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Which island to visit in late September/early October?

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Hi everyone..hope everybody is enjoying their summers so far. I need some advice and suggestions as to which Caribbean island/s would be your top choice to visit for a total-relax, beach vacation with family (me-hubby-our 5-yo) during the last week of September or first week of October considering the weather as well as flight ease (non-stop) from philly/Newark? Do you see any chances of finding the dream vacation destination with turquoise waters, white sandy tranquil beaches, and 5-star service resort at that period? Many thanks in advance for the help!

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