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I have had the good fortune to visit many Caribbean islands and can offer this advice.
If your main focus is beach and relaxation, I suggest Anguilla or Jost Van Dyke (British Virgins). They are small, friendly, quiet, uncrowded, and very relaxing. They are not the place for a single guy looking for (powered) water sports, casinos, and night clubs. Give 'em a Google!
For a more festive environment, but still including nice beaches, try St. John (USVI).
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