I've been on cruise ship destinations in the Carrib. I did stop in Dominican Rep. once, and it seemed fine where we were. Very poor population, though.
Bahamas are close and easy to get to. Like sailing among the Virgin (US and UK) Islands. Probably liked that best. Caymens has a sting ray petting area, if you like that. Aruba seemed interesting with its Dutch colonial heritage.
I think I'd like Cuba. First, what do you like to do? Sit on beach? Night life? Just chill?