I took several sailing classes and spent as much time sailing as I could for the year leading up to my first charter. As you might expect, most of that sailing was in small boats -- Sunfish, Deisgner's Choice, and Flying Scot. Twanger's point is right on - the big difference with a big boat is learning how the systems work. I took a class from Annapolis Sailing School - I think it was called "Preparation for Bareboat Chartering" that focused on the various systems and how they work. I also took another course from them just to get some more time on a big (30+ foot) boat. That also provided some "credible" documentation to back up my kind of slim sailing resume.

My first charter, (a Beneteau Idylle 43) The Moorings put a captain on board with us. The deal was that if he felt comfortable that we knew what we were doing, we could drop him off before the end of the first day. We sailed out of Road Harbor and got under sail. The Captain threw a cushion overboard and we had to do a man overboard drill. We succeeded and he felt comfortable that we were relatively competent (I don't believe any of the crew had any sailing experience at the time so I had to direct them through the man overboard drill). We dropped him off at the Peter Island ferry dock and gave him a few cold beers for his ride back.

We had an awesome time and went back 4 more times.