The Songlines of Key West: The Conch Republic, Unscripted

Travel Stories: In a three-part series, Bill Belleville burrows deep into the spirit of the mythic island. Part three: Into the mystery of the twilight.

01.09.09 | 9:35 AM ET

Photo by Michelle Thatcher

It is late in the day and Mallory Square is packed with tourists waiting for the sun to dip into the sea. While they wait, sword swallowers and tight rope walkers and fire eaters are busy at work, creating a grand street theater. It is a celestial sort of sideshow, really, an event in which applauding a natural act implies you are as island savvy—perhaps even as whimsical—as the locals. 

This is my last night in Key West, and so I am walking away from Mallory Square, intent on a sunset experience that’s just a bit less known, and far less packaged. 

La Concha, a pink stuccoed hotel built in 1926, seems a righteous option. It not only has a seven-story rooftop view—it’s brimming with a retro history that predates the Mallory docks. 

My friend Michelle and I are joined by Steve Harris, an old bud from Key Largo. Steve’s an excellent writer who makes hard cash tending bar and taking tourists for sunset charter cruises on his sailboat. He’s a big, good looking guy who’s also a hopeless romantic, naming his boat Caduceus for the magical staff welded by Mercury, the Messenger God, to summon the other gods to earth. “You know,” says Steve, “the dreams of heaven can be right here in this moment, if we really want them to be.” Steve truly appreciates the onionskin nature of Key West in which the cultural peel of each thin layer reveals yet another beneath it. 

MORE ON KEY WEST: Slideshow | Part one: Doing the Duval Crawl | Part two: The Other World.

The three of us walk into the La Concha lobby, restored to its 1920s charm, back when the island was flush with free-spending rum runners, and adventurous tourists rode here on Henry Flagler’s Overseas Railroad. We take the old elevator up to the rooftop, grab some cold Heinekens from the bar there and head outside to watch the coming twilight settle around us. From here, I have a frigate bird’s rare view of shiny metal rooftops and royal poincianas that explode in glorious orange bloom, from one end of the island to the other.

I look over the edge and seven stories below see the wild chickens clucking their way down the streets, the pedicabs of tourists with their skin as red and peeling as the gumbo limbo tree, and way off to the west, I see Mallory Square and the Gulf. I think of Hemingway’s fictional Henry Morgan who saw the top of La Concha jutting out of the low cover of green and tin that was 1930s Key West from his sailboat at sea. 

There are maybe 30 other people up here, kicked back, just hanging out. The sun sets rather unspectacularly, the group applauds, and most then leave. Steve suggests we go to the other side of the rooftop. “Let’s go watch the moon rise,” he says. “I think it’ll be a lot neater than the sunset.” 

We do, and it is, not quite full but white and luminous in the scarlet of the island twilight. Steve tells me Tennessee Williams finished writing “A Streetcar Named Desire” here in a two room suite at the top of La Concha before later buying his home on Duncan Street in the 1940s. And, back in the 1920s, Pan Am based its Key West to Cuba office in the hotel. This helps explain the lobby of paneled tropical wood, and how it reminds me of hotels I had seen in Havana, like the Ambos Mundos where Hemingway stayed. In Papa’s world of “To Have and Have Not,” dark rum would be the drink here, rhumba the dance. 

Still, myth again approaches art: Local tourism legend has it that Williams, downing a gin and tonic, was the very first to applaud the Key West sunset at Mallory. I am guessing this is like most stories about Key West, of the sort you hear tour guides give when the Conch Train weaves past you on the street. It seems like the kind of thing that could happen, and that’s likely all the truth that is needed.

We head down from the La Concha rooftop, walking beyond the Green Parrot bar toward Bahama Village. It’s the last section of the old town still not fully gentrified, a place where descendants of Bahamian spongers live in modest Conch houses, intimations of an earlier island everywhere you look. When Papa lived on Whitehead Street and wrote “To Have and Have Not,” the contrast between wealthy visitors and Conchs informed the title and the narrative: “He did not take the bicycle but walked down the street. The moon was up now and the trees were dark against it and he passed the frame houses and their narrow yards, light coming from the shuttered windows ... Conch Town ... where all was grits and boiled grunts.” Unlike so many other vintage descriptions, this one still works, and works very well. 

At Petronia Street, we walk under an old metal portal with a colorful seal for “Bahama Village” in the middle of it. Michelle stops under a large traveler’s palm nearby and holds out her arms, imitating the upward splay of its leaves. 

Nearby is the Blue Heaven Restaurant, two-story pinewood with tin roof, blue shutters and a courtyard where most of the food is served on handmade tables. Tropical foliage bushes up from every corner, almond and Spanish lemon trees, with a lush royal poinciana canopy overhead. To the side of the courtyard, two guys are playing ping pong at a table, and chickens are pecking about, no worries about ever crossing a road. Jimmy Buffett once wrote and sang of a “Blue Heaven Rendezvous”—a place where there’s “still some magic left in this tourist town”—and the lyrics fit perfectly. 

Back on the street, it’s quieter now, no neon and noise, just the lightest scent of a trade wind breeze picking up off the water from somewhere, as it should be. We walk deeper into Bahama Village, moving a few years back in time with every step. I hear dominos being slapped down on a table from somewhere nearby, low murmuring, the click of glass. I know many of the trees from years of traveling in the Antilles: Kapok, Jacaranda, Poinciana, Orchid, descendants of seeds riding here on the Gulf Stream, opportunistic like the early pirates and wreckers. 

I hear James Brown singing “I Feel Good” from a yard, inside a brightly painted picket fence hung with lobster and stone crab trap buoys. A very affable man looks up from tinkering with a three-wheel bicycle, and invites us into his yard. His eyes are bright and his mustache is white. The bike seems like a miniature parade float, a wonder of low-tech whimsy, cobbled together by our host—so it appears—just for the sheer fun of it all. 

The bike architect is James Chapman, who is somewhere in his 60s. “The street’s named after my family” he says, pointing to a sign that reads “Chapman Street.” James grew up here, right in the house behind us. “Played marbles as a kid, made tops, and kites and yo-yo’s. It got so I could build anything I wanted, just to have fun with it,” he says. What James has fun with now is his bike, which has a large box behind the seat. Atop the box are two foot-high figurines he crafted. “This one would be James Brown,” he says, “and that would be Louis Armstrong.” 

James reaches somewhere into the box and toggles a switch and James Brown begins to feel good again. James rings a bell on the handlebars, and presses another button that blows a horn. James shows us an oil painting an artist did of his buddies, all fishermen, sitting on the porch, playing cards. “All good guys,” says James, remembering each of them by name. He stops, spreads his arms, points to a tree overhead. “This here’s a sappy-dilly. You can make good ice cream with its fruit,” he says.

And across the street is a banyan tree. “The white crowned pigeon likes it,” he says. James shows us some ice tongs he used when he sold ice. When he was a kid, he shined shoes. “I’ve done whatever I’ve had to do,” he says. 

Michelle asks about the fanciness of the modern island, and how people respond to it now. James pauses, smiles widely, as luminous as the moon rise. “They just don’t understand ... that Key West is not part of the United States.” And he is right: The new transient wealth is just another skin peeled away, or added; the core of the place remains. 

We thank James for his time in his yard, the music on his bike, and say goodbye. All else that makes no sense to me about this strange island in the stream dissolves, and I walk into the tropical night exhilarated with the knowledge that an unscripted Key West still endures here, out on the turquoise water, at the top of a half-fictional hotel, in someone’s back yard, under a sappy dilly tree. 

I search for a way to understand this, something profound maybe, but all I come up with is a shard of another Buffett lyric:

What makes it all happen is still a mystery to me.

MORE ON KEY WEST: Slideshow | Part one: Doing the Duval Crawl | Part two: The Other World.