Experience and Crew Required for Chartering
I just returned from BVI (sunsail) on a 40-footer with me and my wife. The two of us had no problems anchoring and mooring all around the islands. While I''ve been doing day sails for years, my wife has only 2 years under her sail belt -- we had never done overnights. It was just fine.
If you wish, you can often take a skipper for one or two days just to get comfortable on the boat, then drop him/her off.