The Nantucket Chronicles

It may be the last great sandy frontier of genteel America. Dana Vachon pays a visit to old money, new money, the rich, the famous, and those who’d like to be a bit of all four.

The Way It Was

Grace Kelly was just nice, nice, nice…,” says Emma Ginley, sharing a memory of her friend with the small group sipping cocktails on the patio of her home off Cliff Road in Nantucket. “Do you know what her father did?”

It is the end of one of August’s last days and a dull gray mist rolls in from the corrugated surface of the Atlantic. One by one the assembled guests search themselves for an answer. “Wasn’t he in construction?” someone asks at last.

“No,” replies Ms. Ginley. “He was a bricklayer!”

“A bricklayer?”

“Yes! And did you know that when Grace died, she had just fallen in love with her husband? Now, isn’t that always the way it is?”

One of the most gracious hostesses to be found in any of the places where she spends her year—Nantucket, Bryn Mawr, and Round Hill in Jamaica—Ms. Ginley grows quiet at the memory of Ms. Kelly, whom she had been close with as a young woman. “Grace Kelly had the finest carriage,” she says, returning to her guests seconds later.

“Grace Kelly had the finest walk of any woman I have ever known!” concurs her husband, Dr. Tom Ginley, who has dressed for the evening in an immaculate navy-blue blazer with a green silk pocket square, his hair slicked back, a pair of emeralds linking each cuff. “There was no one like her!”

The party sits on the blue-and-white striped cushions of the Ginleys’ porch lounges, drinking Champagne and talking: Ms. Ginley recalls the time that her daughter, the shoe designer and hotelier Vanessa Noel, dated John F. Kennedy Jr. in Lyford Cay, and then Dr. Ginley shares a story about growing bored during the Korean War and sneaking behind enemy lines, just for fun. In the corner a white wicker elephant struggles under a load of freshly folded beach towels, and outside the fine green grass of the lawn rambles along a row of blue hydrangeas, toward the cliffs and the ocean beyond.

A Jamaican maid refills the crystal flutes with Veuve Clicquot and soon they are empty again. Some of the company excuse themselves for dinner elsewhere on the island, leaving with much kissing and well-wishing. Earlier Dr. Ginley had told stories about nearly crashing his miniature blue tugboat into the Nantucket ferry (“I thought it would move, but it didn’t!”) and encountering the ghost of a sailor in his bedroom (“He was a man with a lot of whiskers!”), and he now completes his channeling of Ernest Hemingway with a story about a wildcat.

“I was hunting on Pikes Peak,” he begins. “We’d been tracking a wildcat and he’d been stalking us. It went on for days. I was bleeding. Finally, at dawn, I saw him up high in a tree. I saw the wildcat. His eyes glowing at me, his shoulder blades rising, the muscles in his back gathered, and I knew he was about to spring. Well, I had no choice, I was too close to run. So I slapped off the scope of the gun and shot him then and there with my own eyes. The sensation was as great as anything I have yet known! Then I called Emma, and what she said was, ‘Are you done hunting damn cats yet? And when are you coming home?’ Imagine. A cougar confused for a damn tabby.” He shakes his head then proclaims, “Wildcat equals wildcat!”

His wife smiles at this memory, and soon it is time to move into the dining room. The sun is gone and a Sandwich-glass chandelier sparkles above the perfectly set table where a miniature wooden canoe–shaped trough is filled with oysters, mussels, clams, and lobster. The light gleams off the sapphire on Emma Ginley’s wrist and the diamond of her ring. The sapphire once belonged to an Indian noble, she explains, and the diamond had once been worn by Napoléon’s daughter. And even though Napoléon had no daughter, at least not officially, Emma Ginley is so elegant that you have to take her word on such things.

Now she rings a small bell, but nothing happens.

“You have to ring it louder, I think,” her husband says.

She does, and the same Jamaican woman appears to fill the dinner glasses with Sauvignon Blanc as the table fills with pleasant chatter. Somewhere in the house the family Jack Russell barks, and Dr. Ginley begins to share another story, this one about the day in 1957 when he, then a young doctor, and his new wife came to a quiet island 30 miles out in the Atlantic and bought an old saltbox on the water.

Here in Nantucket, among patricians with treasures and tall tales, you always find yourself feeling somehow more perfectly American. Maybe this is why, from the steam engine to the search engine, the founders of fresh fortunes have come here, the latest arrivistes forever taking their place beside the oldest aristos. Except the post-9/11 riches are vaster than any prior, and Nantucket is only so big. At some point the new can’t help but push out the old.

Nantucket is now awash in more new money than ever before. This bow of sand, bought in 1659 from Thomas Mayhew “for the sum of thirty Pounds, and also two beaver hats, one for myself, and one for my wife,” now averages about a billion dollars in real estate transactions every year. In the two months preceding my arrival last August, a record $179 million worth of property changed hands.

“The real estate here just jumped extraordinarily and people sold,” says the Ginleys’ daughter, Vanessa, when asked about the disappearance of the old families she grew up summering alongside.

The recent arrivals are spoiling this place, some say, but at this table it could truly be any moment of any day of any August in the last 60 years: Grace Kelly is here in Emma Ginley’s accent, and somewhere upstairs lurks the ghost of that old, whiskery sailor.

“We don’t go into town much now,” says Emma Ginley with a kindly smile. “We like to stay up here.”

THE WAY IT IS

I have come to Nantucket primarily to see if the worst of the complaints are true: that the latest wave of global wealth is turning the island into an American Ibiza. I need only poke my head out the door the next morning to see that this is not the case. The Gazprom executives have not arrived, nor the Saudi royals, nor the esteemed Diddy. Still, I’m waiting for Ronald Perelman to come running down the street with Ellen Barkin and her lawyers in hot pursuit. Or a Trump child. Even Tinsley Mortimer. Something. Anything. But no.

As I step outside there are even church bells tolling the doxology, the Protestant hymn of praise to God the creator. The chiming echoes down Centre Street and blows into the rooms of the Jared Coffin House. I find myself filling in the lyrics: Praise God, from Whom all blessings flow / Praise Him, all creatures here below / Praise Him above, ye heavenly host / Praise Father, Son, and Holy Ghost.

The music is soft, soothing—and fully out of sync with the bustling circus of modernity playing out all around me.

In tennis whites and with flustered nannies, they have been waiting in a line 20 deep to get inside Black-Eyed Susan’s, the famous breakfast spot on India Street. Children cry and babysitters cajole and—loathe to let a moment of vacation go to waste—a father in a Thomas Weisel Partners fleece runs a conference call from his BlackBerry, huffing down to Centre Street before stopping abruptly to avoid an oncoming SUV driven presumably by another of his kind. Nantucket never feels exactly crowded, but it always seems just a little bit more than full. And every now and again you pick up a different kind of chorus, one that might make Emma Ginley cringe, and certainly one that comes at odds with the doxology. It goes:

“I hate you!”

“Well, you’ll have a new nanny when you get back to New York.”

“No—now means now and not next week.”

“She’s up to seventy pounds.”

It is hardly difficult to see why stalwarts might eschew town, though this still might be one of the loveliest places in the world to spend a summer morning. Which is precisely why the newly rich want to be here for their precious two weeks of summer vacation: The air is crisp and the early-morning light is limpid as it reflects off windows and shines from the ancient cobblestoned streets. The shops are beautiful and their owners friendly, and even when people must dodge one another to walk down the street, they are smiling. And did I mention the tolling church bells?

The thing is, many folks here—especially those who discovered Nantucket decades ago—expect that they can play the role of that ancient beachgoer, King Knute, who famously and quixotically commanded the tides to stop crashing upon his coast.

In the most littoral sense, Nantucket’s residents have succeeded where Knute failed, recently putting together a $25 million trust to combat beach erosion and pumping 2.6 million cubic yards of dredged sand onto the island’s shrinking shores. It is the unprecedented scale and power of American prosperity that allows for such wonders, but it is this same prosperity that constitutes what is perhaps the one reshaping tide that Nantucket cannot resist.

The phenomenal expansion of American wealth in the early 21st century has changed the face of Nantucket every bit as much as the whaling boom of the early 19th century did. Americans are uniquely accepting of newfound wealth, of course; if Jay Gatsby had had children smart enough to preserve his fortune, they would be regarded as American royalty on par with the Drexels and Dukes today. And so as a new generation has acquired great wealth, it has unsurprisingly come here to spend it. Carlyle Group founder David Rubenstein, Danaher manufacturing mogul Steven Rales, and Miami Dolphins owner H. Wayne Huizenga are just a few of the self-made billionaires who have recently chosen to call this island home.

And yet the billionaires are not the ones who most affect the experience of being on Nantucket: Local retailers complain that many of them rarely leave their estates, preferring to watch movies in home theaters, swim in private pools or at remote beaches, and eat food flown in from the mainland and prepared by personal chefs. Furthermore, the self-made billionaire is a busy breed; Rubenstein is said to have bragged to friends that he spends only 12 days here every year. The truth is that the average house on the island now sells for about $2 million, not $20 million, a number that reveals an interesting aspect of the place’s transformation: It is not Nantucket’s billionaires who are most changing its atmosphere but those who travel in their wakes—the mere millionaires.

They are the ones flying in from New York on JetBlue to stay in the oceanfront suites at Steve Karp’s recently renovated White Elephant and Wauwinet inns and in the rooms at Vanessa Noel’s lovely hotel on Centre Street, where the bathrooms are luxed out with Bulgari toiletries. They are the ones on the Champagne cruise to Topper’s—the restaurant at the Wauwinet—for dinner on Saturday night, sharing stories about encounters with the great moguls of the island. They are the ones waiting in stroller-packed lines for brunch on Sundays, dreading calls from the private equity funds and law firms and investment banks that pay the bonuses that drive their lifestyles.

They make small fortunes servicing big ones, and with a staggering aggregate spending power they are reshaping Nantucket in their image. They are the ones who, in past years, have powered the success of new Nantucket institutions like the Pearl—a minimalist black-lit affair which could be a Tokyo hotel bar—and its slightly more genteel cousin, LoLa 41°, where I find myself with a coveted reservation the evening after dining with the Ginleys.

Up by the sushi bar a tall blonde in an ultrawhite tube dress glosses her lips and contemplates the yellowfin tuna. Soon she turns to greet a friend in a turquoise Pucci tube that may or may not have been a good choice to go with her gold-studded silk cheetah-print wrap. Platters of sushi are served as couples discuss what stories they will tell should they run into other couples they have been avoiding. It is a beautiful place filled with beautiful people, and it feels a lot like any other spot routinely enjoyed by the petite bourgeoisie of London, Manhattan, or Los Angeles. And if you were to be blindfolded and dropped here, then given one chance to guess your whereabouts, you would likely look around at the crowd, shrug, and offer “Meatpacking District?”

It’s not that these people want to ruin Nantucket. Rather they cannot help but change the place as they enjoy it, with every piece of sashimi eaten, every house expanded, every Lincoln Navigator ferried over. But to express horror at this is to pretend that this island was ever the Paris Commune West. Wealth has always shaped life on Nantucket as surely as the tides have shaped its shores. It’s so clear that if you don’t see it for yourself, other people will happily observe it for you.

“What are you doing?” asks a fellow diner that night at LoLa 41°, when he spots me taking notes.

“Writing an article about Nantucket,” I tell him.

“What’s your angle?” he asks.

“Maybe something postmodern?”

“Nice,” he says, then quickly, excitedly: “I think a good angle is the new rich elbowing out the old rich. You know? Like, a conflicted story?”

And just like that, he finishes out the scene.

THE WAY IT’S GOING

Luke and Carrie Thornewill could easily play themselves in a film about life on Nantucket. He is tall and tan with the weathered good looks of an America’s Cup crewman and she is L. L. Bean beautiful. The two have worked together as partners in their own architecture firm since 1995, designing homes across the island during one of the most explosive periods of expansion in its history.

Even amid a massive national real estate crisis, the growth in Nantucket’s housing market has been astounding. In 2007 the total volume of home sales reached a staggering $842 million, a 34 percent increase since 2000, and the average home went for $1.9 million—effectively doubling over those same seven years. By contrast, the number of empty lots sold this year (a measure of the island’s capacity to accommodate new growth) was only 46, a 75 percent decrease from 2000. In their work, the Thornewills have watched with unique perspective as this unprecedented development has transformed the texture and nature of life on their island.

After a five-year apprenticeship in Venice and London, where he worked with architects Leonardo and Pucci Ricci, Luke, now 46, arrived in Nantucket in 1992. It was the trough of the last great real estate bust, so in the absence of design opportunities he had come to the island on the promise of employment as a craftsman. No sooner had he taken on a carpentry job, however, than the new wave of prosperity began to roll in, bringing with it ample work for a talented young architect. Carrie, 42, joined him three years later and still remembers the early indicators that the island had been rediscovered.

“Luke would do one house in a neighborhood and all of a sudden someone else would call,” she says. “They came in pairs for six or seven years.” For a two-person shop that takes on only 15 projects a year, this was a major rush of work.

Luke and Carrie live and work far from the bustle of Nantucket town, in a home of their own design. Its rooms are filled with natural light and wood and look out through the tall reeds and waving grasses of the island’s moors. Downstairs the basement studio is filled with pictures of projects completed and the blueprints of those imagined. All of them must be approved by Nantucket’s Historic District Commission, the group widely credited with preserving the look of this old whaling town even as it becomes a posh resort.

“They’ve saved this place,” Carrie says definitively. “We may look at it now and think ‘Oh God, some of these houses have gotten out of hand and it doesn’t look like Nantucket,’ but if the HDC didn’t exist there would be much, much less of a sense of history here.”

With veto power over the stylistic aspects of Nantucket’s ongoing development, the HDC manages the look of new homes and new construction, maintaining consistency with the island’s architectural history.

But there are some things that are simply beyond anyone’s control. For the Thornewills the island’s development reached a noticeable inflection point at the beginning of the era of credit-fueled prosperity that is just now ending.

“People weren’t building their own movie theaters before 2000, when all of a sudden that became the rage,” says Luke. He then goes on to describe the same billionaire phenomenon I’d heard about from many Nantucket retailers, those whose businesses have not grown apace with the recent boom.

“There is a contingent of people here who stay within their own compounds, housing eighteen or twenty people: They can watch a movie, go swimming, do the beach, get on their boats—it’s all connected.”

And after these new billionaires came the even newer millionaires, the petite bourgeoisie arriving en masse, with requests for bionic lawns and TriBeCa floors of imported marble. These were people who viewed their second homes more as investments than heirlooms, and they’ve created a different kind of Nantucket, one that looks like a grander version of the original on the outside but turns out to be more like Manhattan on the inside.

“Everything was dramatically bigger on the island after the millennium,” says Carrie. And predictably so; aesthetics and economics are interminably joined and always have been. It is to Nantucket’s credit that design standards have been so well mandated and enforced, but in some sense this success has only made the place more attractive to the newly wealthy, perpetuating a less overt but equally significant transformation.

And so the island receives its future while reaching for its past.

“It’s a mystery as to where we’re heading,” says Carrie of Nantucket’s emerging aesthetic. “Hopefully we can retain some of the old, some of the original.”

She sits and reflects on this statement. The beautiful mêlée of town is far away. Outside it’s all afternoon sun and rambling moors. Of all the places in the world, this is the one she has chosen to live and work in and raise her family.

“The island’s gone a little glitz,” she finally says with a soft nod. “But I think it’s all still essentially there.”

Dana Vachon, author of Mergers & Acquisitions (Riverhead), wrote on Ralph Lauren in the March/April issue.

Insider Dispatch: Doing The Island In Style

GETTING THERE

Short of private jet, the most comfortable way to reach Nantucket is by Tradewind Aviation’s Nantucket Shuttle. (Delta and JetBlue, of course, also fly in.) It offers daily flights from Westchester, New York, and Teterboro, New Jersey, and private charters can pick passengers up at most Eastern Seaboard locales. Bonus: Labradors and goldens are welcome. Ticket, $595; 800-376-7922; tradewindaviation.com

Chic Stays

Killen Real Estate
Eugenie Voorhees has a discerning eye and unique access to some of the most luxurious rental homes on the island. 508-228-0976; killenrealestate.com

The Wauwinet
This beautifully restored and very private 26-room inn—with six additional cottages—is nine miles outside town. The grounds (and room 302) have sweeping bay views; its restaurant, Topper’s, is one of the best and most sophisticated on the island and a spa debuted last summer. From $700 to $1,450. At 120 Wauwinet Rd.; 508-228-0145; wauwinet.com.

The White Elephant
Pristine waterfront rooms and cottages within walking distance of town. The spa opened in August. From $600 to $1,850. At 50 Easton St.; 508-228-2500; whiteelephanthotel.com.</p>

Local Flavor

Black-Eyed Susan’s
The breakfast hot spot for coffee at the counter and a dose of the latest island chatter. Don’t miss the spicy Thai scramble or the huevos rancheros with oatmeal toast: a religious experience. Black-Eyed’s takes only 6 p.m. dinner reservations and there’s always a line, but it’s worth the wait. Breakfast, $18; dinner, $75. At 10 India St.; 508-325-0308.

The Chanticleer
Reopened under new ownership not too long ago, this French-inspired cottage in the hamlet of Siasconset has been serving brasserie fare since 1904. Its charm and fabulous food remain the same. Ask for a table on the patio. Dinner, $125. At 9 New St.; 508-257-4499; thechanticleer.net.

Galley Beach
Discerning service and outstanding food by head chef W. Scott Osif distinguish this elegant seaside bistro near Jetties Beach. Call well in advance for summer dinner reservations. Dinner, $100–$120. At 54 Jefferson Ave.; 508-228-9641.

LoLa 41°
This intimate bar and restaurant serves everything from fresh sushi to the best cheeseburger in town. It’s a favorite watering hole among those in the know. Ask for host Marco Coelho and practice your Portuguese. Dinner, $80–$100. At 15 S. Beach St.; 508-325-4001.

21 Federal
This old colonial home, a popular spot among locals, transports diners back in time. Behind the bar Johnny B is as famous for his conversation as for his delicious cocktails. Reservations recommended. Dinner, $160. At 21 Federal St.; 508-228-2121; 21federal.com.

Picnicking Preparations

Bartlett’s Farm
The place for the freshest and finest produce, meat, and flowers on the island. Picnic just down the road at Ladies Beach. 33 Bartlett Farm Rd.; 508-228-9403; bartlettsfarm.com

Provisions
This is a sandwich mecca. The Turkey Terrific is Thanksgiving between two pieces of bread. 3 Harbor Sq.; 508-228-3258

Something Natural
The heaping sandwiches on homemade breads are the draw here. Split one to save room for the buttery chocolate-chip cookies. 50 Cliff Rd.; 508-228-0504; somethingnatural.com

Retail Therapy

Mitchell’s Book Corner
You never know who you might bump into while browsing the shelves of this tiny bookstore that has an entire room dedicated to Nantucket literature. 54 Main St.; 508-228-1080; mitchellsbookcorner.com

Murray’s Toggery Shop
This family-run store is the Official Preppy Handbook in retail form. It’s a menagerie of needlepoint belts, whale pants, Nantucket Reds, and all things madras. 62 Main St.; 800-368-2134; nantucketreds.com

Nancy Chase Ivory Carvings
Scrimshander Chase and her sister, expert basket weaver Susan Chase Ottison, are the people to know for the signature women’s purse on the island—an antique basket topped with a piece of scrimshawed or carved ivory. Be prepared to place your order and then wait a few years. Seriously. These baskets are the Nantucket equivalent of the Hermès Birkin. By appointment only. At 6 Cobble Ct.; 508-228-0959.

Nantucket Looms
The best place on the island to purchase local artisanal wares: unique scrimshaw pieces, Barbara Toole’s glazed pottery, catboat oil paintings by Robert Stark, and the intricate mohair throws woven on the shop’s second-floor looms. 16 Federal St.; 508-228-1908; nantucketlooms.com

Peter Beaton Hat Studio
A custom straw-hat shop offering a host of styles from Ascot chic to floppy beach, all accompanied by beautiful interchangeable grosgrain ribbons. 16 1/2 Federal St.; 508-228-8456; peterbeaton.com

Playtime

Captain Tom Mleczko
Head out to Madaket, on the island’s west end, to fish with Tom and his son Jason. They have a nose for tracking down Nantucket’s famed bluefish and striped bass. Charters, $450–$650 per tide (about four hours). At 3 Hinckley Ln.; 508-228-4225; capttom.com.

Force 5 Watersports
This is the one-stop shop for the latest gear. Jesse can hook you up with experts in kite-surfing, windsurfing, and plain old surfing. 6 Union St.; 508-228-0700

Nantucket Historical Association’s Whaling Museum
Great for families, the recently renovated spot conjures a time when whaling captains ran one of the East Coast’s most prosperous ports. Don’t miss the view from the rooftop observation deck. 15 Broad St.; nha.org

Dionis, Quidnet, and Steps beaches
The north shore of the island offers the best beaches for families and those who want to escape for the day. These three are local favorites. nantucket.net

Sanford Farm
At the top of Main Street head west out to Madaket Road and stop about a mile down at the dusty parking lot. From there it’s a two- to three-hour round-trip walk along a historic nature trail to a deserted and breathtaking south shore beach. Nantucket Conservation Foundation, 508-228-2884; nantucketconservation.com

D. Brooke Harlow