New England Charter Itinerary

New England Itinerary

New England Yacht Charter
This is where American yachting began. Newport held the America’s Cup for fifty-three years, and the whaling money that built Nantucket and New Bedford came out of the same water.





The islands lie close together and the passages are short, but the sailing is real ’ fog, a four-knot tide through Woods Hole, and a southwesterly that fills in every afternoon like a timetable. In between: cobbled streets, grey shingle, lighthouses, and lobster landed that morning.





Every route we shape is a starting point, not a fixed schedule. Stay a second day where the light is right, move with the weather, or follow a captain who knows the cove worth the detour. That freedom is the point of chartering. What follows is one considered way to read New England; the rest we tailor to you.
Day 1

Newport

Newport’s harbour is still the best on this coast and the Cliff Walk runs behind the Gilded Age mansions that the Vanderbilts and Astors called cottages. Tour The Breakers if you want the full absurdity. Then the waterfront, a dark and stormy, and dinner looking out at the moorings. The town has never stopped being a sailing town.
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Day 2

Block Island

Twelve miles offshore, Block Island keeps four hundred foot bluffs on its southern shore and forty percent of its land under conservation. Hike the Greenway, cycle to the Mohegan Bluffs, and anchor in the Great Salt Pond, which is nearly landlocked and holds a few hundred boats without feeling crowded.
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Day 3

Martha’s Vineyard

The Vineyard is bigger and quieter than its reputation. Edgartown is white clapboard and whaling captains; Oak Bluffs has the gingerbread cottages of a Methodist camp meeting. Cycle the flat lanes, swim at South Beach where the Atlantic arrives properly, and eat somewhere with a view of the fishing boats.
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Day 4

Nantucket

Thirty miles out to sea, and for a few decades the richest town in America on whale oil alone. The cobbles were ballast; the houses were profit. The Whaling Museum is superb and unsparing. Walk the cobbles, eat a lobster roll on the wharf, and watch the sun go down over a harbour full of masts.
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Day 5

Provincetown

Round the hook of Cape Cod to Provincetown, an artists’ colony for a century, a Portuguese fishing port for longer, and the actual first landfall of the Mayflower. Dunes behind the town, whales feeding on Stellwagen Bank offshore. The galleries are good and the evening is lively.
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Day 6

Montauk

West along the outer beaches to Montauk, at the far end of Long Island ’ a fishing village that the Hamptons reached but never quite subdued. Surf Ditch Plains, walk out to the lighthouse that George Washington commissioned, and drink somewhere with sand on the floor. The striped bass fishing is exceptional.
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Day 7

Return to Newport

A last reach north-east across Block Island Sound with the sou-wester on the quarter, which is the way this coast is meant to be sailed. Newport comes up in the afternoon, the bridge, then the harbour. Seven days, two states, and a great deal of the history of American sailing.
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New England Yacht Charter Enquire

Enquire about chartering in New England to receive current yacht availability, seasonal guidance and expert insight into the cruising areas, anchorages and experiences that best fit your preferred style of charter, creating a clearer route to the right itinerary.