We took a Windjammer Barefoot Cruise to St. Lucia last year. It was one of the best vacations I've ever been on. You said at night, visit a different island during the day. Capacity is only 120 people so you get to interact and know the people you are sailing with. I was quite skeptical at first but it was one of the best decisions I've ever made. Would recommend it for everyone and would do it again in a heartbeat.