Of the many times I've cruised Maine (and you have thousands of options and itineraries), one thing we did one year which worked out well is to go as far east as you're going to go first...e.g., Mount Desert and cruise harbor to harbor back (which will be more or less upwind). That way, you don't have a long slog at the end of the trip, and you can go upwind a small piece at a time. The wind in Maine is prevailing Southwest. If it's light, your boat will be better, etc. Anyway, one man's opinion.