By: Jay Brida
Photos: Shutterstock, Corbis, Offset, Getty Images
The Florida Keys, a string of hundreds of coral cay islands, begin just 15 miles south of the Miami city limits and stretch on for 125 miles, marking the border between the Atlantic Ocean and the Gulf of Mexico. At the end of those islands, and the Overseas Highway that connects most of them, is Key West. For the continental U.S., it is literally the end of the road. The people who live there, and those who love it, embrace this literal and figurative finality and have made “the end” a kind of cultural motto.
The story of the end in Key West may as well start in the farthest reaches of northern Maine, where U.S. Route 1 begins in Fort Kent. From there, it winds down the Eastern Seaboard, going through the BosWash megalopolis and the coastal South before ending at the intersection of Whitehead and Flagler in Old Town Key West. You could say that’s where it starts, too, but you’d be hard-pressed to find any locals who agree.
Instead, they cultivate a sense of finality. After miles and miles of glimpses of the turquoise sea on the highway that meanders through small cites and tiny keys, city and island marks the last of land, the southernmost point of the U.S., before you hit Cuba, some 90 miles farther south. The locals know it’s a terminus, not a beginning, and a mirrored mindset surfaces in its description by a motel in Fort Kent, which proclaims “This is where it all begins.” Key West is a place people end up—sometimes for a couple months, a few years or the rest of their lives.
Everyone has their stories: A self-described newcomer who has “only” been there 21 years. A guy who was about to close a big deal but, inevitably, the deal fell through and he got on his boat and found anchorage in Key West. The woman who moved from New England when she was young and now, 20 years later, is a fixture of the community, covering shifts at bars and restaurants for friends who decide not to come in for various reasons.
It’s also not hard to see why people stay. The pace is agreeable. The air is languid and seductive. The back coves, small beaches and water are truly beautiful. There’s world-class snorkeling, Southern charm and great food. No one cares enough to judge why—or even show much interest in the answer if you choose to share it. The only thing that seems to really move people to standing ovations is the nightly show at Mallory Square, where people gather to watch, and celebrate, the sunset. A woman I spoke with has cataloged each one for the past 10 years and posted the results on her Facebook® page. “It keeps me plugged in to what matters to me. There’s not all that much to do, but there’s all of this,” she said, showing me the previous night’s sunset on her phone.
Key West has long curated this reputation. This is the self-described Conch Republic, where eccentricity is not simply tolerated but embraced. Here, pro golfers and country stars rub shoulders, usually exposed, with fishermen and part-time wind-surfing waiters. The bar scene is the stuff of legend, and days at one of the countless pubs can start early and end earlier the next morning. Party cruises, yachties and deep-sea fishing trips provide an armada of pleasure craft for people to charter.
It seems that people come to Key West not simply to unwind but to forget the entire thought of winding altogether. A few celebrated clothing-optional bars dot the Old Town, which seemed superfluous during the pre-Halloween week when I was there and many people seemed to wear only body paint and strategically placed sequins or balloons. Or less. But everyone moves with a casual stride and a half-smile, just happy to be part of the shambling parade and the good time.
Ernest Hemingway is a dominant ghost here for plenty of mutually reinforcing reasons. It’s where he wrote Farewell to Arms and made claim of bringing in an astringent daiquiri he helped create in Havana—to say nothing of inspiring the setting for his book (not the movie) To Have and Have Not. Tennessee Williams is another giant American writer who made his way down to the Keys, drawn to the openness of the culture—or maybe the steamy drama that felt very public. People mention that it was the only place where the playwright ever owned a house. Harry Truman was another habitué of Key West and vacationed here often during his presidency, setting up a southern White House not too far from the Hemingway house, both of which now stand as museums.
If there is a feeling of “beginning” here, it’s that this might mark the geographic start of Caribbean culture. Cuba, in particular, holds a strong gravitational pull in the Key West mindset. Havana, after all, is much closer than Miami. You see it in the architecture and the cuisine, with strong Cuban coffee and Cubano roast pork sandwiches providing grist for breakfast. A previous mayor famously waterskied all the way to the island for no other reason than no one had done it before.
There’s more, too, that makes it feel like it is part of the Caribbean. The mangrove swamps. The gently swaying palms. The powder-blue water. The vibe.
Driving north after several days there, I felt like I had to re-acclimate to the mainland. The roads are more open and easily transversed. There are fewer scooters blocking your way. Fewer roosters. A lot more stress. Even Miami felt a bit buttoned-up. But my mind wandered to the seductive pull of slow, loping strides down toward the western side of the island, drink in hand, to watch the sun slide into the water and leave behind the firecracker reds and coral pinks before heading back to Duval Street and the human carnival of the Key West night.
The end feels just right.