What a treat awaits you!!!! If you are a dedicated gunkholer, there are so many little hidey holes, you can anchor out with just you and the ospreys and eagles and when you want to get your exposure to town life, there are the few stops that offer all you could ask for.
You have to stop at Tangier for crab cakes....St. Mary's City for the history, I am eager to travel up the Potomac to visit DC sites...may not appeal to many but I would love to go and not have to worry about traffic, parking, yada, yada, yada. Chrisfield has a wonderful state run marina for a break. I have not been there for a few years so it may have changed but it was a nice respite for us. Irvington, Va is kind of a good spot to stop also. Mobjack Bay is kind of a shallow but interesting area and then the York...can visit Yorktown...then Hampton and you can go to the Maritime Museum in Newport News...that is the best ever for maritime history...worth more than a day's visit. Also Jamestown is a terrific spot you can travel too. I am sure you got the experience of Norfolk and Portsmouth when you did the big trip South. Old Point Comfort Fort is worth a visit. My Dad always said you could spend a lifetime exploring the Chesapeake.
I am so jealous. We did the length of the Bay on a 26 footer years ago and had a ball. Our needs were fresh ice, fresh vegetables and an occasional meal out. The Tides Inn provided free ice and the offer of a car (free if we just put in some fuel and back then that was nothing) and we anchored out! We met so many folks who were so kind and generous it really made the experience a wonderful memory of a lifetime. It is one of the reasons I am eager to go cruisin'. Hope you have the Gunkholer's Guide...very helpful.
lying in Oxford, MD