Fairhaven has at least two distinct faces, each of which contributes to its appeal as a cruising destination.


Visiting Cuttyhunk presents the classic paradox of travel to all remote and uncommercial places: how to appreciate them without undermining the very qualities you came to admire.

Woods Hole

Woods Hole is the Jekyll & Hyde of Massachusetts waterways — sometimes a placid and well-marked maritime thoroughfare, sometimes the most dramatic and dangerous mile of water on the coast.

Vineyard Haven

In the age of sail, Vineyard Sound was among the world’s busiest sea lanes. When those vessels needed shelter from hard weather or a foul current, it was an obvious choice – easy to enter and close to their route.

Pollock Rip

Running almost 9 miles from the elbow of the Cape at Monomoy to the northern tip of Nantucket, the Rip is a ridge of shifting sand, cut through with a handful of shifting channels.

Oak Bluffs

Oak Bluffs has unabashedly welcomed summer visitors for over 150 years. It’s hard to visit without getting swept up in the resort-town energy.


Nantucket’s gentle island landscapes, seafaring traditions, cobblestone streets and comfortable sense of wealth make it the Grail of regional cruising.


Its central location in Cape Cod Bay – an easy day from Plymouth or the Canal, from Provincetown, or from Boston Harbor – makes Scituate a nearly automatic stop on any regional itinerary.


Sandwich is two distinct places: the Boat Basin at the east end of the Cape Cod Canal, and the town itself, a mile or so away along the coast towards Provincetown.


After Thoreau visited in 1850, he declared Provincetown “the most completely maritime town that we were ever in.”