Ansley W. Sawyer wrote:
Richard,

I would suggest a route that approximates the following, it presumes about
fifty miles a day with anchorages that are not too far inland.

Boston to Kittery, Maine
We frequently stop here, anchoring or getting a mooring in Pepperell Cove.

Jewell Island (east of Portland, ME)
Jewell is certainly a lovely spot, one of the "not to be missed"
places in Maine. However, it is a tight spot, a bit of a challenge to
anchor in, and problematic in thick fog, which is always a possibility.

As a target for the end of the day, Richmond Island, just south of
Cape Elizabeth is better: there are easy anchorages on both sides of
the breakwater, so its a good refuge in both NE and SW blows, and
there are no major hazards getting in or leaving. And, if I'm not
mistaken, our Roger Long is the Harbormaster.

If you leave from Cape Ann, you might be able to reach Richmond I in
one hop.

Port Clyde

Northeast Harbor
Another great spot. If you want a slip or mooring, call well in
advance. There are many alternatives nearby, Southwest Harbor, Somes
Sound, etc.