Ever consider doing a sailing course? there are a number of live aboard sailing courses in the BVI/ USVI that takes you around to all the great sights

The costs are a little more expensive but you get ASA 101/103/104 so that you can sail on a smaller monohull or Cat the next time you come down.

Did this three years ago, loved it! Since then we have done 2 successful bareboat cruises in the BVI and now are planning another sailing course in Grenada to really get some open water experience.