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Turning 40 in the Caribbean

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Hello! I am turning 40 and want to travel to the Caribbean with friends and family. I have been researching trying to determine where to go. I have been to Jamaica several times.. loved it. I stayed at Couples Swept Away in Negril (AI) food was excellent- best AI I have been to. I have been to the DR and Playa Del Carmen. I am interested in USVI, Puerto Rico, Bahamas, St Marteen and St Lucia. Let me list what I am looking for and hopefully this forum can guide me in the right direction. I'm looking for sun and fun! A day or so of sightseeing, but really want to kick back and enjoy life w/ my closest friends.
Bday is September 3rd - I am turning 40 but not ready to start knitting and watching Wheel of Fortune for entertainment :)
I would be traveling w/ couples and some singles
I want to be close to shopping, restaurants, and bars/clubs - I want to be able to split up and do our own thing when we want to
I'm trying to determine if we should all stay in a large house or all book the same hotel. In Negril I think the best option is a resort.. not sure about the places I listed above. I'm social- my bf, not so much. I think sharing a awesome house w/ pool would be great.. but it would need to be on the beach w/ a pool and not too far from some night life.

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