Key West

Key West has one of the most colorful and layered histories of any American city, shaped by geography, smugglers, wreckers, and artists alike. The island was originally inhabited by the Calusa people, who called it “Cayo Hueso” (Island of Bones) — likely a reference to skeletal remains they left there. Spanish explorers encountered the island in the early 16th century, and the name was eventually anglicized to “Key West.” Spain ceded Florida to the United States in 1821, and the island was quickly claimed by American entrepreneur John Simonton, who purchased it for $2,000. Key West’s first great industry was wrecking — salvaging cargo from ships that ran aground on the nearby reefs. The Florida Keys sit along one of the most treacherous shipping lanes in the Western Hemisphere. By the 1830s, Key West was the wealthiest city per capita in the United States, with licensed wreckers competing to reach downed ships first. The introduction of reliable lighthouses in the 1850s gradually killed the industry. Two industries replaced wrecking. The sponge industry flourished in the surrounding waters until a blight wiped out the sponge beds in the 1930s. More dramatically, Cuban cigar makers began relocating to Key West in the 1860s, especially after Cuba’s Ten Years’ War (1868–1878). By the 1880s, Key West had over 100 cigar factories and was Florida’s most populous city. Cuban revolutionary José Martí visited Key West multiple times, raising funds and support from the exile community there. Henry Flagler extended his Florida East Coast Railway to Key West in 1912, an engineering marvel called the “Eighth Wonder of the World.” It connected the isolated island to the mainland for the first time and was expected to make Key West a major commercial hub. However, the Labor Day Hurricane of 1935 — one of the most powerful Atlantic hurricanes ever recorded — destroyed the railroad. It was never rebuilt. The roadbed was converted into the Overseas Highway, completed in 1938 and is still the only road to Key West today.

By the 1930s, Key West was bankrupt and in ruins — nearly half the population was on relief. In a desperate move, the city essentially handed control to the federal government. The Federal Emergency Relief Administration (FERA) rebranded Key West as an artists’ and tourists’ destination, invested in infrastructure, and promoted the island’s unique charm. It worked. Ernest Hemingway had arrived in 1928 and his presence helped cement Key West’s literary and bohemian reputation.

Key West had been a naval station since the 1820s, and WWII brought enormous military investment. The Navy expanded dramatically, and the island became a critical base for anti-submarine operations in the Atlantic. President Truman made Key West his “Little White House” — his preferred vacation retreat — visiting 11 times between 1946 and 1952. In 1962, Key West was on the front lines of the Cuban Missile Crisis, with military assets massed on the island just 90 miles from Cuba. Twenty years later, in 1982, the U.S. Border Patrol set up a roadblock on US-1 to check for drugs and illegal immigrants, causing a massive traffic backup. In protest, Key West Mayor Dennis Wardlow declared the “Conch Republic” — a mock secession from the United States — then immediately surrendered and asked for foreign aid. The stunt became legendary and is still celebrated today. Today Key West is defined by its tolerance, eccentricity, and tourism. It became a major hub of LGBTQ+ culture from the 1970s onward, and the annual Fantasy Fest (since 1979) reflects its anything-goes spirit. The island balances its role as a major cruise ship destination with a fiercely local identity — “Conch” being a badge of honor for those born here. It’s a place that has always lived slightly outside the rules — geographically, legally, and culturally.

Neither Kim nor I have ever been to Key West for some reason. Since we decided we were overdue for a trip to Florida to visit friends, we would take advantage of the occasion and spend a few days figuring out what Key West was all about. We are staying at the Simonton Court Inn right in town, a place obviously named after the founder of this island. It’s a random and pleasant array of cottages set amongst the Palmetto trees with uneven brick sidewalks, and pathways with an array of small swimming pools designed to dip into in the afternoon to wash the tropics off. Our two nights here will cost one half of what Simonton originally paid for the entire island. Last night we walked to a nearby restaurant down a quiet city street and then walked home down the much busier main drag of Duval Street. So far this seems like a cross between a small town of the Deep South and every coastal tourist town you’ve ever been to.

Today we will see more of the town with Kim’s friend Jim, who lives here in Key West. After getting a look at Jim’s wonderful old Key West home, we went for lunch at Louis’ Backyard, a popular spot on the south coast beach. We then walked around and enjoyed the Casa Marina, which is Key West’s version of the Breakers, built by none other than Henry Flagler, the guy who connected Key West to the mainland with his railroad. And then, in the afternoon we drove past the Truman Little White House and through the Fort Zachary Park to see what they’re about. Our big stop was at the Hemingway House, where we toured where the great man wrote his novels in the 1930’s. I’m not sure there’s much else to do here in Key West other than sit on the beach and wipe off the sweat and guzzle rum, but if there is, we’ll figure out how we can do it later today because we leave tomorrow to take our drive up through the other Keys to the main East Coast of Florida…the belly of the American beast in the era of Trump.