David Wolkowsky, a visionary developer and preservationist who helped transform Key West, Fla., from a roistering former Navy town into a bohemian haven and a tourist destination, died there on Sunday. He was 99.
His death, at Lower Keys Medical Center in Key West, was confirmed by the photographer Timothy Greenfield-Sanders, a nephew.
Mr. Wolkowsky was known locally as “Mr. Key West” for his role as a catalyst in the island’s revival. In recasting it as not only a vacation haven but also an artists’ colony, he befriended literary figures like Ernest Hemingway, Gore Vidal and Judy Blume and rented his bamboo-topped two-bedroom trailer to Truman Capote, who wrote his unfinished final novel, “Unanswered Prayers,” there.
Jimmy Buffett got some of his first gigs playing for drinks in the Chart Room bar at Mr. Wolkowsky’s waterfront Pier House hotel, where he also featured the reggae star Bob Marley.
By 1993, Islands magazine credited Mr. Wolkowsky, a native of the island, with “almost single-handedly converting Key West into America’s most distinctive tropical resort.”
He bought and restored the island’s original cigar factory and the Cuban ferry docks next to Mallory Square; helped rescue Captain Tony’s and Sloppy Joe’s, saloons of Hemingway fame; revitalized the old shops along Pirate’s Alley; and transformed the steamship office into Tony’s Fish Market.
Mr. Wolkowsky’s goal was to “preserve the past by making it work for the present at a profit,” he told The Miami Herald in 1969.
He hired the architect Yiannis B. Antoniadis to design waterfront accommodations around Tony’s restaurant, which he named the Pier House in 1968 and which Renee d’Harnoncourt, a former director of the Museum of Modern Art, described as the “most unusual motel design in America.”
In 1974, Mr. Wolkowsky bought Ballast Key, an uninhabited 24-acre outcropping eight miles off Key West, for $160,000 and there built the southernmost private home in the contiguous (more or less) United States.
In August, the Monroe County Commission voted to rename the island David Wolkowsky Key after he died.
David William Wolkowsky was born on Aug. 25, 1919, a grandson of Jewish immigrants from Russia who had moved from New York to Jacksonville, Fla., and then to Key West, the southernmost Florida key, in the late 1880s. There they opened a men’s clothing store on bustling Duval Street.
His father, Isaac, ran the family store. His mother, Freda (Yubas) Wolkowsky, was a homemaker. When David was 4 and the local economy was failing, the family moved to Miami, where he grew up.
His closest immediate survivor is his sister, Ruth Greenfield.
Mr. Wolkowsky was on a pre-med track at the University of Pennsylvania in Philadelphia when he became interested in architecture and decided against medicine as a career.
“I wasn’t cut out to be a doctor; I was cut out to see a doctor,” he told Michael Adno in an article, “This Man Is an Island,” published this year in The Bitter Southerner, a digital newsletter.
After graduating in 1943, Mr. Wolkowsky served in the merchant marine; moved to New York, where he had a $25-a-week job as a floor walker at the Lord & Taylor department store (“I wasn’t very good at my job,” he recalled); and then returned to Philadelphia. There he began a modest restoration business under the name of David Williams. His projects near Society Hill and Rittenhouse Square in Center City won accolades from Town & Country magazine in 1955.
After inheriting property in Key West’s Old Town when his father died in 1962, Mr. Wolkowsky harbored visions of a life of leisure. But he was only in his 40s and failed miserably at retirement.
“I couldn’t bear to sit around and collect baseball cards,” he told The Herald in 2012. “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.”
Where others saw an economically depressed and hurricane-ravaged six-square-mile island with subpar beaches strung with barbed wire to guard against invading Communists from Cuba, Mr. Wolkowsky envisioned something entirely different: the renaissance of a community.
The keys to unlocking its potential were its tropical weather, Hemingway mystique, charming architecture and kooky locals, who assembled daily at dusk to salute the sunset.
Mr. Wolkowsky would tool around town in one of his flashy cars, including a cream-colored Excalibur; serve guests turkey hot dogs and chips; and practice the adage that giving is better than receiving. (At his birthday party in August, he presented several dozen women with black pearl necklaces.)
“I was lucky to have an uncle with a world-class wit, a private island and a 1926 Rolls-Royce, on which I learned to drive,” his nephew Mr. Greenfield-Sanders said by email. “The other side of him gave annually to local teachers and was the greatest visionary that Key West will ever know.”
For a time Mr. Wolkowsky lived atop the old Kress Building on Duval Street, above the Margaritaville cafe, where he said he felt safer than he ever had because he had rented the upper floors to the Key West Parole Board. Nonetheless, someone stole a prized possession: handwritten drafts of “Unfinished Prayers” that Capote had rejected and given to him in lieu of rent.
Another keepsake survived: his portrait, drawn by the playwright Tennessee Williams, who had moved to Key West. Scrawled across it, in French, is an inscription suggesting Mr. Wolkowsky’s standing as a visionary. Williams wrote, “The unknown: It’s the eyes.”