I just used Jerry's car rental, near West End. Good experience. Agree to skip St Johns because of the logistics hassle. Do a beach day at Smuggler's Cove and visit Patricias. Lunch at Indigo Beach House in CGB. For a nice dinner, try the Sugar Mill. (many of these recommendations came from Manpot and were on point). Long Bay Beach Resort has a nice bar right on the beach. If you do a private boat charter I would skip Jost Van Dyke. Instead, take the ferry over to JVD from West End and spend a full day over there.