The Life Aquatic: Where to Find New England's Classic Yachts

Brine, fine design and elegance intertwine on the New England vintage sailing scene.

When Puritan settlers first eked their way across the Atlantic and onto the shores of Cape Cod four hundred years ago, the identity of New England became inextricably bound to the sea. Cod, tuna and swordfish boats sailed out from Gloucester while whaleboats fanned out across the globe from Nantucket and Martha’s Vineyard. In Boston proper, the commerce of these ships was processed, sold and shipped, while the boatyards of New Bedford and Rhode Island churned out the vessels that carried crews of New Englanders throughout the world.

Though the Cod has dried up, the whale-oil lamps have been snuffed out by electricity, and the boatyards of Bristol make their mark with fiberglass molds, the classic vessels that once dominated Boston’s maritime world can still be found and experienced throughout New England. Both on and off the water, here are some of the best ways to relive the heyday of Boston’s ocean-bound history.

Herreshoff plans 1904


In 1870, a young man from the shipbuilding hub of Bristol, RI, graduated from MIT with a degree in mechanical engineering. His name was Nathanael Greene Herreshoff, and within 20 years he would be designing and building the fastest boats in the world. Herreshoff’s early years were devoted to steam-powered vessels, designing and producing first-of-their-kind iron torpedo boats for the US Navy; as the turn of the century approached, he shifted his growing resources to the production of innovative sailing yachts. If you want to see the boats behind the blueprints, take a trip down the highway to the original Herreshoff Marine Museum in Bristol, Rhode Island, where you can view and explore over sixty restored and preserved boats, ranging from eight-foot dinghies to 75-foot America’s Cup defenders and everything in between.


For an up-close look at the process of designing and building these classic yachts, pay a visit to Herreshoff’s alma mater MIT this fall where they will be displaying a vast collection of plans, blueprints and original photographs of Herreshoff’s historic yachts: "Lighter, Stronger Faster: The Herreshoff Legacy."

The Black Dog Tall Ships


Paper-bound designs reveal what goes into designing a boat and land-bound hulls provide a close up look at what those designs create. There is nothing, however, like seeing those concepts and hulls spring to life where they were meant to thrive: on the water. The annual Herreshoff Classic Yacht Regatta (Aug. 23-24, 2018) brings classic sailing yachts from across the world to compete in two days of competitive sailing on Narragansett Bay and public social events on the shore. When the Herreshoff regatta ends, competitors will point their bows south and sail down the bay to Newport for two more days of classic sailing in the Newport Classic Yacht Regatta from Aug. 25-26, 2018.


There’s a certain feeling, an electric vibration, that spreads through the deck of a yacht when its sails catch the wind and the hull begins to heel to leeward; there’s no place where that energy is better felt than on the deck of a mighty tall ship under sail. Take a trip across the Vineyard Sound to the Black Dog Wharf in Vineyard Haven, where on afternoons and evenings The Black Dog’s 108-foot schooner Shenandoah and the 90-foot Alabama invite visitors to help raise the sails and cruise throughout Vineyard Haven Harbor and the Sound. For those who can’t make it to Martha’s Vineyard, the Liberty Fleet of Tall Ships’ Liberty Clipper and Liberty Star make frequent tours of Boston Harbor per day and even serve as a floating hostel by night.

Schooner in Gloucester Harbor


When the Dorchester Company funded the settling of the Cape Ann (the peninsula where Gloucester sits) in 1623, farming was intended to support the settlement and make back more than their investment in the expedition. However, Cape Ann’s tough, sea-swept soil proved to be less than arable and the settlers were forced to take to the sea, fishing the water extensively until the colony was largely abandoned. A few remained, however, pulling their livelihood from the ocean until Gloucester was resettled and grew to be the fishing capital of New England, a title it holds to this day. Though the harbor is now dominated by the tall bows of steel fishing vessels, the Gloucester Schooner Festival (Aug. 31-Sept. 3, 2018) offers the rare spectacle of a harbor full of tall ships under sail, as schooners from around the world parade and race about Gloucester Harbor.


When the Gloucester colony was first abandoned, it was to present-day Salem that the settlers relocated. It’s fitting then that Salem Harbor is hosting the 36th Annual Antique and Classic Boat Festival (Aug. 25-26, 2018). At Brewer Hawthorne Cove Marina, a fleet of classic sailboats and motor yachts will be moored up along the docks for public tours.

Alex Oliveira
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