Did the Navy "All Hands" swim with the RNZN back in the 80's during WestPacs, coastal deliveries and deliveries back from the UK and also close to NZ where the water is a lot cooler. It was always a great time. I've also jumped over the side in the middle of the Pacific while sailing our 38'...
^ Charleston. Can't go wrong. My wife's from Charleston, we lived there before moving to SoCal. Food, housing, water right there, and the golf courses within 90 minutes will more than make you happy.
I sailed a Sunfish from St Maarten to St Barts once. 1989, working on the now gone Sir Francis Drake, It was my day off, may or may not have told the skipper. They passed me on the way over, he may or may not have been pissed. Long time ago, was a lot of fun back then.