I FIRST WENT TO Key West with my family as a fourth grader. My father drove us around the island in a couple of hours. I’m not sure that we ever got out of the car except to have milkshakes on a narrow, remote beach. More than anything, my parents loved to act unimpressed by famous places. Before sundown, we got back in the car and drove to a Holiday Inn in Miami for a good night’s sleep before our Bahamas cruise the following morning.
A few rules about Key West...
Rule number one: You don’t drive around Key West. You cover it on the ground.
Rule number two: At some point Key West will be your final destination, not a side trip.
I ran away from a job a year after my high school graduation and met an older guy in the Jacksonville Greyhound station. We rode the bus straight to Key West holding hands, then stayed in a weathered Victorian-house-turned-motel locally known as the Tiltin’ Hilton. I had never suffered such glorious dilapidation. I was nineteen, attempting a romance in a town that was falling, again, on hard times — this one because of AIDS. I was a college dropout but I had been doing my reading. We were two years into a disease that was thinning out crowds in every community. At the Tiltin’ Hilton, I selected paperbacks from a pile, all by authors who’d lived there or made long, seasonal stops in Key West, and I mourned the passing of a time I would never know: the Key West of Steinbeck, Herlihy, Capote, Vidal, Bishop, and Tennessee Williams.
I wouldn’t return to the island for 12 years, this time with my partner, author Edmund White. Suddenly I was in the company of living writers in their prime: Robert Stone, Ann Beattie, Annie Dillard, John Malcolm Brinnin, Joy Williams, Alison Lurie. It is fashionable to say of any place that its sheen has gone off. What’s great about Key West is that if you look closely enough on your strolls, it still wears the pockmarks and flaking paint of its sleepy, impoverished past. You see patinas of history going back 200 years or longer — wood cured by the elements or the lace of keyhole-sawed gingerbread woodwork, flaking and awaiting renewal. In the subtropical honey light, you realize that even though you’re in the United States, you’ve never been anywhere in the world like this.
'How did you go bankrupt?' Bill asked. 'Two ways,' Mike said. 'Gradually and then suddenly.'
Since the late nineteenth century, poets and pamphleteers have lured northerners looking for paradise to the coasts of Florida as a destination of rest and forgetfulness. But Key West is anything but innocent. It has hosted pirates and swindlers, bootleggers and tax refugees, political exiles and mad schemers whose dreams were wrecked by hurricanes, debt, or cheap easy drink. It lures the romantic on the run whose default sensation is “Maybe this time.”
Key West is not a great beach town — although it has passable beaches, they are mostly composed of imported sand. That the island doesn’t resemble the Caribbean or South Pacific is part of the point. To look at it from the air or street level, you’d perceive a southern town. Going inside any number of places, you breathe bohemian values. At lunch, you may be served by a French immigrant who doesn’t care if she ever sees Paris again. People move or go to Key West intentionally. Often, you hear the story of the vacation that led to the migration. People with perfectly good jobs in the Midwest throw it all away to live in a tiny apartment, paces from a haunt where their new friends are drinking beer and waiting to join them for karaoke.
Key West is old houses and sportfishing docks. It’s hotels and restaurants and cruise ships that disgorge for the afternoon. And it’s the constant friction of people who come from all over that forces everyone to get along, the drag queen beside the Dayton dry cleaner. For as long as Key West has been a tourist town, there has been something aspirational about all this felicity and fun.
Rule number three: There will always be another place where people greet you without a single hesitation. It is a special, special place, and its appeal can’t be described.
In “To Have and Have Not,” one of Hemingway’s only two novels set on these shores, a busted millionaire has harbored his yacht in the Key West harbor, biding his time.
“How did you go bankrupt?” Bill asked.
“Two ways,” Mike said. “Gradually and then suddenly.”
I made friends with bartenders and restaurant owners, all of whom had elected to make Key West their home. I go home from the bars at their 4 a.m. closing. The streets are lit from above, streaking down light through the arches of trees that mimic curving cathedrals made from bent branches. There is a perfect silence. You have lived an entire life in a few hours. And you’re now alone.
This solitude is Key West, but it is not a nervous or agitated solitude.
You’ve breathed the subtropical air. You’ve witnessed the changing light. And you’re alive. More than anything, you’ve toured the town that tells you that life is interesting; it isn’t only what you’ve known back home. Drunk and happy, you finally get this sensation.
To be honest, in coming here with Ed for 25 years now, I didn’t originally take to the town’s languid pace. Even on the most beautiful days, I was locked in my room trying to write something startling and original. I was kind of missing the point. I should have been outside exploring. The point of Key West is the people who inhabit and invade it. Eventually, I understood that Key West was about the stranger, like you. The stranger who longed for something different, something refreshing. Strangers in the street — whether they’re guest-housing or stepping off a cruise ship for the day — have instinctively found their own peculiar reason for washing up here.
Michael Carroll's Guide to Key West
From his favorite places to ponder Key West’s history to glorious ramshackle cafes to imbibe the spirits, author Michael Carroll shares his favorite sites on the storied archipelago.
Audubon House and Tropical Garden
A visit to Audubon House is like a trip into the sumptuous past via this family home built by Captain Geiger. Once the largest city in Florida, Key West grew resplendent from the shipping industry in the nineteenth century, and Audubon House sparks the imagination about the bygone days on this hopping-off point to the Caribbean. Slated for destruction after the house passed out of family hands, it was saved by a rich donor in the 1960s, and named for its most famous extended guest, naturalist and painter John James Audubon. Its decor is unpretentiously elegant, with gorgeous tropical plantings and an unhurried atmosphere.
La Te Da Hotel
La Te Da isn’t from the Diane Keaton line in “Annie Hall,” rather, it's short for La Terraza de Marti or the balcony of (José) Marti. Its original owner, Teodoro Perez, was a local cigar manufacturer and an active part of the Cuba Libre movement, sending money and arms to Havana with help from proceeds from his factory. Today, La Te Da is a meeting spot for Americans who might not otherwise mingle with tourists from around the world, who come to dine and drink in the shade. I highly recommend the yellowtail snapper Reuben. At night, it becomes an important entertainment hotspot with well-orchestrated drag shows.
Originally opened in 1909, Pepe’s describes itself as “ramshackle.” Sit inside and you’re surrounded by rustic stained wood. Sit outside on the brick patio in the shade of trees or at the cozy bar, and there you are talking to America again. Go for oyster happy hour and get half-priced Apalachicola oysters and beer. It’s all very Buffett, and I don’t mean Warren. This place is famous for their comfort dishes, fresh fish offerings, and did I mention cold beer?
Cuban Coffee Queen
With more than one laid-back location on the island, this barely more than a coffee and sandwich stand serves everything fresh and tasty. They've got the strongest coffee on the island, and the most galvanizing sandwiches when you’re famished before a night out or during a morning hangover.
Bobby’s Monkey Bar
Bobby’s is a place where gays and straights are not afraid to get together for near-nightly open-hearted karaoke. At times, the crowds are so intensely training their eyes and ears on the stage, you’d think it was an episode of “The Voice.”
Michael Carroll Writer
Michael Carroll is the author of "Little Reef and Other Stories," which won the Sue Kaufman Prize for First Fiction from the American Academy of Arts and Letters. His second collection, "Stella Maris: And Other Key West Stories," was published in 2019 by Turtle Point Press.
Mark Hartman Photographer
Mark Hartman is a photographer and director based in New York City.