Yes, parts of Grand Cayman are touristy (7MB and George Town). If you don't like that, head east and you won't see a store, business or resort for miles along beautiful stretches of beaches, and it is very unpopulated. For a really remote experience, fly to one of the other islands. While GC is certainly not a cheap or even medium priced location, we love it and to us it's more than worth the extra expense. Safe, and absolutely no solicitations on the beaches or anywhere else. It all depends on what you are looking for and what you are willing/able to spend.

Hands down-Anguilla is my top Caribbean destination. Since discovering it four years ago, my husband and I have not brought ourselves to anywhere else...and this coming from a couple that has been all over the Caribbean. My second choice would be Grand Cayman-which was our favorite up until the time we found Anguilla. My third choice would be Playa Del Carmen Mexico. You can't go wrong with any of them. First two choices are expensive, but to us it's vacation and we splurge.

My top three (not in order):

Curacao
Sint Maaten/St Martin
Mexican Riveria Maya

So the original poster wants, among other things, culture. So Grand Cayman was suggested quite often, among other places. My question is: What does culture mean in this context?

Agree marigold, Probably not much local culture BUT GC is still a popular choice as it offers everything else you could possibly want in a caribbean vacation.
great beaches, a great variety of restaurants.
tons of resorts and condo's.
lots of shopping (if desired)
Clean, upscale, safe & relaxing
plenty of water activities.
best snorkeling, diving in caribbean.
best standard of living in the caribbean.
hard to argue with that!

I agree, that you really can't pigeonhole the "best" places to go, because it depends on what you're seeking. The Cayman Islands are GREAT for diving, but not scenery. The US Virgin Island are good for scenery, ease with the currency, etc. And so it goes. If you want a foreign flair, try Guadeloupe, a French possession, like Hawaii is to the U.S. But be prepared with the French, as they really do not speak English there (or didn't when I was there some years back). GREAT food, all imported from France, both in the restaurants and grocery stores. A real out of the way place - Tobago, with great steel drum music, and the largest brain coral in the world as part of the underwater scenery.

See?? Every place is indeed different. Any one place can give you great experiences and memories to last a lifetime.

St. John
Curacao
Grenadines, but not Young Island Resort

bookmarking

St. Maarten (food & nightlife), Montserrat (a live volcano & the best people) & Saba (hiking & eco)- & they are all right together so this IS doable.

My top faves:

St John:
Very laid back, lush, amazing beaches, great snorkeling, not crowded, quiet...but fun places for some nightlife, plenty of restaurants, very safe feel. It satisfies the majority of (OUR) needs.

Grand Cayman:
Very friendly, great beaches, great snorkeling & diving, excellent restaurants, very safe. Down sides are that it does have some conjestion, and some built up areas, but they are easily avoidable. It also isn't the prettiest island, as it's dry & scrubby. Was our fave until we found St John.

Been to many others, but none that I'd call a favorite.

As others have clearly stated, this is all based on opinion, and more imporatntly (personal taste). The most important thing you must do is make a list of the top 5 things YOU want from your vacation. From there, you can narrow down what island might best fit your needs.

ST.JOHN,,,ANGUILLA,, BVI"S !

1) Puerto Rico: Great history / U.S. only rain forest / Large island with many facets. Spanish/Latin culture with U.S. overtones
2) St. Martin/SintMarteen - 2 cultures on one island; Dutch and French. Great nightlife, good shopping, casinos.
3) Nevis: Small, lush, rain forested extinct volcano. Lots of hotel choices from the only 5 diamond resort in the Caribbean (Four Seasons) to small beach and/or mountain plantation hotels, eco-tour friendly, check on local happenings during your visit which range from local calypso (Kaiso) competitions to beauty pageants and horse races, bicycle races and beach road runs. Culture that hits close to home for U.S. and British students of history with Alexander Hamilton, Admiral Lord Nelson, Cottle Church which was the 1st church to allow whites and blacks to worship together and St. Thomas Church - the oldest Anglican Church in the Caribbean, AND the oldest synagogue building in the Caribbean.