heading North (reverse order if heading South), Onset, thru the CCC, then you have a choice of either going to P-Town (nice stop, good anchorage, but
makes long hop the next day) or Plymouth or Scituate (the latter means paying for a mooring), then on to Catumet. From P-town or Catumet (or Scituate or
Plymouth) head to Gloucester.
Totally ignore the advice of anyone who says you should take the canal (ironically, for the very reasons they recognize). Head outside around Cape Ann
to Isle of Shoals. Make sure you pick up a mooring in the north side of the tiny harbor - that way you can say you've arrived in Maine. From Isle
of Shoals a very long day passage would take you to Peaks Island. Or, you could stop at Wood Island Harbor (there's often not room to anchor there so
you might have to pick up a mooring) or continue to Richmond Island Harbor or Seal Cove (depending primarily on the wind direction) and continue
to Peaks Island the next day. If you really want to go slow, after having anchored at Peaks take the ferry into Portland and spend the day looking
around.
From Peaks, head to The Basin in New Meadows River - although there are other nearby anchorages as well you might consider. Sebasco Estates
is nice but you'll have to pay for a mooring.
From The Basin, head to Boothbay Harbor. From Boothbay, head to Tenants. Head North to Rockland - you are now in the promised land.
Many choices from here, heading East.
The first time I went to Maine I got to Rockland and was considering where to go next. A fellow cruiser said "You MUST go to MDI!". It was
excellent advice which I followed.
Jerry