The island's New England traditionalism, studied unpretentiousness, and astounding wealth have made it one of America’s most iconic warm-weather destinations. But Nantucket is also a state of mind—one in which big ideas are the most powerful currency of all.

Nantucket Summer
Nantucket’s characteristic gray-shingled estates, as seen from an upstairs room at the Wauwinet.
| Credit: Roland Bello

"I think Nantucket is a romantic notion,” said Kate Brosnan, who has lived on the little island south of Cape Cod, Massachusetts, for 37 years. We were sitting at the White Elephant, a waterfront resort hotel where each September Brosnan helps assemble a new edition of a think-y, TED-style conference called the Nantucket Project. A Wall Street refugee, she arrived in Nantucket in the winter of 1979 and never left. “I thought I had found the perfect little sleepy place,” she said. And then, of course, summer came—and with it, the hordes.

Brosnan was, and still is, okay with the tourists, though lately high-season traffic has been heavier than ever. “Nantucket definitely goes through cycles, but right now it’s more popular than I can remember,” she told me. In the summer, the island’s population swells from around 10,000 to nearly 60,000. Many are drawn by an idea of the place that Brosnan has helped nurture as executive director of the Nantucket Project, which was founded in 2010 by Tom Scott, the entrepreneur who made his fortune with Nantucket Nectars. “Nantucket,” as Brosnan put it, “has a rich history of forward thinking.”

Think of Nantucket as a kind of nation-state unto itself, whose residents have a long, proud tradition of seeing themselves as extraordinary. Many locals, Brosnan said, refer to returning to the mainland as “going back to America.” I visited at the end of the season, when the Nantucket Project takes place. On the grounds of the White Elephant, next to a row of piers on the harbor, some 400 grandees from the island and around the world gathered for four days in a simple white tent, usually used for weddings, to sit in folding chairs and listen to brilliant people speak. The presenters, mostly boomer-aged, were a curious mix of the ruling class (Tony Blair, Lawrence Summers) and the counterculture (Stewart Brand, Neil Young).Left: Murray’s Toggery Shop, Nantucket’s most venerable preppy retailer, has been in business for 71 years. Right: The view of Nantucket Harbor from the Wauwinet hotel, a luxury property on the northern tip of the island. Roland Bello

The event lets Nantucket quietly signal its enduring economic, political, and cultural power, thanks to the elite who have second homes on the island. Secretary of State John Kerry and philanthropist Teresa Heinz Kerry have a house here. So do Eric Schmidt, executive chairman of Alphabet, Google’s holding company, and his wife, Wendy, who are also active in cultivating the intellectual life of the island. Nantucket is, yes, an idyllic setting. But it’s an idyllic setting for important people with important ideas.

It’s been like this since before Nantucket became Nantucket. A 10-minute walk from the White Elephant is the Nantucket Atheneum, the island’s public library, where Ralph Waldo Emerson, Henry David Thoreau, Horace Greeley, and Lucretia Mott all spoke in their day. In 1841, Frederick Douglass addressed a white audience for the first time in the original Atheneum, which was destroyed in the Great Fire of 1846, an event that still looms large in the life of the village. The stately Greek Revival building that stands today is a hasty reconstruction of the earlier structure.

I stayed a few blocks away at the 171-year-old Jared Coffin House. My elegantly decorated room—floral wallpaper, Queen Anne chairs, an Oriental rug over a creaky floor—felt pleasantly trapped in time. I wondered who else might have slept in it. Later, I learned that Herman Melville had been a guest in 1852, when he visited the island that helped inspire Moby-Dick, though the hotel makes no effort to publicize this fact. Nantucket wears its history without pretension. Visitors to Cisco’s expansive patio are frequently treated to live music. Roland Bello

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Much of the community’s upper class converted to Quakerism in the 18th century. On a humid Saturday, I stopped by the still-active Quaker Meeting House, a squat, gray, wooden structure that sits five minutes south of the Atheneum. Inside, among the severe oak pews, it was pin-drop quiet and miraculously 10 degrees cooler.

The tension between Quaker modesty and material wealth is woven through Nantucket’s history. Continuing my tour of the island’s center, I came to an unassuming structure on Main Street marked with a plaque that reads, “In this building, R. H. Macy, home from the sea, is said to have embarked upon his merchandising career.” After working on a whaling ship, Rowland Hussey Macy, a local Quaker, sold dry goods here. He later made his way to New York and launched a retail empire. (Macy’s red-star logo is based on a tattoo he got on a trip to East Asia.) The building now houses Murray’s Toggery Shop, a purveyor, since 1945, of clothing for ladies and men, including blazers, pants, and shorts in the dusty rose shade known as Nantucket red.

Farther along Main Street, I grabbed a late lunch at the soda fountain at Nantucket Pharmacy, which has been around since the Depression. I had a grilled cheese sandwich and coffee in a paper cup while poring over a copy of the Inquirer and Mirror—“Nantucket’s Newspaper Since 1821.” Nantucket Pharmacy used to have a friendly competitor next door, Congdon’s Pharmacy, which had its own lunch counter. When it shut down in 2007 after 147 years in business, the Inquirer and Mirror pronounced it “the end of a Norman Rockwell era.”

Many of the locals who still mourn Congdon’s also remain agitated about the Ralph Lauren store that opened in 2005 just across the cobblestones. While it hardly stands out—the exterior of the historic two-story building, purchased for an eye-popping $6.5 million, was sensitively restored—its arrival mobilized Nantucketers to resist further encroachment from mainland retailers by voting to ban chain stores. So, by law, you won’t find a Starbucks downtown or anywhere else on the island.Left: A staffer in the wine bar at Cisco Brewers, which rolls a brewery, winery, and distillery into a single venue. Right: Islanders come to Murray’s Toggery to stock up on duds in the distinctive color known as Nantucket red. Roland Bello

Beyond the chain-store ban, the preservation of the soul of Nantucket is manifest in other legal restrictions, like Chapter 139, Article IV of the building code, which limits the height of all new construction to 32 feet. Last year, Nantucket also voted to prohibit the sale of helium balloons. It was ostensibly an environmental measure, but one wonders if the gaudy presence of balloons outside otherwise tasteful souvenir shops might have had anything to do with it.

Steps from Nantucket Pharmacy was a miniature greenmarket in the back of a pickup operated by Bartlett’s Farm, the oldest on the island. Locals and visitors milled about, loading up on tomatoes, squash, and cut flowers. I ran into Christy Tanner, a CBS News executive I know from New York, on the sidewalk. She was in town to speak at the Nantucket Project, but had arrived early to take in the sights on a rented bicycle. Together we marveled at the historically correct, prim-and-proper residential architecture beyond Main Street—a sea of weathered gray-shingled cottage-style homes. “I can’t tell if this is the most liberal conservative community or the most conservative liberal community I’ve ever been to,” she said, laughing.

The truth is, Nantucket has always been a curious mixture of establishment and anti-establishment. A couple of blocks from the Nantucket Pharmacy stands a two-story brick building that dates to 1772. A historical marker notes that, beginning in 1854, it was the home of the Pacific Club, a hangout for the “captains of the whaling fleet of the Pacific Ocean.” Before that, it had served as the counting house (i.e., the accounting headquarters) of William Rotch, owner of the Dartmouth, the Beaver, and the Eleanor—the three ships involved in the Boston Tea Party in 1773. Rotch and his fellow shipowners had a lot of cash to tally and good reason to rebel against the Crown’s policies on taxation. The great seafaring vessels that docked in Nantucket Harbor were invariably involved in whaling, the spectacularly treacherous—and for shipowners, spectacularly lucrative—trade that financed the island’s early history. The excellent Whaling Museum on Broad Street, near the ferry terminal, documents their exploits.

But when whaling collapsed in Nantucket in the mid 1850s—in part because the shallow waters off its shores couldn’t accommodate the industry’s increasingly massive ships—the community pivoted to tourism. As with neighboring Martha’s Vineyard, “summering” on Nantucket became a big deal. A 1937 Life magazine feature described the islands as “summer resorts where natives have not completely sold their souls or their independence to the tourist.”Left: Incoming ferries pass Brant Point Lighthouse, a century-old wooden tower that is still used today. Right:Harissa-spiced littleneck clams at Station 21, a New American restaurant that opened last summer in downtown Nantucket. Roland Bello

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Nantucketers might argue that they’ve done a better job at not selling out than their neighbors to the west. In peak season, the Vineyard’s population balloons to more than 100,000. For a portion of the summer, however, tiny Nantucket Memorial Airport—clad in weathered gray shingles, of course—is the second busiest airport in New England, after Boston’s Logan. That’s thanks in part to JetBlue, which has added numerous direct flights from JFK and other major East Coast airports over the past decade. But it’s also because of all the private jets bringing in the superrich.

The presence of these one-percenters helps Kate Brosnan and Tom Scott immensely in programming the Nantucket Project. The organization’s “founding circle” includes former Barclays CEO Bob Diamond and his wife, Jennifer, as well as Wendy Schmidt. JetBlue, BMW, and U.S. Trust, the private wealth-management division of Bank of America, are among the corporate sponsors. Many of the island’s summering elite make a point of sticking around (or returning) for the Nantucket Project in September. The rest of the crowd consists mainly of semiprofessional thought-conference-goers who live for the thrill of low-key networking with powerful people who let their guard down in Nantucket.

Because, despite all the wealth, Nantucket pretty much forces you to let your guard down. Discussions at the Nantucket Project took place with an absolute minimum of pomp and circumstance. One day I found myself a few yards from Tony Blair, who was having his picture taken by a barefoot photographer. His security detail was invisible to me. Later, Steve Wozniak passed me before going onstage to debunk as “just a myth” the idea that he and Steve Jobs started Apple in a garage.Left: Merchandise at Spyder Wright Surfboards, in the island’s historic downtown. Right: The immaculate lawn of the Wauwinet hotel, an inn built in 1875. Roland Bello

One afternoon at the White Elephant, I got to talking with Barry Sternlicht, a travel industry legend who founded W Hotels and Starwood Hotels & Resorts. He and his wife, Mimi, bought a summer house here in 2004. “Nantucket is my oasis,” he told me. “It’s where I go to be calm. There’s none of the pressure of the Hamptons—like, who’s having the best party? You’re not showing off. It’s a very New England vibe. If you’re a woman, you don’t have to put on makeup before you go out.”

This is partly because there is, by design, not that much to do. However, you can credit Sternlicht with bringing a bit more nightlife to Nantucket. He was instrumental in the 2007 renovation and reopening of the Dreamland Theater, which incorporates a portion of a building that, naturally, first served as a Quaker meeting house. The Sternlichts teamed up with the Schmidts and several other stalwart Nantucket couples on the project because, as Barry Sternlicht explained, “we didn’t want to take a ferry just to see a movie.” In addition to first-run films and special screenings, the theater hosts live HD broadcasts from the New York Metropolitan Opera and the Bolshoi Ballet, concerts, dance recitals, and other events. It is also used by the Nantucket Film Festival, another of the island’s important summer gatherings of influencers.

I took in a mediocre Johnny Depp flick there one night. As I waited to enter the theater, I heard several moviegoers greet the teenage ticket-taker by name. Afterward, I walked to one of the hottest restaurants in town, the Nautilus, where I scored a seat at the bar. Liam Mackey, the chef, is known for inventive Asian-Spanish-Latin dishes. My waiter brought me a series of marvels on small plates: first, a salad of kale, wheat berries, roasted squash, pickled corn, kohlrabi, blue cheese, and shiitake-soy vinaigrette; next, barbecue pork riblets marinated in lemongrass with a chili-black-bean sauce. While listening to the bartender dish mixology gossip with patrons, I drank two Golden Goose cocktails (citrus vodka, grilled pineapple, and togarashi). The atmosphere at Nautilus was low-key, like the rest of downtown Nantucket. But the upscale, high-concept fare would not have felt out of place in the Hamptons.

“There are no Maseratis in the driveways here,” Sternlicht had told me at the White Elephant. “The national bird here is the Jeep.” His point was that on Nantucket there is little tolerance for ostentation. There is, however, considerable tolerance for astronomical housing prices. The median home value on the island is more than $1.2 million, the highest in the state of Massachusetts. While there, I saw a five-bedroom, 4½-bath harborfront estate on three-quarters of an acre listed for $29.6 million.

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On my last day in Nantucket, I headed to its eastern edge to truly get away from it all. I walked for miles along the area’s streets and beaches, particularly in and around Siasconset (a.k.a. ’Sconset), a town of about 200. By mid-afternoon, everyone else had disappeared and I had an entire stretch of the beach to myself.

I began to have an eerie, last-man-on-earth feeling as I headed north on the ’Sconset Bluff Walk (a.k.a. ’Sconset Foot Path) toward the Sankaty Lighthouse. Even in peak season, the path stays quiet—partly because it is hard to find and partly because its final stretch has been closed thanks to erosion, which has destabilized the bluff.

The path is a thin strip of land that was deeded to the people of Nantucket in 1892 by developer William F. Flagg. A small sign marking the start of the walkway—which is little more than dirt and trampled grass—includes the full text of a poem by Abbie Ransom. It begins,

Have you ever followed the path along the bluff
When the sky is gray and the sea is rough?

And ends,

To the west the moorlands, above the sky,
In all the vast silence, just God and I

Rather bizarrely, the path cuts through the front yards of many beautiful houses. I spotted signs warning against using the rickety old wooden staircases, built into the bluff, that lead to the ocean. One read, Danger: Path Closed D e To Erosion—the U in due having been washed away. According to the Siasconset Beach Preservation Fund, certain stretches of the bluff have been disappearing at a rate of four to five feet per year.

The Sankaty Head Light Station, as the Coast Guard calls it, first shone its light, powered by whale oil, in 1850. Electrified in 1933 and automated in 1965, it is in operation to this day. Because the northern portion of
the ’Sconset Bluff Walk is closed, to reach the lighthouse I had to detour along Baxter Road, a residential street that is itself, in places, perilously close to the eroding bluff.

With the low roar of the ocean as a soundtrack, I thought of the existential subtext—the ceaseless waves doing their damnedest to reclaim Nantucket—and the strange fact that this exclusive playground for the
rich will only get more and more exclusive, given that there’s less and less real estate to covet with each passing year. Nantucket is quite literally shrinking. In fact, if Sankaty Lighthouse had remained where it was built, it might have been swallowed by the Atlantic by now. A 2007 preservation project lifted the structure off its foundation and trucked it 405 feet northwest of its original location.

As dusk fell, I reached the end of Baxter Road and arrived at the iconic red-and-white lighthouse by a dirt path that leads to its stark black door. I was the only visitor, and though I knew it no longer had a full-time keeper, I couldn’t help knocking.

I listened too long for stirring within, but there was none. That evening, it really was just God and I.

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The Details: What to Do in Nantucket, Massachusettes


Jared Coffin House: A pair of stately, three-story, red-brick mansions with simple, elegant rooms. Doubles from $395;

Veranda House: A Nantucket landmark, this wood-shingled hotel has picture-perfect harbor views from its wraparound balconies. Doubles from $409;

The Wauwinet: Guests in the stand-alone cottages and the beautifully decorated rooms in the main inn have access to two private beaches. Doubles from $825;

White Elephant: This iconic harborside hotel is within walking distance to downtown attractions and provides pampering at its Nantucket Spa. Doubles from $825;

Restaurants & Bars

Black-Eyed Susan’s: This diner-style restaurant is best known for its breakfast, but dinner dishes like Macanese coconut chicken curry and seared beef with poached shrimp are unexpectedly good. Entrées $16–$28;

Brant Point Grill: The restaurant at the White Elephant serves hearty fare, including a 16-ounce prime aged rib eye and a twopound New England lobster. Entrées $26–$64;

Cisco Brewers: Go for drinks and live music on the patio at Nantucket’s popular distillery, winery, and brewery.

The Nautilus: A downtown destination for dishes inspired by Asia, Spain, and Latin America. Small plates $9–$24;

Station 21: This New American restaurant serves sophisticated comfort food like pizza topped with prosciutto and farm-fresh eggs. Entrées $21–$36.

Topper’s: The formal dining room and casual patio at Wauwinet showcase regional ingredients including Retsyo oysters harvested just 300 yards away.Prix fixe $80;

Special Events

Nantucket Film Festival: The annual event—June 22–27 this year—focuses on screenwriting and draws visitors from around the world.

The Nantucket Project: This year the thought conference, held on the grounds of the White Elephant, runs September 22–25.