We slip at Cutter Marina now and previously West Shore Yacht Center. Cutter is a nice spot. Quite calm location, even when the wind is blowing. Little to no current to worry about when docking. On weekends, the no wake zones extend for quite some way and it takes about 20 minutes to get through that, but I find that is time well spent stowing things and preparing to get underway at plane. The Middle River is a good base to reach popular destinations, such as Fairlee Creek, Rock Hall, Kent Narrows, Annapolis, Baltimore, Sassafras River, etc. (I guess I could go on and on). If you didn't want to go far, go on the hook at Sue Creek or Frog Mortor Creek, etc., and of course, Harte Miller Island. I think they are a bit pricey, but after experiencing the rock 'n' rolling at West Shore, the money's worth it to me. If you slip over on E dock with the finger piers, you'll save a bit over A or B dock. They have some floating docks, but I understand they are all filled and there's a waiting list.
As for the land-based area, plenty of places nearby -- 3 West Marine stores within an easy drive; a couple of nice restaurants, 7-Eleven for last minute stuff, Mars grocery store, etc.