Some would have you go direct from the Cape Cod area up to Penobscot Bay. If you wish to experience southern Maine, here are some suggestions working north;

Isles of Shoals or Portsmouth harbor. The shoals usually have moorings or you can drop anchor in the right spots. A nice island adventure. Contact me direct if going into Portsmouth for local river data.

Biddeford Pool is not to be missed, followed by Richmond Island (sshhh, don't tell anyone about that one). Next on to Portland where docking at DiMillo's is a nice in-town experience. Heading north, make sure to traverse Junk of Pork. It's nothing exciting, just a nice passage through a reef strewn but clearly marked area.

On to the folks further north........