If you are planning your first trip to the Caribbean and you want to decide where to go to then this post is right for you.
If you are looking for something very touristy, international, and easy to access then pick between English-speaking Belize and the Spanish-speaking Dominican Republic. Both of them have all the comforts of the mainland US. And are good for both singles and couples. Both are relatively cheaper than other islands I list below. While Belize is not technically an island, it has great access to the Caribbean sea.
If you want to stay domestic then go to Spanish-speaking Puerto Rico. And if you want to go easy but international then choose Spanish-speaking Cancún. Both are good for partying, Cancún much more than Puerto Rico.
If you are looking for good snorkeling then go for English-speaking Cayman Islands. It is darn expensive though.
If you are looking for something off-beat and difficult to reach, go for Dominica. It is the most gorgeous lush green island in the Caribbean.
Aruba has European grace, European prices, and beautiful sandy beaches. The inner island is mostly a desert though. It is mostly for couples, don’t come here looking for nightclubs.
Jamaica has both party life as well as a natural beauty but is a bit high on crime.