When my daughter was 15, we allowed her to participate in a program offered by Broadreach
, the "Arc of the Carribean". She and 9 other teens sailed from St. Martin to Trinidad aboard a Beneteau 52 with two adult crew, a captain and 1st Mate, over a period of 4-1/2 weeks. The kids managed the boat, did their own cooking (kind of), learned and laid their own courses, stood watches--day and night--dealt with squalls and storms and did what any crew making the passage in mid-summer would do. They also spent lots of time ashore, climbing Volcano's, taking part in community service programs, working at marine resource centers (she liked working with a sea turtle rescue center best) and delving into the life on the various islands. The kids came from all over the world, Israel, Turkey, Italy, France, Norway, the UK etc. It was a great program and she had a great time and learned a lot. Upon her return, on the first weekend we went sailing, she confidently announced that I could relax as she and mommy could/would handle the boat (at 42 feet it was "small" by comparison to what she'd been aboard).
While we had some apprehensions about the trip, we equipped her with a SPOT so she could let us know where she/they were from time to time and we had friends in the islands discreetly "spy" on the boat/crew at various locations and send us reports. All-in-all, it went very well without mishaps other than the run-of-the-mill stuff that kids are prone to wherever they may be. Health insurance and medical evacuation insurance covered that eventuality if necessary (tho' it proved unnecessary).
More recently, my daughter and one of her best friends accompanied her aunt and uncle and another couple and their child, all from the Chicago area, to the BVI on a two week charter of a 47' Beneteau from Pro Valor Yachts
. While her aunt and uncle sail an O'Day 27 on Lake Michigan during the summer, they had never before sailed a larger yacht, nor anchored, and they admit that absent my daughter's knowledge/experience with a "big boat", and anchoring in particular, their trip would have been a lot more adventurous than they would have liked. An important aspect of that trip was again, travel insurance, and having the forms necessary to allow the adults to make medical decisions/directives for the "kids" (tho' my daughter is now 20) and HIPPA forms to allow hospital officials to disclose medical information to parents, insurer's and the like (American citizens are invariably transferred to US Medical facilities on St. John in the event hospitalization is needed and there, US Law concerning medical disclosures holds).
You might want to speak with Cecilia Donegan, a lovely Irish Lass don't-ya-know, at Pro Valor. We had good communications with her and she was a great help. (284.495.1931-voice/fax - 8 AM- 5 PM)