Interesting that I am doing the same thing. Leaving FL in May and plan to cruise up the coast for 3 months. We are going to spend alot of time in the Chesapeake Bay area and visit DC. Hope to spend several days in the museums, etc. Will also go to NYC for a couple of weeks. Sailing will constitute about 50-60% of the trip with the remainder doing daytrips onshore, etc.
The difference in our trips may be that a southern boy is exploring the NE.
You will probably be more interested in southern waters. A person could spend months exploring FL and Keys.