By Chuck Strouse
By Scott Fishman
By Terrence McCoy
By Ryan Yousefi
By Ciara LaVelle, Kat Bein, Carolina Del Busto, and Liz Tracy
By Pepe Billete
By Ryan Yousefi
By Kyle Swenson
In 1956, Papy sold his island to a group called the Wisteria Corporation, which wanted to erect 60 homes, a golf course, and a yacht club. Although board members hired architectural consultants who had worked on Lincoln Center in New York, they sold it in 1967 without hammering a nail. The new owner, local land baron Benjamin Bernstein, also had the development itch; he had already built many homes, trailer parks, and commercial buildings on Stock Island, just east of Key West. In 1973, Bernstein and his family bought 150 acres of bay bottom surrounding Christmas Tree Island. But then Bernstein died in 1974, and his wife and two adult sons left the island untouched.
The first squatters probably arrived on Wisteria/Christmas Tree Island in the Sixties or early Seventies. It was a time when many young hippies headed south, and Key West became an affordable, tropical, counterculture retreat. One of them was Paul LaBombard, who hitchhiked there from Massachusetts in 1971 when he was 18 years old. He slept on a porch and then pitched a tent on Wisteria Island for a winter before drifting to India, where he changed his name, studied Buddhism, and donned a turban. Upon returning to the United States, he bought a 10-unit apartment building in Portland, Maine. By 1987, he was calling himself Pritam Singh and had amassed enough wealth with his developments to buy Key West's Truman Annex and embark on a $250 million project, which included the Key West Golf Club.
Like Singh, Jimmy Buffett arrived in Key West in the early Seventies. He came with fellow guitar picker Jerry Jeff Walker in an old Packard. It's unclear whether he stayed on Wisteria Island — Buffett refuses to give interviews to anyone these days — but he lived aboard more than one sailboat, so it's likely he cracked open a beer on its shores. He cut his third album, A White Sport Coat and a Pink Crustacean, while living in Key West in 1973. Four years later, he recorded his most famous song, "Margaritaville," which became an anthem for hard drinking and island living:
I blew out my flip-flop,
Stepped on a pop-top,
Cut my heel, had to cruise on back home.
But there's booze in the blender,
And soon it will render
That frozen concoction that helps me hang on.
Tony Beach arrived in Key West around 1987 and claims to have worked a day-labor landscaping gig at a house Buffett owned on the island. "It was a really hot day," Tony snorts. "We went to the door and asked old Jimmy for some ice water. He said the hose is over there, and pointed ... like we were dogs.
"Jimmy Buffett is a bimbo. He's nothing but a fart in an iron lung."
As a real estate boom took hold in the Eighties, people like Tony were squeezed, so they headed to Christmas Tree Island, which was then a crazy place. There were dozens of people living there, most of them in small lean-tos. Walking paths crisscrossed the tall brush, and fire pits pockmarked the beach. A woman named Delilah lived aboard a sailboat anchored offshore with her husband and two children for more than 10 years. She called the island "a back yard for boaters."
"One year we all went ashore for Thanksgiving and we barbecued a turkey," she recalls.
Mark Rossi, the owner of Durty Harry's and Rick's — two popular Duval Street bars — began hosting end-of-the-tourist-season parties on Christmas Tree in 1985. Live reggae bands played on a barge offshore, and Rossi provided food and lots of booze. "It was always an island-party theme," says Rossi.
In the early Nineties, Key West commissioners got tired of the homeless and voted to close public beaches at 11:00 p.m. But the measure backfired when a Monroe County judge rejected the measure as unconstitutional, and the decision was trumpeted around the nation as a sign of the city's insensitivity — and very non-Jimmy Buffett attitude.
Christmas Tree Island remained a freeloader haven throughout the Nineties. Through a peculiarity of mapping, it's overseen by Monroe County commissioners, not the city — so Key West city commissioners had no power to control the camp there.
By 2001, the place was happening. A girl who called herself "Road Dog" wrote an online account for digihitch.com, a vagabonding Web site. She described dinghy rides to the island from Key West. A French girl taught her to crochet and how to ask tourists for spare change. A guy named Jack had a dog that caught fish. A Cuban rafter who squatted there erected a "two-story teepee" and invited her for potluck dinners. Grateful Dead fans built a "jungle-gym trail through the trees," Road Dog recalled. "Australian pines are easy to climb, and when you get near the top of one, you can sway to the next tree like a monkey! It's great!"
Adds Dale Pritchard, a sword swallower by trade and onetime Christmas Tree live-aboard: "It was crazy out there. I once saw a guy onshore shoot at a guy in a dinghy with a .22 pistol. Then the guy in the dinghy fired a flare gun into the other guy's boat, and the boat caught on fire."