Tenants to Casco, but maybe better to go from Rockport or Tenants to Boothbay to make it easier. Casco Bay to Portsmouth also about the same but there doesn't seem to be any good stopping place along the way. Cape Porpoise Harbor, maybe? Others look pretty shallow. With good weather, 60 miles is not too bad for us. Or maybe skip Portsmouth (doesn't seem to have much to offer) and go overnight to Gloucester? That should be easy in anything but a south wind.
I've got about 10 days in Penobscot and Isle Au Haut areas. Could skip going northeast I guess, but I'm told its worth a look.