Some suggestions:
1. Hedonism II in Jamaica. My best vacation ever. I went to the nude beach and saw this young guy from New York who was having one of the female hotel staff (an attractive young Cuban girl) paint the head of an Inca God on his erect cock. I will never in all my life forget this priceless moment. The beach is not the greatest, but the drinks (which are all included) are. Had numerous drinks I never heard of before. Great place to go for the money if you are a lush.
2. Club Med in Turks & Caicos. Great beach. Not much on the island, though, if you are into sightseeing. Weather is great. In 2 long vacations there, only rained one day. Very dry climate and superb beach. Lots of activities and water sports but beware they have a serious shark problem which no travel agent will tell you about. The government dumps trash in a remote area of the Island to attract the sharks away from the tourist areas. There have been fatal shark attacks in recent years, and the natives admitted to me when I pressed them that there is a problem.
3. St. Martin, French side of Island. Best food in the Caribbean, and best nude beach (Orient Beach). Mountainous island, great restaurants, Dutch and French cultures on the 2 different sides of the island. Casinos and gambling but no nudity on the Dutch side; great restuarants and nude beaches on the French side. Beach is okay, somewhat rocky. Climate windy and unpredictable with the trade winds blowing in at all times.
4. South Beach, Miami. Was here recently. Superb beach. Expensive as all hell but fun place to go if you are in the 25-40 age bracket and looking for fun. Check out Mangos, the best bar on the strip on Ocean Ave. This is the place where the waitresses dress in bikinis and dance on the bar.
5. Cancun. Not the greatest beaches and the food can be scary for the bowels, but lots of great places to go like the ruins at Tulum and Chichen Itza, and Isla de Mujeres (Island of the Women). If you are a single woman you should not travel alone in Mexico as there have been numerous problems with kidnappings and shakedowns. If you go to any of the tourist sites go with a group on a bus.
Being American I cannot easily travel to Cuba, so no report on that Island at this time.