Favorite Caribbean Island?

Bonaire. Diving and beaches, not jam-packed.

Thanks Ed - I've heard about Bonaire and it's spectacular diving. Any hotels there that you prefer?

No knowledge. I used to have a pretty nice sailboat.

Nothing to add, but have fun!

Anita. My first choice would be Grand Cayman. Easy, clean, safe, and - a big factor for us - easy to get to from Midwest US. Providenciales Island in the Turks & Caicos also good choice. Don't care for St Thomas, Jamaica or Aruba.

St. Barts! It's a piece of French paradise in our own backyard. It has a reputation for being expensive and exclusive, but as long as you don't go in December or January, it's comparable to Anguilla and French St. Martin, but prettier and with the best restaurants outside of France. The development is very low key meaning no chains (other than Chanel, LV, etc), large hotels, casinos, or condo buildings but plenty to do. You can leave your stuff on the beach and snorkel all day and not worry about any one messing with it. We never lock the doors to cars or houses. Most don't even have doors. Think rose wine and house music at harbor cafes instead of boat drinks and steel drum bands. Even with all this, it's a relaxed and very casual place. Nice shorts at dinner and beach cover ups at lunch is the uniform. Shoes optional almost everywhere else. Let me know if you need any more info and I can load you up. My husband and I go once or twice a year and are headed there again this summer with our new baby. Enjoy your trip!

Virgin Gorda (Little Dix Bay resort). Take a day trip to 'the Baths' and also 'the caves.' Virgin Gorda is part of the BVI, and we can just always tell a difference with BVI islands.

Or, split your time between Little Dix and its sister resort, Caneel Bay on St. John. A day sail to Foxy's on Jost Van Dyke (which was written up as on of THE top places to have spent the Millenium in 2000) and a fun place to party (even during the day). Those who have been to Foxy's 'get it.' Great place to have lunch and drinks, right off a day sail. Usually the same day sailing will stop at White Bay (and visit at the Soggy Dollar saloon, in your bathing suit, for their signature drink).

Both Virgin Gorda and St. John are quiet, excellent food, and surrounded by wonderful natural beauty. But, neither Caneel or Little Dix is what I would consider a 'party place.' So, if nightlife is important, stick with St. Thomas. But, it is an easy ferry ride to St. Thomas from St. Johns......so you could stay at Caneel and ferry over to St. Thomas for variety/shopping, etc. If you go to St. John have a local taxi take you on an island tour, up to the tops of the hills, etc......you'll be glad a local is driving :)

Thanks so much everyone! These all sound amazing and I can't wait to get researching....hopefully the three of us can agree with so many great choices!

Another vote for St. John. What I most enjoyed was that much of the island is US national parklands. I really enjoyed the casual and undeveloped feel of that. You can certainly stay at the resorts. However, I stayed at Cinnamon Bay, which is part of the national park system. We were within 100 feet of the beach, with great snorkeling. And since it's part of a national park, it was also really affordable. They have a range of accommodations from camp sites, to tent cabins, to cabins with solid walls.

Another vote for Virgin Gorda! We used a sailboat that we chartered through The Moorings. The striking difference between the British Virgins and the U.S. Virgin Islands are (shamefully) the very little crime in the BVI as opposed the USVI! The Moorings, which we've used a number of times gave pretty intense warnings about leaving the boat to go ashore, and recommended leaving a person with the boat to avoid theft. Ugh. Little Dix Bay is very nice, and as the previous poster mentioned, the Baths are awesome.

There are also other boat rental places in Virgin Gorda if you are boat people. I'm sure you can get recommendations via Google or Trip Advisor. We've done a half dozen trips there, and have enjoyed every one of them. By boat you can get to some pretty incredible places, including the famous "Foxy's!" where they have a big beachfront barbeque every night.

Anita,

Any virgin island would be great, except for St. Criox because it's farther from the other islands. All the other islands, British and American are clustered together more to where you can take boating excursions to them. The snorkeling at St. John's is great. St. Thomas is the most developed in terms of hotels.
Negril, Jamacia is my favorite but there is not a lot to do but be lazy and enjoy one of the greatest beaches ever. Best sunsets I've ever seen. All Jamacian resorts are all inclusive and don't allow tipping.
Would never return to the Atlantis Bahamas again. Very expensive and crowded. Never felt more nickel and dimed my entire life.

Have fun

Easy answer – Puerto Rico. I’m not going to list all of the many reasons it’s the best island in the Caribbean, but do a Google search or reference Lonely Planet and see what you think. It meets all of your stated must-haves, plus you’ll get a 500 year-old Spanish city and military fortifications (Old San Juan), the only tropical rainforest under U.S. jurisdiction, and some of the best coffee on Earth. Food? Amazing! Beaches? Some are among the world’s top 10. Nightlife? Crazy!