The harbor is convenient; the setting is beautiful; the protection is good.
The entire passage, generally referred to as the Annisquam, is frequently an attractive alternative to the trip out around Thatcher’s Island.
The cove offers adequate protection for most summer conditions, good swimming, and a view of the Atlantic over Brace Rock that can be striking.
With flowers that line its walking trails and beautiful slate and shell beaches, Bumpkin Island is the ideal place to relax in nature.
Cape Cod Canal
With its impressive engineering, its succession of bridges, the concentration of traffic, even the streetlights lining its banks, the Canal possesses a quirky industrial charm.
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.
Fairhaven has at least two distinct faces, each of which contributes to its appeal as a cruising destination.
With its location halfway between Annisquam and Rockport, Folly Cove is a convenient stop on most Cape Ann itineraries.
The graceful granite archways of historic Fort Warren will greet you as you arrive for your visit to Georges Island. This Civil War-era fort is the main attraction of Georges Island and it is sure to bring out your inner history enthusiast.
Gloucester has a vibrant shoreside community whose cultural origins span the maritime world. It’s a particular favorite of ours when the weather turns dismal.
This perfect little gem of a harbor sits near the Buzzards Bay entrance to Woods Hole – at the nautical crossroads of southern New England.
Isles of Shoals
What’s perhaps most remarkable about the Isles of Shoals today is how easy it still is to get that sense of being ‘apart from the main’ here.
The Piscataqua River is a force of Nature as imposing as anything on the coast from Pollock Rip to the Kennebec.
The dramatic shorelines near Magnolia are only a short diversion from the routes along Cape Ann.
Inside the slim well-protected harbor may be the prettiest shoreline attached to a full-sized town in all New England. The yacht club, private boat houses, boat yards, town docks and thickly placed moorings make an unambiguous impression.
From its beginning as a fishing outpost, through its years as America’s premier yachting harbor, to what is now the North Shore’s least accessible commuter town, Marblehead has evolved with its face to the sea and its back to the land,
Marion offers a lovely, well-protected harbor and streets that are uniquely attractive among Massachusetts’ old coastal towns.
With just one street of small shops, surrounded by beach, dunes, grass, mixed forest and vast saltwater ponds, Menemsha feels seductively like the edge of the world.
The Misery Islands supposedly got their name after a local shipbuilder, harvesting timber, spent three days stranded by a December storm in the 1620s. We’ve never visited the islands in December, but from May through October, we’ve found them unanimously pleasant.
Nantucket’s gentle island landscapes, seafaring traditions, cobblestone streets and comfortable sense of wealth make it the Grail of regional cruising.
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.
The channel into Onset doesn’t feel as tight as the chart suggests, though, and at the end is a quiet, Victorian-inflected seaside resort.
The harbor’s size, its quick access to Buzzards Bay, and the century-old tradition of the New Bedford Yacht Club station have made it a popular destination since yachting took hold here at the end of the 19th century.
Both serene and historic, Peddocks Island is known for its rich biodiversity and is home to Fort Andrews.
Plymouth has a working waterfront in the modern sense: whale watching, charter fishing, restaurants, motels and shops all cater to the town’s visitors.
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.
After Thoreau visited in 1850, he declared Provincetown “the most completely maritime town that we were ever in.”
For a cruising sailor, Quicks is rarely on the way to anyplace except Menemsha, but it is a lovely and remote little stretch of water.
This legacy of slow development, punctuated by a significant grant of open space, leaves Quissett’s waterfront pleasantly sparse and unhurried.
The harbor’s placid shorelines and quirky, down-the-rabbit-hole entrance make it worth a visit, especially if your schedule allows for time to get off the boat and explore the area by dinghy or on foot.
Rockport seems to exist just this side of magic realism. A narrow cut between rocky headlands provides the setting; a man-made breakwater forms the harbor.
The most famous voyage into Salem harbor is that of Nathaniel Bowditch, commanding a three-master homeward bound from Sumatra. Crossing the rock-strewn waters of Salem Sound, even in clear weather, should inspire appreciation for the navigators of Bowditch’s era.
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.
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.
With panoramic views of the Boston Harbor and an accessible lifeguarded beach, Spectacle Island is ideal for outdoor adventures or a relaxing day by the sea.
Nowadays the cove, like the rest of the island, is largely uninhabited, the lighthouse is automated and the (relatively) few boats transiting the Sound rarely need a sheltered anchorage to wait for wind or tide. Tarpaulin Cove is left mostly to daytime visitors.
Thacher Island gets its name from one of the earliest and still more poignant shipwrecks on the Massachusetts coast.
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.
If you’re passing by with time for lunch and a swim, or you need to get the kids ashore, stopping here can be the perfect answer.
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.
The way into Worlds End is narrow and a bit twisty, but the channel intuitively follows midway between the two shores and it’s well marked, though unlit.