I’ve been to a bunch of places in Caribbean, and I’ll throw in my $0.02. I’ve been to:
Jamaica: Ocho Rios & Montego Bay
Puerto Rico: San Juan, Mayaguez & Rosy Roads
Bahamas: Bimini, Freeport, Nassau (and some uninhabited islands)
DomRep: Santo Domingo & Puerta Plata
Key West (Hey, it might as well be)
St. Thomas, USVI & St. Johns
Gitmo Cuba (special pass required, but actually not a bad place)
IMHO, if you just plan on staying in some all-inclusive resort, and never intend on leaving the facility, then I’d say it really doesn’t matter what country you go to. But if you plan on sampling the local culture, I’ll offer the following:
Jamaica is truly beautiful, with absolutely stunning scenery. However, it’s a violent place, and you’d really need to be on your guard at all times. Ocho Rios has Dunnes River Falls, which is quite a famous tourist trap, and lots of fun. Also, you can find some crazy deep lake, and the beach where "Cocktail was filmed. Eh, it’s a nice beach. (Complete with “Cruise Bar”) I think that was near Montego Bay. I’d never pay to go to Jamaica.
DomRep, while living up to its reputation as a corrupt and dirty 3rd world country in Puerta Plata, I actually found Santo Domingo quite pleasant. We had no problems from the locals, and the downtown area was very historic and clean. The water leaves a little to be desired, but otherwise nice. We spent about 3 days there. We had stowaways sneak aboard the ship one night, and hide in a berthing area to try to make the trip back with us to the states. Did I mention we were on a Coast Guard cutter? No kidding.
USVI, was awesome. It’s very “Americanized”, so you’d feel most at home there, but there’s no mistaking it’s a Caribbean island. Huge mountains makes for stunning scenery, and a great place to pick up jewelry. Seriously, they have more jewelry stores there than anywhere else in the world (literally? I dunno, seemed like it). It’s crazy. Pretty happening nightlife, as I recall.
Puerto Rico, was nice, but I couldn’t shake the feeling that I was still in the states. Old San Juan, while perhaps a somewhat dangerous place, was the area I liked the most. The street parties on the weekends look like a tourism commercial, and yet it really happens. Real historic place with lots of tourist spots.
The Bahamas have quite the setup in Nassau - Paradise Island. It’s like Vegas with water. Lots and lots of water. If you’re into resort type partying, then think about Paradise Island. Great people, great food, typical tropical paradise beaches and all the big time casino gambling you can handle. I love the Bahamians as well. I’ve been afforded the opportunity to work and go to school with several Bahamians, and I can’t speak highly enough of them.
And finally - Cable beach at Gitmo has some kick-ass beach parties!
I know quite a few people who’ve been to the islands further out to the East in the Caribbean chain, and they all seem to favor those islands when this type of conversation comes up.