Thanks for the tips. I spent hours last night on google earth, Navionics and Active Captain stumbling upon many of the things you recommended, glad to get confirmation that they are worth visiting. I don't know why, but I just love taking my boat places where boats like mine are uncommon. We just barely fit under countless bridges on the west half of the Erie Canal last year and turned a lot of heads in the towns we passed through. Was great fun.
Hope you have a great time on the Downeast Loop, that's in our plans as well, not sure when though. I do plan to learn some conversational French first though, I've spent time in Rural Quebec, French parts of rural Ontario, and a lot of France; and I really regretted not speaking the language. I think French would be very useful around the Gaspe Peninsula. Speaking of the Downeast Loop, Hanging a left on the Richelieu or going straight to 1000 Islands has got to be a tough call. Both routes to NYC are really special...