Charter Sail boat recs for the Caribbean?

Where? It's a big sea.

If the BVI, the THe Moorings out of Tortola.

Moorings/Tortola/BVI is a great choice, especially if it’s the first sailing vacation for any of the couples. It’s easy sailing, usually between islands, in protected waters. We always bareboated (sailed the boat ourselves). They do have skippers and cooks. If you go that route, I’d recommend skipper-only, since you’ll want to eat suppers ashore to see the islands. From what I’ve heard, the hired-skipper experience can range from good to bad. The bad experiences seemed to always be with native skippers, who were less accommodating in their duties.