If you want a weekend close to home, Asbury Park, NJ is another place you might enjoy at the Empress Inn. I believe the hotels nightclub is NJ's largest gay bar, right beside a beach and the pool is a lot of fun. People of all ages, so there would be plenty of guys around your age.

For flying I would recomend Lauderdale for someone your age domestically.

Internationally Barcelona could be a good trip. And enjoy the beach at Sitges.