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
Jewell Island (east of Portland, ME)
Port Clyde
Northeast Harbor
Cutler
North Head on Grand Manan
Digby or Westport on Brier Island, end of Digby Neck (depending on where in
Nova Scotia he wants to end)
Yarmouth and then points east

I have been to all of these places. Email if I can help.

Cheers

Ansley Sawyer
SV Pacem