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Introductory Island for a West Coast Girl?

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What representative Caribbean island would you recommend to a 51 year young "girl?"

Vacation dates: mid to late October 2014, 7 to 8 nights
Budget: moderate to lower end of splurge (I may try to use mileage to get from Alaska to Florida and then fly out of Miami in order to spend more on the lodging)
Number of travelers: Me, myself and I. So I'd like to feel safe and not be overly cautious about being out and about sightseeing.

I'd like to spend a couple of days on the beach or next to a pretty pool to get my fill of vitamin D. After that, I can't sit still, so I'm looking for easy walks/hikes, maybe a little shopping or 1 or 2 excursions, and good food and wine!

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