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Next Caribbean Destination?

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Hi all. I've now been to the Caribbean Islands 4x: Punta Cana & La Romana in the DR, San Juan, and most recently, Aruba. I enjoyed my time at all four locations, but the most in Aruba and San Juan as there were things to do outside of the resort and it was fairly easy to get around in a rental and public transportation.

Where else can I go where I can have the same thing? I am open to AI but i'd prefer the ability to choose from a variety of restaurants in town even if i have to walk or take a shuttle or something. i'm not a foodie so restaurants similar to regular american chain restaurants would do. Budget-wise, i'd like to stay < $2,000 for two including air & hotel flying out of DC.

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