IN SEARCH OF FLORIDA COOL
KEY WEST OFFERS A BOHEMIAN VIBE FOR CHILLING OUT WHILE STAYING WARM
Ayoung woman sits quietly in her fold- out chair, clutching a typewriter as throngs of tourists assemble outside The Ernest Hemingway Home & Museum. A small handwritten sign reads “Poet for Hire.” For a donation she cranks out poems on the spot on rough scrap paper. I get one. Four quatrain stanzas on the spirit of travel. It’s wonderful, and the experience doesn’t feel contrived. Later, she’ll have to share the sidewalk with tchotchke vendors, but for now, this enterprising artist is capturing the Key West vibe.
That spirit — one of escape, expression, and generally finding a chilled out lifestyle with a small community of like- minded people thrives through tourism, not despite it.
Frankly, I expected the façadism. I expected holiday compounds (these do exists, but tucked — rightly — away) and trendy, but ever- underwhelming chain dining. Instead I found myself in a place that’s fiercely opposed to the dilution of its artsy- hippie vibe. Key West’s population is peppered with escapees — artists or musicians looking for warmer spots to strum.
It’s an appealing escape — the Florida Keys are made up of hundreds of islands ( depending on which landmasses you include, the archipelago chain has anywhere from 800 to 1,600 islands) and a population of only around 80,000 people. I can see myself finding a shack, hooking up some decent Wi- Fi and not going back to another wind-chill warning.
Key West gets the most attention because it’s the biggest and most developed island. A full third of the Keys’ population lives here, and as the furthest Key from the mainland, that tally rises and falls drastically as monstrous cruise liners pop in for visits.
Those big ships bring in the tourism money these days, but back in Key West’s early days, you had to make sure a ship crashed before you could cash i n. Shipwrecking was big business.
The Hemingway Home and Museum offers a comprehensive run- through of the region’s wrecking roots — where fortunes were made salvaging booty from shipwrecks (and selling it back at a premium). A tour there does double duty on local history and literary history — first exploring the life of Asa Tift, an architect-turned-wrecker who built the house, then Hemingway, who lived there through the 1930s. Those were some of his most fruit- ful years, but besides leaving lasting literature, he left his cats — the grounds are home to dozens of mostly polydactyl (six-toed) cats descended from Hemingway’s own.
While the general Key West vibe is non- conformist, it’s not without its overtly tourist elements in the form of cheesy pun T-shirt shops and manufactured-fun joints like Jimmy Buffett’s Margaritaville (yes, he did write the song — at least partly — in Key West) or Sloppy Joe’s, popularized by notable drinker Hemingway.
Sloppy Joe’s started out down the street, at a bar now called Captain Tony’s. This is where Hemingway kicked back in the 1930s, and it’s worth seeking out. Buffett hung here, too, jamming out on the tiny stage in the 1970s. In fact, there was plenty of hanging here over the years — a tree found right in the middle of the place was used to execute more than a dozen pirates in the 1800s before the building became a morgue, then bordello, then bar.
Escape, by now, is clearly something people do, or try to do, here. Back in the 1980s, the whole motley collection of Keys decided to escape from the United States.
It was a simpler time — the 1980s — and America was busy waging a war on drugs. That meant setting up border checkpoints inside the U. S. The thinking was they’d be able to catch more drug runners making the run north from the Keys to Miami, but it turned out they caught a lot of tourist bycatch, too.
I’ve had the pleasure of being stopped at one of these militarized checkpoints on a deserted highway in Arizona a few years ago, and the idea of having a rougher shakedown than at an actual international border is a bit of a holiday buzzkill.
The Keys fought back. They declared independence. Calling themselves the Conch Republic after the trademark crustacean home, passports were issued and foreign aid requests went out — admittedly, all with a tongue-in-cheek approach.
It was all a little too embarrassing for the U. S. government, which quietly dismantled the checkpoint, but not before creating a lasting mark recalled each time you spot a fluttering Conch Republic flag.
And that’s exactly what makes a place like this so desirable — not only do I feel like I’m visiting a community that knows how to party and not take itself too seriously, that same community knows it’s part of something worth fighting for, preserving and sharing with anyone willing to leave their baggage at an imaginary checkpoint before heading there.