Just remember that if you go with the Caribbean, you have to keep your fingers crossed because it will be smack dab in the middle of hurricane season. On the flip side, if you luck out on the weather, you end up scoring on the crazy deals that you can find for the islands that time of year.
Jamaica - I've been to Grand Lido Negril twice and Couples once. They are right next door to each other, beautiful beach. Both are all inclusives, no kids. Food, booze, and service at Couples was fine, but Grand Lido was over the top. If you can get a good deal, go with GL. Some people have safety concerns with Jamaica, but if you're staying at a beautiful resort, and it's an all inclusive, then there's no reason to leave to resort to go to some bar or out of control market. The beaches at the resorts in Jamaica are private, so you don't have to deal with people harassing you all day trying to sell you trinkets, or braid your hair, all the while the 6 year old that's with them is cleaning out your wallet that you "hid" in your shoe. The only person selling stuff is the guy that runs his skiff along the beach all day. There's a net about 75 yards off the beach, and he runs his skiff along the buoys all day. Swim up to him, and he'll sell you some, um, er, stuff.
St. Lucia - Been to Sandals, beautiful island, beautiful resort, great service (not as good as service at resorts in Jamaica). Only downside is that the beach isn't private, so you deal with people walking up trying to sell you crap all day. Much safer feeling in St. Lucia than Jamaica, but it ends up taking a while to get there. Usually have to go thru Puerto Rico, then take a twin prop for 3 or 4 hours.
St. John - LOVE St. John. Been 4 times. Beautiful island, always feel safe. Always rented villas there. They can be a lot less expensive than you think, especially offseason. That being said, you have to rent a car, and you'll need to buy food/booze. Large markets on the island to buy stuff, but we've also brought food/booze down. There are some great restaurants on the island, and typically we eat at the restaurants half the nights, dinner at the villa the other half. Cooking on vacation sounds strange, but, grilling/eating filets on the villa's porch as you watch the sun set behind St. Thomas is pretty friggin' sweet. If you go this route, let me know and I can suggest some websites, villa rental agents, and some specific villas.
Mexico - post-college, I've only been to the Riu Palace in Playa del Carmen. Insanely beautiful all-inclusive resort, huge, beautiful beach, fantastic food, but my wife and I both got sick.
Personally, I wouldn't do the Carribean that time of year. I'd book a week in Napa/Sonoma instead (wine, spas, fantastic food, can't go wrong)
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You better be serving Lobster & Filet.
