It's impossible to answer your question - if you include all the Bahamas Out-islannds there are over 1,000 islands and cays in the Caribbean/Bahamas and 10 times that many resorts/hotels - each is different with it's own unique attributes, history and culture and each has it's own set of "fans". You can ask 100 people which island is their favorite and you'll get 100 different answers. Somewhat like asking someone which type of candy they'd like!

Your best bet is to do some basic research and read general descriptions about the different islands (start with the major ones) and pick one or two that most appeal TO YOU. You can then do some in depth research about those islands.

You'll find some very good summaries by using the "Destinations" link at the top of this page. Click through to the "Caribbean" and read what's there. It will help you narrow your search.

The Caribbean side of Mexico. We've been going for the past 10 years. Though not techinacally an Island. Very rich in culture and history. Lots to do off the resort for exploring like Mayan ruins, eco parks, snorkeling, cenotes, caves, zip lines, etc. Good dining and entertainment opportunites on 5th Avenue in Playa del Carmen. Good AI resorts in various price ranges with amazing pools. Good beaches. We keep going back because we haven't seen/done everything there is to offer and we are very active on vacation. Also, it's one of the least expensive destinations out there.

welcome.topuertorico.org/history.shtml
Best Carib history/culture for me
www.elconvento.com wonderful historic hotel from personal exp.
Stellaris is nice resort there good deals betterbidding.com
$80 for more budget. Road trips are great there carrentals.com Caves El Yunque rain forest Ponce nice
lots of history also. spirit.com good cheap flights.

Happy Travels!

I haven't been to all of the islands but out of the ones I have been blessed to visit I would vote for Puerto Rico. Walk the cobbled streets in San Juan for history, and wonderful architecture!

Puerto Rico is a good choice. I haven't been to eastern Mexico, although I have been researching it and it also looks great. You should also consider Barbados, which has a lot to explore. My favorite island is Anguilla-it does have a heritage trail, remnants of a rain forest, several churches with beautiful architecture. Former Chief Minister Emile Gumbs used to conduct a tour. And you can do a day trip to St Martin/St Maarten, or to Saba(by ferry for the first, by plane for Saba)

I'd look at Grenada. Fascinating history, beautiful beaches, jungles to hike in. Interesting small city to explore. Easy to get around.

Please consider Barbados and Curacao - both have incredible beaches, clear waters,safe feeling and met friendly people. Vacationed in Curacao in 2010 and would revisit it in a NY minute - full of historial sites and informative museums. Were in Barbados last April and loved it - have fun and travel safely.