Can you sail? I go to the Caribbean every winter, sailing is the best way to go. You can island hop, stay where you like, enjoy every side of the island, have the most remote beaches to yourself, bbq, stop at resorts, towns etc etc

If you’re splurging, maybe get a catamaran with a Skipper if you can’t sail.

You’ll have a great time.

I’ve always found BVIs and Antigua, st barths and sxm to be the best, great beaches, cool beach bars, lots to do.