I am starting to plan the season's adventure: departing from Toronto I think around mid-June, intending to arrive in the mid-Maine coast by August or September. What should I not miss on the way? I am not sure we have enough time and/or the adventurousness to go up to Newfoundland, probably sticking to the south coast of the Gulf. Mentioned so far generally speaking:

1000 Islands
Montreal
Quebec
Bras d'Or Lakes

What are your favorite places, anchorages, towns along the way? What to skip, what to hit?

Also, what is the best time of year to arrive at the various places, and why?

We will probably be spending a good part of next season in Maine, so I am most interested for now in the Canadian Maritimes.

6.5' draft so can't go where the water is super thin....