Caribbean vacation, where to go?

I’d like to go on a vacation somewhere in the Caribbean. The only place I have gone on a tropical vacation was San Pedro, Belize and absolutely loved everything about the place. What I really loved was going into town and seeing the way of life there. The town was bright, packed and the main way of transportation was by golf cart. My goal on vacation is to experience things that make each place different and to see the actual character of each place I visit. I wouldnt really know if this is true as I’ve only been to one place but it seems like an all inclusive really limits that experience, maybe I’m wrong. I love the beach and anything having to do with warm ocean water, but I don’t want to be limited to sitting on a beach and things that I could do here in America like clubbing or going out to eat in fancy restaurants. These travel sites seem to focus on these sorts of things, but I’m looking to go somewhere that leaves an impression on me like Belize has. I am adventurous and would love to have the options to do things a bit more out of the box. Swimming with the marine life, trying local foods, meeting people and seeing the local art was something I enjoyed there. Where is somewhere in the Caribbean that you have been that stood out from other trips and why?


My favorite island is St. Martin.

Anguilla stood out for me (although that was many years ago now). We got a small place rented a car (even though the island is that big). Drove around and saw anything. Picked up local hitchhikers. Went to the "super market" which of course is smaller than a 7-11 here. Ate a great restaurants (Anguilla is known for restaurants) but also bought a lot of fresh fish and made our own meals (often lunch and then eat out for dinner). The funny thing is that Anguilla is a ferry ride from St. Martin, but feels like a world away.
Yes, you want to stay away from all inclusive or places that have a lot of all inclusive resorts as the "local area" is just a big tourist trap (Cozumel, most of Dominican Republic, etc) and not what you are looking for.

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