Southern Chesapeake Bay Marinas/Boatyards
I just couldn't resist responding since most of the responses were from areas further north in the Bay. The area around Stingray Point, Middle Peninsula, is a great cruising area and one of the widest parts of the Bay. Has a large number of rivers and creeks to explore and anchor out. Also has a large number of excellent small marinas and great boatyards. Norton's Yachts is the Hunter dealer (with absolutely great staff and mechanics) and can give you lots of advice on where to cruise as well as provide advice on repairs and storage (take a look at their website). This area is not conjested (primarily sailboats and small fishing boars) and is within easy cruising distance of the eastern shore (about 3 hours). Also, about equal distance from Annapolis and Hampton Roads (great cruising destinations. There are a number of yacht clubs in the area with members who would be happy to have you cruise with them (I am the Treasurer of the Stingray Harbour Yacht Club of about 100 members and would be happy to send you more information.) Major airports are within an hour's drive in either Richmond or Norfolk areas. Also, closeby are land destinations like Williamsburg, Bush Gardens, Norfolk Shipyards, Yorktown, Richmond, Kings Dominion, Washington, etc. I know you will enjoy the Bay and the summer cruising it.