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History of Key West

Key West is a beautiful, laid back, eclictic city with beautiful houses and so much history. We were anchored out near Wisteria Island off the coast of Key West. We met so many people that beamed about the strong history and influence of Cuba and the rich heritage of the city so I had to do some research on Key West and find out what’s what. We spent three weeks here and really enjoyed exploring the city, talking to the eclectric people and discovering recommended venues.




Key West has a strong connection with history and culture. This is apparent in the Victorian and Colonial architecture of conch cottages and mansions preserved throughout Old Town, as well as many long-standing, locally-owned restaurants, bars and businesses.




The history of Key West is that Cayo Hues or Kajo ˈWeso is the original Spanish name for Key West and it means "bone cay". Cay is a low island or reef with no fresh water source. It is said that the island was littered with the bones of prior native inhabitants, who used the island as a communal graveyard. Creepy!


The years in Key West time:


1521 Spanish explorer Ponce de Leon first discovered Key West during his expedition to Florida in search of the Fountain of Youth. He claimed the island for Spain and named the island Cayo Hueso, which means Bone Island. Cubans and Bahamians regularly visited the Keys, the Cubans primarily to fish, while the Bahamians fished, caught turtles, cut hardwood timber, and salvaged wrecks. Smugglers and privateers also used the Keys for concealment.


1763 Great Britain took control of Florida from Spain.


1766 the British governor of East Florida recommended that a post be set up on Key West to improve control of the are. The Bahamians apparently set up camps in the Keys that were occupied for months at a time, and there were rumors of permanent settlements in the Keys.


1815, the Spanish governor of Cuba in Havana deeded the island of Key West to Juan Pablo Salas, an officer of the Royal Spanish Navy Artillery posted in Saint Augustine, Florida.


1821 Florida was transferred to the United States in 1821, Salas was so eager to sell the island that he sold it twice. The first sales was for a sloop valued at $575 to a General John Geddes, a former governor of South Carolina. The second sale was to a U.S. businessman John W. Simonton, during a meeting in a Havana café on January 19, 1822, for the equivalent of $2,000 in pesos. Geddes tried in vain to secure his rights to the property before Simonton who, with the aid of some influential friends in Washington, was able to gain clear title to the island.


Simonton had wide-ranging business interests in Mobile, Alabama. He bought the island because a friend, John Whitehead, had drawn his attention to the opportunities presented by the island's strategic location. John Whitehead had been stranded in Key West after a shipwreck in 1819 and he had been impressed by the potential offered by the deep harbor of the island. The island was indeed considered the "Gibraltar of the West" because of its strategic location on the 90-mile wide deep shipping lane, the Straits of Florida, between the Atlantic Ocean and the Gulf of Mexico.


John Simonton subdivided the island into plots and sold three undivided quarters of each plot to John Mountain, John Whitehead, and John W. C. Fleming.


John Mountain resold his quarter to Pardon C. Greene, who took up residence on the island. Greene is the only one of the four "founding fathers" to establish himself permanently on the island. He was a member of the city council and also served briefly as mayor.


John Whitehead, his friend who had advised him to buy Key West. John Whitehead lived in Key West for only eight years.


John W.C. Fleming was English-born and was active in mercantile business in Mobile, Alabama, my home town, where he befriended John Simonton. Fleming spent only a few months in Key West in 1822 and left for Massachusetts, where he married. He returned to Key West in 1832 with the intention of developing salt manufacturing on the island but died that same year.


John Simonton spent the winter in Key West and the summer in Washington, where he lobbied hard for the development of the island and to establish a naval base on the island, both to take advantage of the island's strategic location and to bring law and order to the town.


The namesakes of the Old Town streets are of these gentlemen. However, Duval Street is named for William Pope Duval, the first territorial governor of Florida.




1822, Lt. Commander Matthew C. Perry sailed the schooner Shark to Key West and planted the U.S. flag, claiming the Keys as United States property. No protests were made over the American claim on Key West, so the Florida Keys became the property of the United States.


1823, Commodore David Porter of the United States Navy West Indies Anti-Pirate Squadron took charge of Key West, which he ruled as a military dictator under martial law. Porter was tasked by the American Navy to end acts of piracy in the Key West area including slave ships.


1830 Key West was the richest city per capita in the United States.


1845 Fort Zachary Taylor was active during the Civil War, contains the largest collection of Civil War cannons ever discovered at a single location.


1830 to 1861, Key West was a major center of U.S. salt production, harvesting the commodity from the sea by using the receding tidal pools. After the outbreak of the Civil War, Union troops shut down the salt industry after Confederate sympathizers smuggled the product into the South. Salt production resumed at the end of the war, but the industry was destroyed by an 1876 hurricane and never recovered.


1860 The Ten Years' War, the Cuban’s unsuccessful war for independence brought many Cubans that sought refuge in Key West.


1886 A large fire that started at a coffee shop next to the San Carlos Institute and spread out of control, destroyed 18 cigar factories and 614 houses.


1889,\ Key West was the largest and wealthiest city in Florida.


1898 USS Maine was a United States Navy ship that sank in Havana Harbor contributing to the outbreak of the Spanish–American War in April. American newspapers, engaging in yellow journalism to boost circulation, claimed that the Spanish were responsible for the ship's destruction. Crewmen from the ship are buried in Key West, and the Navy investigation into the blast occurred at the Key West Customs House.


1912 Key West was connected to the Florida mainland via the Overseas Railway extension of Henry M. Flagler's Florida East Coast Railway.


1926 Pan American Airlines was founded in Key West, originally to fly visitors to Havana. The airline contracted with the United States Postal Service to deliver mail to and from Cuba and the United States. The mail route was known as the Key West, Florida – Havana Mail Route.


1935 The Labor Day Hurricane destroyed much of the railroad and killed hundreds of residents, including around 400 World War I veterans who were living in camps and working on federal road and mosquito-control projects in the Middle Keys. The FEC could not afford to restore the railroad.


1938 The U.S. government rebuilt the rail route as an automobile highway and was built atop many of the footings of the railroad. It became an extension of U.S. Route 1. The portion of U.S. 1 through the Keys is called the Overseas Highway.


1928 Hemingway came to Key West, just passing through, not intending to stay. He lived in Key West, off and on, for approximately 11 years. He wrote six books in Key West. A Farewell To Arms, Death In The Afternoon, Winner Take Nothing, Green Hills of Africa, To Have and Have Not, and The Fifth Column and the First Forty-nine.


1959 Prior to the Cuban revolution there were regular ferry and airplane services between Key West and Havana.


1961 John F. Kennedy was to use "90 miles from Cuba" extensively in his speeches against Fidel Castro. Kennedy himself visited Key West a month after the resolution of the Cuban Missile Crisis.


1970 Key West came into its own as an offbeat destination for people who wanted to live by their own rules.

1971 Jimmy Buffett arrived and the island has been associated with his famous song Margaritaville ever since.


1979, Key West experienced its first Fantasy Fest. The 10-day bacchanal at the end of October is now a legendary annual tradition.


1982 The city of Key West briefly asserted independence as the Conch Republic as a protest over a United States Border Patrol blockade. This blockade was set up on US 1, where the northern end of the Overseas Highway meets the mainland at Florida City, in response to the Mariel Boatlift. A traffic jam of 17 miles ensued while the Border Patrol stopped every car leaving the Keys, supposedly searching for illegal immigrants attempting to enter the mainland United States. This paralyzed the Florida Keys, which rely heavily on the tourism industry.


The Conch Republic declared that is the world’s first “fifth world” nation: “We exist as a ‘State of Mind,’ and aspire only to bring more Warmth, Humor and Respect to a planet we find in sore need of all three.” The Conch Republic slogan is "We Seceded Where Others Failed" and all Key West residents are dual citizens of both the United States and the Conch Republic.




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