Jamaica / Bahamas / Florida area

My husband and I are looking to spend a 2 or even 3 week vacation in the area this summer. Does anyone have good recommendations?

A friend recommended Anguilla but I’m not sure if it’s really relaxed. We don’t want it to be too touristy or resort style but I would really like the company of black locals or black American tourists.
 
Lucky to live in SW Florida. Lots of empty coastal islands with empty beaches. Best time is during the week when most people work. Take our boat, anchor off of beach, and get pounded by BBC naked on the beach. Sometime small fishing boats go by and they get a show....so hot!
way to go :)
 
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