New England — Newport & the Islands
Gilded Age lawns run down to the harbour that defended the America's Cup for half a century. Sail out past the mansions and the islands begin — Cuttyhunk, the Vineyard, Nantucket, and Maine beyond.
Newport is where American yachting keeps its capital: the America's Cup was defended off this shore from 1930 to 1983, the New York Yacht Club holds court at Harbour Court, and the 12 Metres still match-race past the mansions. From Brenton Cove the islands unfold in easy day-sails — the Forbes family's private Elizabeths, Edgartown's white whaling streets, Nantucket behind its little lighthouse. The water is cool, the oysters arrive by boat, and in August the whole coast goes racing. Those with a second week point the bow down east to Maine.
“Australia took the Cup in '83; Newport kept everything else.”
The gallery
Signature anchorages
The Gilded Age coast: 12 Metres match-racing off Newport's mansions, oysters shucked at the rail in Cuttyhunk, and the whaling harbours of Edgartown and Nantucket a day-sail apart.
- Brenton Cove, NewportThe calm bight below Fort Adams, in the lee of the cliffs with the New York Yacht Club's Harbour Court on the rise above; tender across to Bannister's Wharf for dinner.
- Hadley Harbor, Naushon IslandA landlocked pool off the Forbes family's private island — no town, no lights, total quiet a morning's run from Newport.
- Cuttyhunk HarborThe one public island of the Elizabeths; the floating raw bar circles the pond at dusk, shucking island-grown oysters at your rail.
- Edgartown Harbor, Martha's VineyardProtected water between the whaling captains' white houses and the empty beaches of Chappaquiddick; the lighthouse marks the way in.
- Menemsha Bight, Martha's VineyardAnchor off the fishing village that played Amity in Jaws — lobster comes straight off the boats, and the sunset is the evening's entertainment.
- Nantucket HarborRound Brant Point into the old whaling port — a berth at the Boat Basin in the middle of town, or anchor up-harbour off Coatue's empty sand.
- Pulpit Harbor, North HavenPenobscot Bay's signature shelter — enter past the osprey nest on Pulpit Rock into spruce-and-granite stillness; Maine, distilled.
The scene
Newport Bermuda Race
A fleet of 150-plus boats starts off Fort Adams on 19 June 2026, bound 636 miles across the Gulf Stream for Bermuda — watched best from your own foredeck.
Newport Charter Yacht Show
The American charter fleet on parade at Safe Harbor Newport Shipyard, 22–25 June 2026 — sailing and motor yachts from 50 to 200-plus feet, brokers only.
Newport Folk Festival
Three sold-out days at Fort Adams, 24–26 July 2026. The stage sits on the harbour's edge — the smartest seats are on boats anchored just off it.
12 Metre World Championship
The America's Cup boats of the Newport era race for their world title off the town again, 5–9 August 2026 — Courageous, the 1974 winner, still among the fleet.
Nantucket Race Week
Nine days of island racing from 6 August 2026, closing with the 54th Opera House Cup on the 16th — a Sunday of wooden classics under full sail.
Amity Island, in fact
Spielberg shot Jaws on Martha's Vineyard — Quint's shack stood at Menemsha — and HBO's The Gilded Age films inside The Breakers, Marble House and The Elms.
Table & stay ashore
Clarke Cooke House — the Candy Store
A 1780 merchant's house moved beam by beam to Bannister's Wharf in the 1970s; dinner upstairs, then down to the Candy Store bar — Newport's yachting salon since the Cup years.
The White Horse Tavern, Newport
Pouring since 1673 under America's oldest tavern licence — once owned by the pirate William Mayes — in candlelit colonial rooms a short walk from the harbour.
Topper's at The Wauwinet, Nantucket
The island's grandest table, at the quiet head of the harbour; arrive by the hotel's launch across the bay. The cellar has held Wine Spectator's Grand Award since 1996.
Straight Wharf, Nantucket
Harbourside seafood institution since 1976, steps from the Boat Basin slips — the town's summer dining room.
Castle Hill Inn, Newport
Relais & Châteaux on a private 40-acre point at the harbour mouth; take the lawn at golden hour and watch the fleet come home.
The Wauwinet, Nantucket
Nantucket's only Relais & Châteaux, strung between bay water and ocean beach at the far, quiet end of the harbour.
A week, sketched
Newport — board at the Shipyard
Step aboard at Safe Harbor Newport Shipyard, lunch afloat, then a slow lap under the Gilded Age mansions to an anchorage in Brenton Cove.
Newport — the Cup and the cliffs
Race an America's Cup 12 Metre in the morning, walk the Cliff Walk past The Breakers after lunch; dinner at the Clarke Cooke House, nightcap in the Candy Store.
The Elizabeth Islands
Cross to Hadley Harbor's landlocked calm off the Forbes islands, then on to Cuttyhunk, where the raw-bar boat shucks oysters at your rail at dusk.
Menemsha & the Gay Head cliffs
Round to Martha's Vineyard's wild western end — clay cliffs glowing at Aquinnah, lobster straight off the fishing boats, sunset at anchor in the bight.
Edgartown
A morning on Chappaquiddick's empty beaches, an afternoon among the whaling captains' houses; the lighthouse lights your way back aboard.
Nantucket
Cross the sound and round Brant Point to a berth at the Boat Basin; go by launch up-harbour for dinner at Topper's at The Wauwinet.
Great Point & wheels-up
Beach morning along Coatue toward Great Point, then a car to ACK minutes from the dock — or point the bow down east for a Maine week.
Pair with
Plan this water
New England — Newport & the Islands
America's yachting capital and its islands: 12 Metres off the mansions, oysters shucked at the rail in Cuttyhunk, Nantucket a day-sail east. June to September.