Are you familiar with any of the Caribbean islands and/or have a favorite island? For Mexico, the premier nude resort is probably Hidden Beach. Haven't been there myself, but my understanding is that there isn't really a beach at the resort (despite the name of the resort) . There is another thread here about Hidden Beach. There's not a lot of nude resorts left in the Caribbean, unfortunately, but if I were going to pick one now, it would probably be Grand Lido Negril. It is a small section of a much larger resort. My understanding is that it is now mandatory nude on the beach, which I don't know if that would be helpful to a first timer or not. Maybe so. The rest of the much larger resort is all clothing required. I enjoy Negril in general, and you can venture outside the resort if you wish and that is interesting to me.