We went on our first Disney Cruise this past April on the Dream. Had I known what I know now I would have stayed on the ship for our St. Thomas stop. It was just a lesser version of what we experienced the day before in Tortola. I’m starting to think there’s no good reason to get off on many of the Caribbean stops. At least not just to end up at a crowded beach eating bar food. I’ve been to St Thomas, Tortola, St John, Turks and Caicos (the capital not Providenciales- found that out the hard way when our ship docked), Belize, The Bahamas and a few other islands. If I were on a cruise, I wouldn’t Feel the need to get off the ship to go to any of them again. There isn't anything culturally that stands out or is all that interesting. The food isn’t that great. It’s not worth the hassle.
Not to say there wasn’t some beautiful beaches. Trunk Bay on St. John was stunning. But I didn’t enjoy any of the stops as much as I enjoy Cancun for example. The only places I’d probably get off the ship for at this point would be Puerto Rico, Jamaica, (Cuba if that ever happens) and Cozumel and I imagine they may be one and done’s too. At least as a 6-8 hour cruise stop. I’ll be targeting cruises with multiple Castaway Cay/ Lighthouse Point stops in the future. Just makes so much more sense with young kids. Not many of those islands are worth the hassle.