So many choices!
It comes down to a balance of how far you are willing to drive, the size of your wallet, and your sailing interests.I live in Annapolis and work in DC. We keep our Hunter at a marina a 5-minute walk from our house. Annapolis is a great city, very busy on the sailing front like Newport, but not for everyone. It's kind of like living “inside the beltway” for sailors.We pay about $4,500 for a 40' slip in Annapolis (you can spend up to twice that for the same sized slip at other marinas, depends on amenities, e.g., tennis courts and swimming pools). Annapolis is about an hour from DC. We used to keep our boat in Solomons Island, about an hour south of Annapolis, at 60% the price of what I pay in Annapolis. And before that, we had our boat in the Rappahannock River area, a 3-hour drive from DC, for about a third of the price in Annapolis. I sailed a Catalina 27 out of Herrington Harbor (North and then South) some 18 years ago, and that's a great location too. All of these are wonderful Chesapeake sailing venues, IMOIf I were to pick a marina for you without knowing any more detail, I'd head for Herring Bay as others have mentioned here. My pick would be Herrington Harbor South. It's central and within easy reach of many Bay attractions, dock fees are reasonable, has excellent boat services, racing/cruising clubs, and it's within easy reach of DC and suburbs. When you leave the marina in your boat, you are almost instantly in the Chesapeake Bay instead of having to face a slog down a river to get to the Bay. Great access!