Nantucket location work ran in September 2025, which is why the island looks like itself rather than like Rhode Island pretending. Several of the places on screen are real, open, and reachable by anyone with a ferry ticket.

What follows is the practical chapter. Each entry gets its East End equivalent, because most readers of this book will not be on a boat this weekend.

Main Street, Nantucket

Cobblestones, brick, whaling money, and a shopping district that has been aggressively curated for forty years. It photographs perfectly and it knows it.

East End equivalent: Main Street in Sag Harbor. Same scale, same whaling fortune underneath, slightly more forgiving about what you wear. Southampton’s Job’s Lane is the tonier comparison, though it reads more like a shopping street and less like a town.

Bartlett’s Farm

A working farm with a market attached, seventh generation, and the single most photographed vegetable stand in New England. The show uses it as shorthand for competence and abundance, which is exactly what it is.

East End equivalent: Balsam Farms in Amagansett or Round Swamp Farm in East Hampton. Round Swamp is the closer emotional match, because the line is long and nobody complains about it.

Cru

Harborfront, oysters, rosé, and the specific social density of a restaurant where the boats are parked in your sightline. Cru is where the island performs itself at lunch.

East End equivalent: Duryea’s in Montauk for the waterfront theater, or the American Hotel in Sag Harbor for the wine list and the older money. Choose based on whether you want to be seen or want to be quiet.

‘Sconset

Siasconset, seven miles east of town, rose-covered cottages, bluff walk, and a village that operates like a private club without formally being one. It is the most photographed and least understood place on the island.

East End equivalent: Sagaponack village proper, or the residential stretch of Wainscott. Both share the essential quality, which is that nothing appears to be happening and everything is extremely expensive.

Two more places worth the walk

Brant Point Light sits at the harbor entrance and is the first thing you see arriving by boat. Tradition says you throw a penny overboard as you pass it, which guarantees your return. Nobody on that ferry is too sophisticated to do it.

The ‘Sconset Bluff Walk runs along the top of the bluff, threading between private lawns on a public right of way. It is one of the strangest and best walks in America, since you are legally entitled to stroll through some of the most expensive privacy in the Northeast.

No East End equivalent exists for that second one, and the absence is instructive. Long Island’s beach access fights have been ferocious for decades. Nantucket simply kept a footpath open and let everybody use it.

The mistake most visitors make

Day-trippers try to see the whole island. That is the error, since the island is thirty miles offshore and rewards depth rather than coverage.

Pick one village and stay in it. ‘Sconset for a full day beats town, ‘Sconset, Madaket, and Surfside crammed into six hours. The same rule applies on the East End, where trying to do Montauk and Southampton in one afternoon produces nothing but traffic.

Locals can identify a coverage tourist instantly. She is the one consulting a list.

How to do the weekend if you are actually going

Book the ferry before you book anything else, because the boat is the constraint and everything else flexes around it. Fast ferries from Hyannis run roughly an hour, while the traditional boat takes over two and is more pleasant.

Then reserve dinner immediately. In July and August a Nantucket dinner reservation is a harder asset than a hotel room, and any local will tell you so.

Finally, go in late September. The light is better, the crowd has thinned, and the island returns to the people in chapter six.