What do you want? I live in the British Virgin Islands and have been to a few of the other islands.
Barbados is ok but you'll be falling over Brits. Antigua is about the same, some nice resorts but avoid anything from a Virgin/Thompson brochure.
Dominica (not the Dominican Republic) is Beautiful, unspoilt, low impact tourism, and some of the best diving in the Caribbean, black sand tends to put people off but if you want a Hiking/Diving holiday it's fantastic.
St Vincent hasn't really got the tourism thing yet, but there's some nice resorts. The Grenadines are beautiful.
BVI is the sailing capital of the Caribbean, you can bare boat (sail yourself) or charter with a captain. There's some amazing beaches around the islands. Diving is excellent. Surf is good. There's also some very upmarket resorts. Peter Island, Little Dix, Biras Creek and Bitter End.
Puerto Rico has a nice combination of being a big island but with some good scenery, plenty to do, some good riding (MTB & Darkside) Old San Juan is very cosmopolitan and with everybody speaking Spanish it combines a feeling of mainland USA with Europe. There's also this in February http://www.vueltapr.com/Blog a great way to see the Island, meet the locals and do some great road riding.
St Kitts & Nevis are typical Caribbean Island.
St Maarten/St Martin (half dutch – half french) is ok, but very crowded and very busy when they get the cruise ships in.
Guadaluope and Martinique are part of France, not been to either of them.
Have a look at this forum http://www.traveltalkonline.com they have some very good advice for BVI, St Martin and the rest of the Caribbean.
I'd avoid a package holiday and try and go independently to get the best out of the Caribbean.