Undoubtedly, one of our favorite places is Shelburne Nova Scotia which is 36 hour passage from Provincetown. The town was formed after the American Revolution when the Loyalists fled to a safer Nova Scotia and founded Shelburne. There are many buildings well over a hundred years old, included the cooperage, the dory factory, and the bed and breakfast. We called the Shelburne Harbour Yacht Club (SHYC) our home for nearly a month. The town is a mixture of history, maritime lore, and small town commerce. The SHYC is the social hub for many, both mariners and landlubbers alike.
Then there was Hurricane Arthur which visited Nova Scotia while we were there. For the first time, we left the boat on a mooring and took refuge in a cottage which allowed Sammy Jane to hunker down. The storm (a low Cat I) was kind to the vessels on SHYC moorings but not so much to the town. We heard shingles pop off the yacht club and felt the building swaying in the gusts. Much of the town was without power for over a week.
Another great place is Somesville, Mt. Desert, Maine which is located up the Somes fjord. The beauty of Somesville is in the people, the nature, and the convenience. We were anchored for a couple of days when a local couple came up and offered us two lobsters for free. We later visited his house (Mount Desert House) where we treated royally. Never had we experience the bounty of nature here. We would see bald eagles nearly every day while seals would 'go fishing', and the cruisers would do their kayaking. The village provides a dinghy dock for us visitors which is near the main road and a bus stop. From the free bus, you can travel virtually anywhere in Mt. Desert ... and we did.
We were surprised that we liked the big city of Portland Maine as it is big. But it is diverse in every way imaginable. It is has an accommodating though sometimes rolly anchorage. They also have a great bus system which we used often. We were there during the annual Lobster Feast which was a hoot. Other great places up North include Booth Bay, Gloucester, Onset (though the pizza was not good this time), and Port Washington.