Keeping in mind that I like to keep moving (but my wife less so). I'm thinking somewhat along these lines:

Leave SW Harbor 6/16
6/17 - 6/18 Bar Harbor
6/19 - 6/22 Eastern Bay/Roque Island area
6/23 - 6/24 NE/SW Harbor
6/25 - 6/28 Blue Hill Bay area
6/29 - 7/3 Isle Au Haut Bay area
7/4 - 7/8 Penobscot Bay area
7/9 - 7/10 Casco Bay
7/11 - 7/12 Portsmouth
7/13 - 7/15 Gloucester/Marblehead
7/16 - 7/19 Boston

Leave boat in Boston for a couple of weeks, then return to continue south.

Any opinions of the sort "don't bother with that" or "don't miss this" or "spend more time here and less there" would be greatly appreciated. Of course adjusted as we go for weather and whim. The distances don't seem to be great, so even on sailing days there should be time to look around a bit. Boat draws 6.5 feet so some places seem kind of thin.