SECURITIES PURCHASE AGREEMENT
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 ”).
WHEREAS, subject to the terms and conditions set forth in this Agreement and pursuant to Section 4(2)
of the Securities Act of 1933, as amended (the “ Securities Act ”) and Rule 506 promulgated thereunder, the
Company desires to issue and sell to the Purchaser, and the Purchaser desires to purchase from the Company
securities of the Company as more fully described in this Agreement.
NOW, THEREFORE, IN CONSIDERATION of the mutual covenants contained in this Agreement,
and for other good and valuable consideration the receipt and adequacy of which are hereby acknowledged, the
Company and the Purchaser agree as follows:
Definitions . In addition to the terms defined elsewhere in this Agreement: (a) capitalized terms
that are not otherwise defined herein have the meanings given to such terms in the Debenture (as defined herein),
and (b) the following terms have the meanings indicated in this Section 1.1:
“ Action ” shall have the meaning ascribed to such term in Section 3.1(j).
“ Adverse Effect ” shall have the meaning ascribed to such term in Section 4.15.
“ Affiliate ” means any Person that, directly or indirectly through one or more intermediaries,
controls or is controlled by or is under common control with a Person, as such terms are used in and
construed under Rule 144 under the Securities Act.
“ Applicable Percentage ” shall mean with respect to each Qualified Equity Offering, 50%, if the
Equity Valuation on the date of the Offering Notice for such Qualified Equity Offering is equal to or
greater than $10,000,000 but less than $15,000,000; 75%, if the Equity Valuation on the date of the
Offering Notice for such Qualifi