Pamda beat me to it. For information on Windjammer, check windjammer.com
and for an active message board like this one but specializing in Windjammer
check coconutelegraph.com. It used to be an official windjammer sight , and was down from August until Jan or Feb of this year. It is now back up and becoming quite active again. Mrs. Bill and I are booked on the Flying Cloud leaving Tortola in the BVI on
May 26. We are staying on Tortola in a hotel on Cane Garden Bay from the 24th. By coincedence the BVI music festival is that weekend on the beach at Cane Garden Bay.
This might be the sort of thing you are looking for. They have 6 ships and have itineraries from 6 to 13 days in all parts of the Caribbean.
I would also agree with checking out CArnival, RCCL and Princess. Both my husband and I really loved our RCCL Explorer cruise, you may want to check out one of the Voyager class ships, lots to do! The cruise is as fun as you want to make it, so make it happen what ever cruise you go on, have FUN