0001354488-08-001916 Sample Contracts

COMMON STOCK PURCHASE WARRANT To Purchase 578,870 Shares of Common Stock of
Gulfstream International Group Inc • November 14th, 2008 • Air transportation, scheduled

THIS COMMON STOCK PURCHASE WARRANT (the “Warrant”) certifies that, for value received, Shelter Island Opportunity Fund, LLC or its registered assigns (the “Holder”), is entitled, upon the terms and subject to the conditions hereinafter set forth, at any time on or after the date hereof (the “Initial Exercise Date”) and on or prior to the close of business on the sixth anniversary of the Initial Exercise Date (the “Termination Date”) to purchase up to 578,870 shares (representing an amount equal to 15% of the Common Stock at the date hereof calculated on a fully-diluted as-if converted basis) (such greater amount being the “Warrant Shares”) of Common Stock, par value $0.01 per share (the “Common Stock”), of Gulfstream International Group, Inc., a Delaware corporation (the “Company”). The purchase price of one share of Common Stock under this Warrant shall be equal to the Exercise Price, as defined in Section 2(b).

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SECURITIES PURCHASE AGREEMENT
Securities Purchase Agreement • November 14th, 2008 • Gulfstream International Group Inc • Air transportation, scheduled • New York

THIS SECURITIES PURCHASE AGREEMENT (this “Agreement”) is entered into as of the 16th day of September, 2008, by and among GULSTREAM INTERNATIONAL GROUP, INC., a Delaware corporation (the “Company”), and GULFSTREAM FUNDING, LLC, a Delaware limited liability company (the “Investor”).

SECURITY AGREEMENT
Security Agreement • November 14th, 2008 • Gulfstream International Group Inc • Air transportation, scheduled • New York
GULFSTREAM INTERNATIONAL GROUP, INC. PUT OPTION AGREEMENT
Option Agreement • November 14th, 2008 • Gulfstream International Group Inc • Air transportation, scheduled

Gulfstream International Group, Inc., a corporation organized under the laws of the State of Delaware (“Company”), hereby agrees that, for value received, Shelter Island Opportunity Fund, LLC, its successors or assigns (the “Holder”), is entitled, subject to the terms set forth below, to require the Company (as defined herein) from and after the earlier of (i) the repayment in full of all amounts owed to the Holder under the Company’s $5,100,000 Secured Original Issue Discount Debenture issued to the initial Holder on the date hereof (the “Debenture”) or (ii) the date that is 36 months after the Closing Date (as such term is defined in the Securities Purchase Agreement dated as of even date herewith between the Company and the Holder) (the “Put Commencement Date”), until August 31, 2014 (the “Put Termination Date”), to repurchase from Holder at the Exercise Price (as defined herein) up to the maximum number of shares (the “Put Shares”) of Common Stock (as defined herein) that are issua

SECURITIES PURCHASE AGREEMENT
Securities Purchase Agreement • November 14th, 2008 • Gulfstream International Group Inc • Air transportation, scheduled • New York

This Securities Purchase Agreement (this “Agreement”) is dated as of August 31, 2008 by and between Gulfstream International Group, Inc., a Delaware corporation (the “Company”), and Shelter Island Opportunity Fund, LLC, or any Affiliate thereof designated by it (the “Purchaser”).

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