I'd also stay close to the western shore. If there is any westerly component to the wind, the shore should keep the waves from building up too much. The bay really does open up in Virginia. If you got out in the middle of it in bad conditions, you might have to look at your gps to convince yourself that you hadn't accidentally wandered into the ocean. There are also lots of good anchorages on the western shore in Virginia.
I made the trip from Baltimore to Deltaville last March. It was a lot of fun, but the main difference is the amount of daylight hours March versus November. It gets downright cold at night on the water in winter. I'd have a good sleeping bag too.
Gemini Catamaran Split Decision