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Eastern Seaboard
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New England
Charm
At last we reach Boston Harbor and its islands. Boston Harbor is older than most countries. It’s gritty. Polished – lightly – for the tourists, but without losing its edge. There’s the glint of glass skyscrapers, sure, but they’re sitting awkwardly next to 18th-century brick buildings. It’s a city that’s never quite made up its mind about whether it wants to be New York’s cooler cousin or a living history museum. Then there are the islands: little green blips like Spectacle, Thompson, and George’s that offer refuge from the city’s pace, with forts, trails and beaches. It’s authentic, and all the better for it.
Waypoint 7
Boston Harbor
The penultimate waypoint is Provincetown (or “P-Town,” as it’s known by those who wear feather boas unironically) is a glorious explosion of art, colour, and character perched on the edge of Cape Cod. It’s one of the very few places in the States where the weird, the wild, and the wildly wealthy have all agreed to share a bit of sand and sea without shouting at each other. It’s part art colony, part fishing village, part social experiment—and all of it works in a glorious, slightly chaotic way. Climb the Pilgrim Monument, explore Herring Cove Beach, or go whale watching.
Waypoint 6
Provincetown
This is where the journey peaks in old-money splendour: an island where cobblestone streets and historic whaling cottages transport you back in time. It’s got taste. And manners. Even the seagulls seem well-behaved. This is not a place where you show off your wealth by revving a Lamborghini. You park your battered car outside a house with perfectly weathered shingles that’s been in the family since the Civil War. Explore the Whaling Museum to delve into the island's rich maritime history, or visit the Sankaty Head Lighthouse for breathtaking coastal views. It’s charming, peaceful, and absurdly picturesque.
Waypoint 5
Nantucket
Known as Amity in the 1975 film Jaws, it’s less workaday than depicted. Martha’s Vineyard exudes charm and sophistication It’s a place where people ‘summer’ rather than merely spend their vacation. The island is a patchwork of little towns, each with its own flavour. You can cycle the entire island, get lost in farmers’ markets, eat lobster rolls, or browse art galleries. Strolling through Edgartown, all white picket fences and centuries-old captain’s houses, you half expect Chief Brody to burst onto the street shouting about closing the beaches. It does add a certain thrill to paddleboarding.
Waypoint 4
Martha’s Vineyard
Today we’re dropping by Cuttyhunk Island, a tranquil retreat known for its pristine beaches and abundant marine life. Cuttyhunk is the westernmost of the Elizabeth Islands, a chain of rugged, mostly private lumps of land owned by people who have last names that sound like Ivy League libraries. But public Cuttyhunk is the exception. When you arrive, it feels less like entering a port and more like stumbling into someone’s well-kept secret. There are no cars and no boutiques. In fact, there’s not much to do here except eat fresh local oysters and congratulate yourself on your life choices.
Waypoint 3
Cuttyhunk Island
Next is Block Island, anchoring at Great Salt Pond. At only about 7 miles long and 3 miles wide, it’s one of the most charming, gloriously old-fashioned specks of land in the United States. The island runs on what one can only describe as “lobster time.” People are either going to eat it, catch it, or talk about how good it was last night. Explore the island's scenic trails by bicycle, visit the iconic Southeast Lighthouse, or relax on the beaches. The town of New Shoreham is basically a handful of weather-beaten buildings which have probably looked exactly the same since Roosevelt was president. There’s something refreshingly unbothered about the place.
Waypoint 2
Block Island
We’re beginning our journey in Newport - the spiritual home of American yachting. Back in the Gilded Age, the great and the grotesquely wealthy (think Vanderbilts, Astors, people whose surnames sound like investment banks) descended on this seaside town and decided to build summer ‘cottages’ not too far from New York. Cottages, that is, roughly the size of Versailles. The opulent Breakers mansion is worth visiting. Then explore the historic waterfront – packed with sloops and schooners. As evening descends, dine at one of the harbour’s upscale restaurants, savouring seafood delicacies.
Waypoint 1
Newport
Welcome to old America. The kind of place where the
towns weren’t designed around cars but horses, and
the harbours have seen everything from pirate ships
and whaling vessels to America’s Cup contenders.
The coast hugs you like an old friend. It’s
glorious, elegant – and exactly how
summer should be.
By sharing some Members'
itineraries, we're helping others unlock
their yachts’ full potential, reducing crew turnover
and making ownership a more rewarding experience.
Country(ies):
United States
Time zone(s):
Winter:
EST (UTC-5)
Summer:
EDT (UTC-4)
Currency(ies):
United States Dollar (USD)
Temperature:
February:
4°C (40°F)
August:
18°C (64°F)
Sunshine:
February:
6 hours
August:
9 hours
Humidity:
February:
62%
August:
71%
