Yes, I've always wanted to go on a gay cruise. However I have no gay friends so it's unlikely anytime soon. It would be weird with straight friends and I don't feel like going by myself, lol.
I've never been on a cruise but I've seen plenty of ads for all sorts of gay activities, including cruises. I would guess you don't really have to know anyone to enjoy a gay cruise, the ship will be full of like minded folks. After a couple days you'll know plenty of them. There are also plenty of gay friendly resorts and hotels, especially in the Florida Keys. Just google, you'll find plenty of information. I've been a nudist most of my adult life and have visited several resorts all over the country. Most are family type places but there is plenty of hetero swingers there too. Many of the women are bi, not so much with the guys. Not openly anyway. Hang around long enough and many of those places come alive after dark. There are also a fair number of nudist resorts that are gay friendly. I went to one in Missouri last summer and met a lot of nice friendly guys. Very relaxed atmosphere. Really enjoyed myself and look forward to going back. One thing I like about nudist resorts is there are folks of all ages there and not everyone looks like a model strutting around with their "tool" banging in to their knees. You'll be fine. Google "gay campgrounds', you'll learn a lot about both clothed and nudist places.