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What island to stay at?

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My husband and I are planning a 5 year anniversary trip to the Caribbean. We're having trouble deciding where to stay. We're using Marriott rewards points for the hotel, so we're somewhat limited by their properties, which are located at Grand Cayman, Curacao, San Juan, St. Kitt's, Key Largo/Key West, St. Croix, and St. Thomas. Aruba is also an option, but not one H is crazy about. If anyone has stayed at a Marriott at these places, would love to hear your feedback.

Our main goal is a relaxing, romantic vacation with lots of time on a beautiful beach but we'd also like enough attractions/to do's to break up the beach days. H is a history buff and we're not into the party/nightlife scene. Good food is important. We prefer a lush, tropical environment, but I'm not entirely sure this is realistic; I believe the area is more arid. We're planning on staying 8 - 9 days.

1. What's your budget? We're really flexible here since the room is being paid for with reward points.
2. What are your travel tastes? (tent, modest, luxury?) Luxury
3. Want history or basically scenery? Both
4. Want to walk around or drive? Prefer to walk take cabs, but would drive to the right locations/attractions
5. Want big island or small? Prefer small, but would also like a few days' worth of things to do and good food
6. Hilly or long flat beaches? Flat
7. Turquoise water, or black sand beaches? Turquoise water
8. Scuba and snorkel? Yes, please! (Neither of us are scuba-certified, though. Should we do this before we go?)
9. Upscale or do you mind vendors approaching you? Upscale (ok with being approached in the right environment, like a bazaar-type setting)
10. Scenery or water sports? Prefer scenery but would be open to sea-kayaking or the like. Not seeking out jet-skiiing, parasailing, etc.
11. Secluded or crowded? Secluded for sure
12. shopping? Nightlife? Casinos? Would like some local bazaar-type shopping, but am not interested in American malls or the like. Nightlife - meh, not really. Casinos - perhaps if it were there, but not a must-have by any means.
13. Topless/nudity? Topless ok, but I wouldn't seek it out
14. Easy access from States or off the beaten path? Either
15. Sailing? Yes
16. Island hopping? Am open to this. Any suggestions?

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