Welcome to Sailnet, glad the have you with us. The Chesapeake Bay is indeed a good place to consider. Lots of great sailing and towns to put into. The city of Annapolis is where I would recommend you look into. It's the sailboat capital of the east coast in my mind. There are many full srvice marinas there that would suit your needs and well as many ship's stores and restruants. You might try searching Google for marinas in that area. best of luck to you and again welcome.