I'm not a seasoned sailor like many here, but I've been on group charters in the BVI's, and I say there is no way you'll get anything near the pleasure of a charter if you do a land based vacation. The whole point is to have an all inclusive vacation where you don't have to handle money, worry about where to eat, or go through the hassle of arranging excursions. The first time we sailed, we didn't know our group very well, and it was not a problem at all. People are generally on their best behavior while on vacation, and they are taking the same risk as you. Go ahead, take the plunge....book on with the strangers, and I'll bet you'll have the time of your life!