I don't mind skipping pretty much everything south of Penobscot bay and could run straight through to Boston I suppose. Some seem to think Gloucster and the Marblehead/Salem area worth a look. Portland and Portsmouth would be just places to stop. I'm not sure I could get through the canal to Gloucester, chart says 6.5 ft in 2002 and we draw that at least. Also my air draft is 64.5 plus the antenna and windex, bridge is supposed to be 65 ft., not sure I would have the balls. Isle of Shoals looks intriguing, good anchorage there? Monhegan also, but that anchorage sounds very dicey.
I'll take a look at revising my planning. I going to save all these suggestions for consideration!