What kind of boating experience are you looking for when you get to your boat? The Bay offers a range of opportunity from city skylines, to quaint little towns, to some beautiful rural areas.
Where you locate your boat will impact the kind of experience you have. Annapolis, Baltimore or the Norfolk area offer a lot of land based attractions in addtion to the bay, but come with the attendant crowds of people. Other areas offer more of a get away.
My boat is at Deltaville, VA which would probably be an hour from Norfolk airport. The area has several experienced boat yards, some decent places to eat and not much else. Large vessel traffic in the area is less of a concern than around the big port cities. We really enjoy the fact that our "home away from home" is in an area very different from our home in Northern Virginia.