Consider: Key West
At the end of US 1, the party has just begun.
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Every week in Considered, we feature an object or place that has endured and the lessons we can learn from it. Today’s topic was inspired by a recent issue of Yolo Intel, my favourite travel newsletter. The issue featured a great post by Alex Postman (aptly named) on Key West that sparked enough curiosity to learn more. This town of 25,000 is more interesting than some cities of 5 million. Let’s dig in.
Key West, FL, lies at the very tip of the United States. It is actually closer to Havana than Miami. If you take the US Route 1 highway all the way to its end, you find yourself on the island of Key West.
The island’s history begins with its first inhabitants, the Calusa and Tequesta, two Indigenous tribes. They were forcefully removed to Cuba in 1763 when the island was transferred by Spain to the British. For the next hundred years, Key West was sparsely inhabited and used by fishermen and “privateers” (aka PIRATES, ARRRRR). Like much of Florida, Key West has a history of shady land transactions. Deeded to a Spanish naval officer named Juan Pablo Salas in 1815, Salas then sold the same land deed to two separate people at the same time. Once for a boat and once for the equivalent of $2,000. The second purchaser, John Simonton, won out (and he later sold the island to three individuals at the same time) and the island became part of the United States in 1822. Shortly after the boom times began.
In the 1830s, Key West was the richest city per capita in the United States. (Who knew key lime pies were so lucrative?) The reality is a bit more opportunistic. Key West is surrounded by one of the largest coral reefs in the world, and at that time most goods were transported by sail boats (big ones, but still sail powered). The weather could be unpredictable and many of the boats ran aground. All kinds of salvaged goods flowed through the Key West port, like cotton, tobacco, silver utensils, clothing, even locomotives and pianos. How the industry worked was that a ship would get damaged on the reefs around Key West and a “wrecker” would race out to stake their claim to the sinking ship. Once the cargo was recovered and brought ashore, an auction would be held and a judge would determine how to divide the proceeds between the wreckers and the ship’s original captain. To give you a sense of the scale of this, the National Oceanic and Atmosphere Administration (like earth NASA) says that there are still over 1,000 shipwrecks in the reefs around Key West.
Steam ships ended the wrecking trade by being easier to steer and less reef-collision prone. Their wide adoption led to the end of the wrecking trade. Some faithful held on. In 1985, after 20 years of searching, local resident Mel Fisher discovered part of the wreck of a Spanish galleon that contained $400M in gold and treasure. He opened a museum to display some of his findings.
Parallel to the wrecking trade, Key West became a tourist destination (for which it is still well-known today). It started with celebrities and literati, then Parrot Heads and then LGBTQIA+ travellers finding a home there.
Hemingway and Tennessee Williams were some of the most well-known residents of the city. Hemingway arrived in 1931 and left in 1939. During that period he wrote Death in the Afternoon, his stories of the Spanish Civil War and began work on For Whom the Bell Tolls. His house was one of the finest on the island and one of the first to have indoor plumbing. It was also the first to have a second floor bathroom, which was enabled by the installation of a rooftop rain water cistern. If there was a drought, did he have to go downstairs to do his business? The answer is lost to history. His home is actually open for tours.
Hemingway was the proud owner of a six-toed cat that was a gift from local mariner, Captain Stanley Dexter. Hemingway’s children named the kitten Snow White. The museum grounds are littered with miniature gravestones marking the lives of his six-toed friends.
Shel Silverstein spent the last years of his life in Key West and Judy Blume owns a local bookstore there. She can often be found riding her bike around town.
Tennessee Williams was another long time resident and is credited with starting the island’s reputation as an LGBTQIA+ vacation destination. He visited and lived in Key West from 1941 until his death in 1983. Local lore has it that he wrote the final draft of A Streetcar Named Desire as a guest at the La Concha Hotel in Key West in 1947. He moved there full time in 1949 and in 1950 bought a house at 1431 Duncan Street that was his home for 34 years. The house is still a private residence, but there is a Tennessee Williams Museum in town. Other notable LGBTQIA+ authors and playwrights made the move to Key West as well, including Jerry Herman who composed Hello, Dolly! and La Cage Aux Folles. Now over 1/3 of the city’s residents identify as LGBTQIA+, and Key West welcomes 300,000 queer tourists ever year.
The last contingent that calls Key West home are the Parrot Heads. Key West has the important distinction of being home to the first Margaritaville restaurant. There are nightly sunset celebrations, Fantasy Fest (which has replaced Halloween on the island) and the annual Parrot Head Convention, the “Meeting of the Minds.” Duval Street, which is 14 blocks long and bisects the island, is a 2km long happy hour at all hours of the day. It is fitting that Jimmy Buffet popularized the saying “It’s 5 o’clock somewhere!”. It’s always 5 o’clock in Key West.
My first exposure to Key West came through CNN’s New Years Eve Live. Since 2017, besties Anderson Cooper and Andy Cohen have co-hosted the NYE special, barely making it through the night. With other hosts in New Orleans (famously Don Lemon getting drunk in a hot tub) and Key West, viewers can enjoy Sushi the Drag Queen in the annual Key West Shoe Drop. It is as wild as it sounds, and a clip is below.