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Resort near a town?

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I'm just starting to look for a place for a 4 to 5 day stay, or maybe a week mid February of next year for our first anniversary. We aren't sure which island and it is all mind boggling, frankly.

We aren't really big resort people, and tend to HATE those all inclusive places where you eat on site with chef prepared food every night. We'd rather wander off into town and eat at some colorful local spot. And we'd love poking around during the days in a town of a little size that isn't just cruise ship buying spots. And we're not really into spas, etc. Big family places are a turn off. Having a car or jeep for exploring an island could be fun, and sounds better than arranging a shuttle with a resort to specific places or organized tours. We do want beach front for just general relaxing perhaps on a nice balcony as well as the beach itself.

We aren't looking to take out a mortgage to pay for this -- something like a couple hundred dollars a night would be wonderful -- $1000 a night is a no-go.

So I guess I"m asking. Does this sort of thing ring a bell with anyone? Most resorts seem to be in the middle of nowhere rather than adjacent to a town. We're not even opposed to a nice condo or hotel with a room facing the ocean -- essentially within a town of some size. Castries, St. Lucia or Bridgetown, Barbados come to mind. I've even thought of somewhere around San Juan, Puerto Rico, which would also offer the easiest and cheapest flights for us.

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