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Island itinerary help - 12/20 to 12/9 or so, 2 adults, 2 teens

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Hello, Fodors:

New to Caribbean travel and not big travelers in general, but we're looking for a pleasant, low-stress warm weather getaway over Christmas. We're not exactly the dedicated AI type but some compromise between AI predictability and genuine local color would be nice.

We want to travel shortly before Christmas and return around New Years, maybe just after. I know, I know.

Looking for:

Some beach time but need more than just that
Some snorkeling, maybe boat/air tours, or a small sailboat rental (I can sail)
Some non-beach natural beauty - not real hikers, but would like renting a jeep for touring
Some "old town" charm and quaint/historic urban areas, but don't need a metropolis
Prefer condo/villa/house rental to straight hotel - 2 bedrooms and living room
Some shopping, but don't need super-high-fashion elegance
General fun

Don't really need:

Hard core hiking or adrenaline sports

We're thinking of Puerto Rico or USVI but are really looking for suggestions. I'm starting passport renewal process Saturday so they should be available by departure date. Of course we want to make reservations soon since it is high season.

I've looked into a few multi-stop cruises that might fit the bill but they tend to depart/return a little early in order to split the holidays into two outings. We're not sold on the cruise idea but it is not out of the question. I just think the the idea of renting a villa/condo and a jeep would make for a more interesting trip.

Thanks, Fodors folks! I know there are a lot of you out there that can help us narrow the choices and hit the good spots.

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