You're breaking it into two trips and you'll have the luxury of ample time. I don't think you can beat basing out of Rockland. You're on the western edge of Penobscot Bay with likely a reaching wind just outside the harbor that will take you to more destinations(eastward to the beautiful MDI area as Todd mentions) than you could use in years.

All the trans. options are available and the road distance to Southern NE is a good compromise. Many options for moorings to look into were already mentioned.

I don't personally have experience with Rockland rental moorings, but as you get closer Craig, let me know if I can help you with any local knowledge.