There are many options----
The Ritz Carlton on St Thomas has a few small boats, IC24
island sol sailing, windsurfing and kiteboarding school - Island sol
Cinnamon Bay on St John has a variety of small boats to rent
Water sports activities
Rob Swain in Nanny Cay Marina, Tortola has IC24s
BVI Sailing Lessons, Bareboat Catamaran Charters - British Virgin Islands (BVI)
Of course if you have plenty of $$$$'s you can sail a variety of boats at the Bitter End Yacht Club on Virgin Gorda
Caribbean Sailing Resort - Bitter End Yacht Club - 1(800)872-2392