There is a program down in the BVI that has been going on for a long time that is called Action Quest. They take 10-15 51ft sailboats staff them with two experienced sailors and about 10 14-18 year old kids. They teach them sailing, diving, water skiing, windsurfing, etc.

I was lucky enough to go down twice when I was 14 and 16 to the program and traveled by myself down there each time. I got to go twice because we got special pricing since I was best friends with the son of the owner of the program.

Long story but even with all those teens we all had a blast, were responsible, and learned a ton. I say take the teens, teach them how to sail, and let them handle the boat as much as possible to give them hands on experience.

I plan to take my two step kids down there in two to three years when they get to be 16-17.