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Living in the Caribbean part-time

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I'd like to visit St. John, St. Marteen, St Croix, Antigua, Anguilla, Barbuda and a few more islands to see what's out there. I would live in the Caribbean half the time and Florida the other half. I'm about 2 or 3 years away from making the move, but want to get a head start so I know where I want to settle when the time comes. I wanted to get a feel from a few people that have already done what I'm about to do. I'm looking for a safe island with great views of other islands in the area that would also be close enough to visit by boat and not have to take a plane to get there. I'm also wondering if there are some other lesser known little islands out there. The night life isn't that important, but going to see a show at a casino and maybe some live music every now and then would be nice. Anyone out there been through what I'm about to explore? Thanks for any input.

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