There are several options one have when choosing Caribbean for his sailing destination.  You may sail Bahamas choosing a Bahamas bareboat (catamaran or sailboat), hire a boat in Belize, charter a yacht in Antigua or enjoy a Tortola bareboat.  The most popular are Bahamas boat rentals.
Except bareboating, other popular destinations offer excitement.  The diving funs can enjoy diving in Dominica, scuba in Barbados or just a Cayman snorkel and the fishing enthusiasts can be in paradise fishing in Barbados, Bahamas, St Maarten or Grand Cayman.