Hi Dawn. As I recall, you initially posted looking for a cabin or cabins on a charterboat (bareboat or other), and created quite the hubbub among TTOLers in doing so...I can't remember why.

Of course it's just MHO, but maybe you should just dip your toes in the water, and not jump in head first. For example, perhaps you can plan a land-based vacation with your friends on Tortola or Virgin Gorda. You could take a couple of daysails, and maybe even a one or two night overnight sail (yes, there's plenty of small daysail boats and bareboat companies that will do that). If you like it...next year do a skippered bareboat charter. You'll have a whole year to sell some people on the idea, so you can have an entire boat to yourselves.

Failing that, how about trying a 'headboat' first? A headboat is basically a cruise ship - although MUCH smaller. They book people per cabin. It's a great way to be introduced to a destination, without the sadness of a large cruise ship, and the hassles of a bareboat (or the expense of a crewed charter yacht).

Here's one such company, although there are a couple of others:

http://www.islandwindjammers.com/virgin-islands-cruises.aspx

Good luck, and have fun in your quest!