We've been heading to Maine most summers for a while now. Out home port is Onset, so we're starting the same as those who wait in our harbor for the Cape Cod Canal current to turn.
One way to Maine from the canal of course is a direct overnight run. We've done it and decided to take a pass. That aside, we have a few rules to help in the process.
Our goal is to make stops based on reasonable day sails. Isles of Shoals makes a good start in Maine, but the trick is getting there. It's a long trek from the Cape Cod Canal, so an intermediate stop helps. But it's possible to make Isles of Shoals in a long day.
It's best to consider how far off the rumb line the stop is. Provincetown, for example, looks to be perfect. It is on the direct course, but it's a long way in (and out) from the anchorage to the tip at Race Point. So a lot of time is lost, unless of course you are cruising and not delivering, and want a place to visit.
We now usually stage from Duxbury which violates that rule but has some advantages for our cruising partners. The current between Gurnet Point and Bug Light, much less Plymouth, is a serious deterrent to this stop.
Back when we were leaving from Onset, we made a number of intermediate stops, depending on time, wind and weather.
Scituate isn't too far in, but has only paid moorings. That would break another of our rules.
Cohasset has a shallow anchorage outside, fine for the prevailing wind and with a view of Boston. Not many boats here.
Great Misery Island, outside of Manchester, can be rolly but has a few moorings to pick up. It's not far to Gloucester (where we've never stopped). You can take the scenic ride up the Annisquam or head out past Thacher Island.
From Isles of Shoals, we've settled on the longish run to Casco Bay, skimming the outskirts to stop at Jewell or Cliff Islands.
From there on, we're really in Maine and can go fast or slow, inshore or offshore.
Begin to laze and enjoy and stop at Harbor Island, Muscongus Bay. Or push it for one more day and go for Tenants Harbor. Be different and head out to Matinicus Island!
One thing to keep in mind is the need for provisions and fuel. After Harbor, we stop at Port Clyde and hit up Linda Bean for both. That night puts us into Penobscot Bay.
There are logs of varying detail on the web at: http://sailonset.com/SailingNE.html.
Here is our sunset arrival at the Isles of Shoals in 2005, having stopped in Cohasset the first night out. Both boats being new to us, it was a doubly-pleasant moment.