Gayest Caribbean islandsMy partner and I would like to know what island is gay friendly and has the most to offer by way of gay beaches, clubs, and bars.If you're looking for gay-friendly Caribbean islands, you've got some great destinations to choose from. My top vote for beaches and bars goes to Puerto Rico. San Juan is one of the gayest spots in the Caribbean. Many gay clubs have moved to the new arts and culture district of Santurce, but don't miss Krash Klub, still in the Condado and still the main gay club in town. Condado Beach is a bustling stretch of sand, a short cab ride from Old San Juan.Alternatively, you won't find much in the way of nightlife in St. Maarten, but sun worshipers flock to Cupecoy Beach on the Dutch side of one of the Caribbean's favorite gay retreats. Cupecoy is the gay beach, usually jammed with nude, toned bodies. It's made up of three white beaches nestled beneath caves, rock formations, and cliffs; clothing is optional toward the northwest end of the beach. Finally, on quiet St. Croix, the pristine beach just south of the town of Frederiksted lies within walking distance of the gay-oriented Sand Castle on the Beach resort. The resort is the epicenter of the island's LGBT nightlife and is a lively place to vacation.