You should check out Hedonism 2 in Jamaica. (hedonism.com) There are people from all over of all ages, shapes and sizes, and walks of life. A bunch of great, friendly, open, non-judgmental folks who want to have fun. There is no pressure to do anything you don't want to do. No means no. But also opportunities to explore whatever you happen to be into. Lots of good food, entertainment, water sports, activities, etc. Hang out with your swimming suit and your Kindle on the prude side, or get naked and join the party. You can find the groups going on the website. Some are more nudist, some more lifestyle, some diverse. Find a group that interests you and book. Nearly impossible to have a bad time there. Good luck!