We've used a day captain to start a couple of our trips. They'll help familiarize you with the boat, help "relieve" stress handling a new boat at the marina and during the brief 2-3 hour sail if there are any issues/quirks with the boat the captain can help. We used a day captain at TMM aboard Mardi Gras, he left the driving to me and instructed a couple first timers we had on their responsibilities, i.e. raising main, tying/stowing fenders, operating the windlass, hooking etc. We sailed to Peter and set the hook then moved to a ball in Sprat Bay where we dinged the captain in to catch the ferry back to Road Town. Literally All systems checked, no questions. Money well spent for us! You are going to be fine, enjoy the planning! <img src="http://www.traveltalkonline.com/forums/images/graemlins/toast.gif" alt="" />