bermuda pictures by l0wcash - Photobucket
I was in Bermuda last December. Very nice place and GREAT seafood. It was a quiet when I was there, even the locals said it was quiet than usual.
Bahamas:
nassau pictures by l0wcash - Photobucket
I was in Bahamas this past May. The rest of Bahamas is nice once you get away from Nassau. A few years ago the girlfriend and I were going to do a vacation at Tiamo on South Andros Island, but we never got around to booking rooms and ended up going to Costa Rica instead.
Costa Rica:
San Jose, Costa Rica - Apr. 07 pictures from costa rica photos on webshots
By far the best vacation I've been on. Granted this isn't the Carribean and we were on the Pacific side; the place is freaking awesome. They do have a cruise that docs in Limon (Eastcoast Costa Rica). The girlfriend went to Limon a couple years ago and said it was pretty nice. Not as lively as the Pacific side, but very relaxing.
Dominican Republic:
I haven't been to Santo Domingo since 2001 and I enjoyed myself. There are some nice hotels right on the water and some cool city tours. I went to Punta Cana in 2007. When I was there they were putting up condos pretty quick. There is a handful of all-inclusive hotels that cater to tourist.
I've heard good things about Aruba, St. Nevis and the rest of the small island. Can't really go wrong with any of them. Even Jamaica isn't bad, as long as you stay on the westcoast (Montego Bay, Negril or Ocho Rios in the north central).