Thinking with fair weather:
Day 1- to eastern ct
Day 2- stonington ct (a favorite)
Day 3- Marion or Onset
Day 4- Cape Ann area (Gloucester or Anasquam depending )
Day 5- Portland
Day 6- rockland

I could break that into 2 long weekends to stage the boat using one-way car rentals. No more than 65 or 70 NM per day, which is very reasonable assuming light winds and 6k planning speed (we motor at 7.5-8). Then we could spend a few days sailing around Penobscot before working our way back...

OTOH, the area from Cape Ann north looks very interesting on the charts, and maybe we should just explore that without skipping over? Save eastern Maine for another time?