Key West Florida — Retro Vintage History

What's with the Conch Republic? In April 1982 the U.S. Border Patrol threw up a roadblock on U.S. 1 just north of the Keys, stopping and searching every car coming off the islands — and the traffic, and the tourist season, ground to a halt. Key West's response was pure Key West: on April 23, 1982, the city declared itself an independent nation, the Conch Republic, symbolically seceded from the United States, broke a loaf of stale Cuban bread over the head of a man in a navy uniform, surrendered one minute later, and applied for a billion dollars in foreign aid. It was theater — but the roadblock came down, and the Conch Republic stuck. The flag still flies, the motto is "We Seceded Where Others Failed," and locals are Conchs, born on the island, or freshwater Conchs once they have stayed seven years.

The name is older and stranger. Spanish charts called the island Cayo Hueso — Bone Island — and the story goes that early sailors found it scattered with the bones of a long-ago battle; English tongues turned Cayo Hueso into "Key West." Calusa people and Cuban and Bahamian fishermen worked these waters long before. In 1822, a year after Florida passed to the United States, John Simonton bought the island, the U.S. Navy raised its flag under Lieutenant Matthew Perry, and a town began at the end of the reef — the southernmost city in the continental United States, ninety miles from Cuba.

For its first decades Key West got rich off disaster. Ships ran aground on the coral reef offshore with such regularity that salvaging the wrecks — "wrecking" — became a licensed, court-supervised industry, and the men who hauled cargo off the reefs made the town, by the 1830s, the wealthiest city per capita in the United States. Salt ponds, sponging, and sea-turtling followed. Those fortunes built the first grand houses of Old Town and gave Key West a worldly, seafaring character it never lost.

Cuba was always close, and in 1868 the cigar industry crossed the Straits. Cuban makers brought their trade to Key West, and for a generation the island was a cigar capital, its factories turning out millions of hand-rolled cigars and its streets filling with a Cuban community whose San Carlos Institute still stands on Duval Street as "La Casa Cuba." A great fire in 1886 and years of labor trouble eventually sent much of the industry north to Ybor City in Tampa, but the Cuban-American heritage stayed rooted on the island.

For a time the island was the end of a railroad. Henry Flagler pushed his Florida East Coast Railway across open water from key to key, and in 1912 "Flagler's Folly" reached Key West — an engineering marvel that linked the island to the mainland for the first time. The Labor Day Hurricane of 1935, a Category 5 storm, destroyed the line and took hundreds of lives, many of them World War I veterans working in the Keys. The roadbed was rebuilt for cars, the Overseas Highway opened in 1938, and U.S. 1 now runs the length of the Keys and ends here, at Mile Marker 0.

The Navy made Key West a base — a submarine station from the 1930s on — and the warm island drew writers and presidents. Ernest Hemingway kept a house at 907 Whitehead Street from 1931 to 1939, a place built of native limestone in 1851 and still known for the descendants of his six-toed cats. Tennessee Williams wrote here for decades. And Harry Truman so loved the old naval officers' quarters that they became his Little White House, where he ran the country through the winters of his presidency. The literary-and-presidential Key West remains a pilgrimage.

Our Key West logo carries the Florida alligator above "Florida Territory — Est. 1845," the shared retro emblem of our Florida towns, drawn in worn black-and-white like an old woodcut crate label. The 1845 date marks Florida statehood, and the alligator is the through-line that links Key West to every other Florida town we make. The detail that makes this one Key West is the island itself — the Conch Republic at the end of the Overseas Highway, the Southernmost Point, and Mile Marker 0 where the road, and the country, finally run out.

Key West is Mile Marker 0 — the end of the road and the start of the Conch Republic, the southernmost city in the country, ninety miles from Cuba, where the wreckers got rich off the reef and the sunset is a nightly event. Our Key West designs gather that into wearable form. Wear the Conch Republic. Wear Mile Marker 0. One Human Family.

Key West, Florida — Travel Guide

Visiting Key West Today

Key West sits at the end of the Overseas Highway in the Florida Keys, the southernmost city in the continental United States and the seat of Monroe County. Expect the pastel conch houses of Old Town, the galleries and bars of Duval Street, the famous Hemingway and Truman houses, the nightly sunset gathering at Mallory Square, and easy water on every side. It is warm, walkable, and bike-friendly, busiest in the winter high season from December through April.

Old Town, the Landmarks & the Water

For visitors looking for things to do in Key West, Florida:

• Photograph the Southernmost Point buoy at Whitehead and South streets — the marker ninety miles from Cuba.
• Tour the Hemingway Home & Museum on Whitehead Street — the 1851 house, its gardens, and the famous six-toed cats.
• Visit Harry Truman's Little White House, the president's winter retreat in the old naval quarters.
• Watch the Mallory Square sunset celebration, with street performers, music, and the harbor lit gold.
• Stroll Duval Street and Old Town's lanes for galleries, shops, and Bahamian-style conch-house architecture.
• Walk the beach and brick ramparts of Fort Zachary Taylor Historic State Park at the island's edge.
• See the recovered treasure of the wrecking and salvage era at the Mel Fisher Maritime Museum.
• Take a ferry or seaplane seventy miles west to Dry Tortugas National Park and Fort Jefferson.

Why People Visit Key West

Key West rewards travelers who want history, water, and a freewheeling island culture rather than only a beach — the Southernmost Point, the Conch Republic, the literary and presidential houses, and a compact Old Town you can walk end to end. People come for the sunset at Mallory Square and the bars of Duval, for the Hemingway and Truman landmarks and the wrecking-era treasure, and for an easygoing day at Mile Marker 0 where the Overseas Highway, and the country, finally run out of road.

For deeper reading on the Key West history described here — the Cayo Hueso name and the Calusa and Cuban and Bahamian fishing camps, the 1822 Simonton purchase, the wrecking and salt and sponging trades, the Cuban cigar era and the San Carlos Institute, Flagler's Overseas Railroad and the 1935 Labor Day Hurricane, and the literary and presidential houses — it may be useful to consult (1) the Key West Art & Historical Society at the Custom House, (2) the Monroe County Public Library's Florida History Department, (3) the Mel Fisher Maritime Heritage Society, (4) the State Library & Archives of Florida, and (5) the Florida Historical Society. For travel and visitor information, it may be useful to contact (1) VISIT FLORIDA, (2) the Monroe County Tourist Development Council (The Florida Keys & Key West), (3) the City of Key West, (4) the Florida State Parks office, and (5) the Key West International Airport visitor desk.