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He’s Mr. Key West — and owner of his own private island

By Amy Driscoll

David Wolkowsky sits inside his open-spaced home filled with his personal artwork and vegetation in Key West, Florida,  on land that he inherited from a dear friend.
David Wolkowsky sits inside his open-spaced home filled with his personal artwork and vegetation in Key West, Florida, on land that he inherited from a dear friend. MCT/Miami Herald

The land wasn’t much to look at 50 years ago, a beat-up bit of coastline in a run-down island town, not even a beach to recommend it. But David Wolkowsky, the urbane, Panama-hatted visionary of modern-day Key West, took one look and thought: chic hotel.

It was vintage Wolkowsky. A burst of inspiration greeted by a lot of head-shaking followed by against-the-odds success. The 1968 opening of his Pier House hotel, with its air of “elegant inefficiency,” as writer and friend Truman Capote put it, is now widely considered the turning point in Key West’s transformation from washed-up military outpost to funky tourist destination.

And it was a defining moment for Wolkowsky. For the next five decades, he would put his unconventional stamp on the island where he was born. Not so much the honky-tonk tourist side, though that was part of it, but the other Key West, the place where front porches serve as art installations, bike bells replace car horns and night-blooming flowers perfume the air with mystery.

“When I look at things, I’m always desperately looking for beauty,” says Wolkowsky, who will turn 93 this month. “But I don’t like the word beauty — do you? I’m looking for something a little offbeat.”

Even in a town that prides itself on local eccentrics, Wolkowsky is legendary. A millionaire who used to drive the streets in a vintage Rolls Royce or a golf cart, he pals around with famous writers and artists, salvages historic buildings and owns the only private island south of Key West, where he built an architectural marvel of a house. Yet he has managed to remain surprisingly low-profile outside the oddball island that once declared itself the Conch Republic and tried to secede from the U.S.

“He’s very quiet about it, but he’s Mr. Key West. He really is,’’ says best-selling author Judy Blume, of Are You There God? It’s Me, Margaret fame. She and her husband bought a house in Key West in large part because of Wolkowsky.

“He took us in and we never wanted to leave… There’s nobody else like David. It’s his love of life, his joie de vivre, his enthusiasm. It’s his humor, his sly humor. And sure, it’s his history. Who wouldn’t be enthralled by his history?”

When man and island are a match

In Wolkowsky’s world, there is really just one rule: Make it interesting. “It’s like a little bomb that excites me that kind of explodes in my mind,” he says. “It’s an excitement. I’m always looking for the exciting view… I’m always looking for something that has a sense of originality.”

In that sense, man and island couldn’t have been better matched. Wolkowsky has found enough offbeat beauty in Key West’s less than six square miles to keep him interested for five decades.

That’s especially true of the weathered buildings that he has restored, renovated and sometimes relocated, a list so long he has lost count. But a few stand out: Ernest Hemingway’s original watering hole, Capt. Tony’s Saloon, a landmark structure Wolkowsky and his sisters inherited from their father. The Kress building, an old dime store now home to both Jimmy Buffett’s Margaritaville Cafe and a rooftop penthouse Wolkowsky built for himself. The two dozen U.S. Navy surplus buildings he moved by flatbed truck and transformed into shops near the Mallory Square docks.

Today’s Key West, which has retained a lot of its village charm despite incursions by chain stores and cruise ship daytrippers, is in many ways a David Wolkowsky production.

“We often say whatever you like about Key West can be put on his doorstep because that’s really true,” said Claude Reams, who has known Wolkowsky since 1977 when Reams and partner Joe Alan Carr opened the Assortment men’s store in the Pier House. “We don’t think David gets his due.”

Wolkowsky was both builder and preservationist back when Florida had little sense of its own history, notes Miami historian Paul George: “He was into preservation before preservation was cool.”

And then there’s his other island.

He bought Ballast Key in the mid ’70s, a scrubby rock outcropping in the Key West National Wildlife Refuge, and hatched a crazy-sounding plan to build his masterpiece, a lighthouse-inspired structure that became the southernmost private home in the United States. It required a barge, a desalinization plant and years of tenacity but these days an invite on the eight-mile boat ride out to “David’s island” is proof you’ve made it by Key West standards.

And what a guest list it has been, at both island and hotel. Because Wolkowsky’s fascination with the physical landscape is equaled by his love of the arts, he has hosted luminaries like Leonard Bernstein, Rudolf Nureyev and Lillian Hellman. Tennessee Williams was a frequent guest at Ballast Key, where he tried his hand at painting, including a haunting portrait of Wolkowsky, inscribed with the words: “It’s the eyes.” And Capote, the famously erratic writer of In Cold Blood, stayed in a Key West trailer owned by Wolkowsky and gave his host a manuscript during a middle-of-the-night departure that, decades later, would spark a bit of a literary mystery.

Every January, during the Key West Literary Seminar, Wolkowsky — who bought Greta Garbo’s letters after she died, even though he met her just once — throws a cocktail party for the authors in his book- and art-stuffed penthouse. Guests might include seven poet laureates — and the bartender from around the corner.

After this year’s event, William Gibson, author of Neuromancer and originator of the term “cyberspace,” tweeted: “Met the amazing David Wolkowsky at his drinks party last night. Hosted in dreamlike interstitial town house atop a onetime Kress dime store.”

Key West to Miami to Philly and back

Though Wolkowsky was born in Key West, where his grandfather opened a store in the 1880s, the family moved to Miami when he was a child. His sister, musician Ruth Greenfield, eventually founded what is believed to be the first interracial arts academy in Florida. But Wolkowsky’s creativity was focused on design. After attending the University of Pennsylvania, he made a name and a fortune for himself in Philadelphia, restoring buildings, until his father died and he returned to Key West in 1962. A plan to retire at 42 lasted barely a year: He bought the land for the Pier House and never looked back.

But there is one thing from the past that nags at him. About 15 years ago, the original manuscript Capote gave him during that abrupt nighttime departure disappeared from his penthouse — and the only suspects were friends who had stayed in the apartment at his invitation.

It’s a mystery with a Conch gothic touch that he’s never publicly discussed before, but now he wants to make sure there’s a record and that no one tried to sell the documents after he’s gone. “I just want it known that this is something that was given to me by a friend,” Wolkowsky says.

The missing manuscript has an intriguing history of its own. It’s believed to be an early draft of La Cote Basque, a scandalous exposé of New York society published in Esquire in 1975 that some say caused the suicide of a socialite who appeared, thinly veiled, in the piece. Ann Woodward was acquitted of murdering her husband but Capote’s short story, featuring a fictionalized account of the killing, essentially convicted her.

Wolkowsky kept the original in a plastic grocery bag tucked into a filing cabinet in his penthouse, making one copy so he could frame some pages. But after several sets of friends had stayed in the apartment, he realized the bag and its contents were missing. No one confessed, so he says he placed a “blind” item in a local paper about the disappearance, keeping his name out of it, and circulated copies among his friends. Still, nothing.

It’s the violation of a friendship that still rankles.

“If he believes in you, you get his unwavering loyalty and support,” says Tom Schmitt, former owner of the Rooftop Cafe, who says he was able to open the second-story eatery only with Wolkowsky’s help. “With his eye and his way of looking at things, he can see the potential in something — and in people — that somebody else can’t.”

His personal style is a mischievous mix of high and low. In the penthouse — he owns several properties on the island, though he sold the Pier House in the late ’70s — an expensive Art Deco-style Aubusson rug resides on a floor that, on close inspection, turns out to be made of polished plywood. On Ballast Key, he is famous for serving guests turkey hot dogs and chips while they gaze at the one-of-a-kind view. When he ran the Pier House, back in the ’70s, federal drug agents might be sitting at one end of the bar and smugglers at the other.

He collects art the same way, notes Claudia Pennington, executive director of the Key West Art & Historical Society, who says he’s been known to return from a trip with a shipping container of items he can’t wait to show her. “It’s everything from, ‘look at what I bought in Paris’ to ‘I saw this in the gutter at Stock Island and it was too good to throw away.’ And for the most part he’s right on,” she says.

When asked to talk about his accomplishments, he shies away. Eventually, though, he produces a stack of magazines with stories written about him over the years — “in a burst of modesty” he notes, with a barking laugh at himself — that include a glamorous Italian men’s magazine photo shoot.

His enthusiasm, for the island and for the creative life, seems undiminished by time, notes longtime friend and literary critic Phyllis Rose, who has produced a photo book celebrating Ballast Key. “The persistence of his creative urge, at the age that he’s at, that he keeps undertaking projects —it’s remarkable.”

An array of famous, talented friends

He has famous friends — a young Jimmy Buffett sang at the Pier House bar, future Florida celebrity chef Norman Van Aken worked the breakfast service at the hotel restaurant, actress Tilda Swinton is rumored to have visited Ballast Key this year — but he dislikes name-dropping. When asked who he has invited to his island, he answers in typical cryptic fashion. “The works. Everything from garbage collectors…” he pauses, then delivers the jab, “down to Vanderbilts.”

He has a practical side, too. Local artist Susan Rodgers says he likes to get to art shows early to buy something, a psychological prod for others. “Then there would be a little red dot by some of my pieces,” she said, “and it would help create this buzz.”

Van Aken, who is writing a memoir about his life as a chef — including a chapter on the Pier House — notes that Wolkowsky, “had a quiet way of managing. He never met with all of us, just walked through the kitchen and said something like, ‘I think you ought to do Key Lime pie.’ ”

John Martini, a Key West artist who notes that he learned much about the art of negotiation from Wolkowsky — sometimes to his own disadvantage — says Wolkowsky knows just how to draw people in: “When he’s struck by someone he thinks will be an asset to the town, he seduces them — in a no-sex way. He makes people feel special and they see the island through his eyes, loving it like he does.”

On a spring day, Wolkowsky is riding shotgun in a small boat bouncing through the choppy waters on the way to Ballast Key. Conversation slows and then stops as Key West recedes and his island, some 24 acres of personal creation, appears on the horizon. The house is gray, suspended above the sand on steel, stilt-like supports, with a tiny widow’s walk on top. A dock stretches out into shallow, crystalline waters. He walks the length of it slowly — a slight concession to age — but then climbs onto the small John Deere all-terrain vehicle awaiting him. As the boat captain and caretaker tote supplies to the house, he cranks up the vehicle and tours his sanctuary, puttering past silvery palm trees and thick mangroves, each turn leading to a new oasis: a thatched hut overlooking the water, a carved bench, a piece of sculpture.

Inside the house, where sunlight drenches pale rooms, he points out a new piece of art next to the metal spiral staircase that leads to the upper bedroom, with its 360-degree water view. In the bathroom, there’s a signed Buffett album on one wall (“Ballast Key was neat for me,” it says) and side-by-side framed pages from Town & Country magazine, 1955, showing the “man of the month.” Wolkowsky is March; Cary Grant follows, in April. He adjusts a sliding glass door to catch the breeze and scans the horizon. There is a beautiful emptiness out there: no people, no boats, nothing but pale blue sky blending into turquoise sea studded by black specks of mangroves.

“I couldn’t bear to sit around and collect baseball cards,” he says. “If you’re not involved and enjoying what’s around you, you might as well get back in the book, like a leaf, and close it.” And he throws back his head and laughs.