Not sure how long you'll be on the boat but Anegada doesn't have to be a two night stop. The sail really only takes about three hours so you could easily take off after the first night if it's not your thing. For us, one day on Anegada is enough, but I know others could spend their entire charter there. I do like the sail to Anegada and back - just set the sails, let a fishing line out and relax. If you are interested I'd say yes to Anegada and just stay flexible as to whether you stay one or two nights.

As far as making Leverick on the first night, it probably depends on how quickly you get off the dock. Pre-provisioning would help and having a captain might expedite the process if he is known by the charter company. Also, he MIGHT be able to take you through Mosquito Cut rather than all the way around to the Northern channel. That could trim almost an hour off the trip.