There's an art to sailing for sure. I'd suggest a Power Cat (they have a nice set up too) and hire a Capt for the first day day. Take some on-line classes before you get there. Plenty of room in the Caribbean Sea to move around. You'll be fine. The navigation tools on board are very user friendly, you will be amazed. Use mooring balls instead of anchoring over night (get to your next night destination early). The charter base is always a phone call away. By the end of your stay you'll have that thing doing 360's on a dime.

Be sure it has a generator, a/c, a water & ice maker. Don't cheap out here. It will save you a ton of time.

Lastly, plan your nights accordingly. Willy T's on a Saturday night was everything they said it was. A Tuesday, not so much. We had a blast at Foxy's on a Friday night but I hear Sunday is locals night and can get rowdy, so we were sure to be elsewhere. Enjoy.