accrued and unpaid interest under the Debenture after giving effect to the
conversion of any interest under the Debenture; and

c.

a new Warrant to acquire that number of shares of Common Stock equal to the
number of shares of Common Stock issuable upon exercise in full of the Warrant
prior to the exercise of such conversion right less 58,333 shares.

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Please indicate your consent and agreement to the foregoing by executing a
counterpart of this letter agreement and delivering it to the undersigned.

Respectfully,

GULFSTREAM FUNDING, LLC

By

Name:

Title:

Consented and agreed to as of the date

above written.

GULFSTREAM INTERNATIONAL GROUP, INC.

By

Name:

Title:

The undersigned agrees that the exercise of the conversion right with respect to
the Debenture described in the foregoing letter agreement shall not be limited
or restricted pursuant to that certain Subordination Agreement dated September
____, 2008 among the Company, the Investor and the undersigned.

SHELTER ISLAND OPPORTUNITY FUND LLC

By

Name:

Title: