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Baby-friendly destination in August?

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Our baby girl will be 5 months old in August, and we would like to take her on an island vacation before I return back to work. We do realize that August might not be the best month for Caribbean travel in terms of the hurricanes/heat/humidity but still want to give it a try. Does anyone have any suggestions on choosing a destination? We live in NY and looking for a vacation spot within 4-5 flight, since it will be baby's first time flying. Oh, and any tips on traveling with an infant are greatly appreciated!

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