Scandalous History Facts about Key West
If you love slow travel, culture, AND THE WACKY, you’re gonna fall in love with a place like the Conch Republic, called initially "Bone Island or Cayo Hueso." Key West goes way back, long before Matthew Perry planted the U.S. flag in 1822. It is brimming with history, tourists, and eccentricities (there's even an entire haunted side - only for the brave souls). In fact, The Old Town is famous for its graceful colonial homes and its long Duval Street, a more topical version of New Orleans Bourbon Street with tons of eateries, markets, and bars to be entertained, but also for the unsolved mysteries.
For true history hunters, there's a rich background full of quirky facts that won't surprise most Conchs, but might raise some eyebrows from our visitors. As Mayor Tony Tarracino said, "Key West is an insane asylum. We're just too lazy to put up the walls or fences."
Let's dive in.
Bizarre Facts you Didn't Know About Ernest Hemingway
Starting this time capsule with a beloved character makes every visitor who puts a foot on this island fall in love with literature: The illustrious Ernest Hemingway. One of the foremost writers of the 20th century.
But first, a quick bio overview: Born in 1899, in 1918 enlisted in the army, became a soldier and a hero in the same year. Moved from Cuba to Key West in 1938, worked with the feds, followed by the FBI until he committed suicide. And last but not least, of course, wrote almost half of his major works from his mansion near the Key West lighthouse, both of which can be toured. The Home and the Museum were initially built in 1851 and restored by the Hemingways in the 1930s. It is still considered a National Historic Landmark for all to appreciate. Yes, we all know these facts, but did you know that…
#1 It's quite possible that his most significant works were mysteriously stolen: In December 1922, Hadley Richardson (his first wife) boarded a train to Switzerland to meet Hemingway while working on a particular assignment. She had a pile of his unpublished manuscripts with her. She left her luggage when she went to get some water and when she returned, the case was gone, and all of Hemingway's writings vanished with it... He even offered a reward for their return, but they were never returned. In his memoir, A Moveable Feast, published posthumously in 1964, Hemingway wrote about the unfortunate event of his stolen works. Some people say that maybe it sits with a long lost treasure… Ummm, who knows…
#2 He once stole a urinal from his favorite bar: After deciding that he had "pissed away" enough money in his favorite bar, Sloppy Joe's, Hemingway decided it was time to steal the urinal and displayed it in his home in Key West. Afterward, he converted it into a garden fountain (very creative of him), and now it's still on display for you to take a sneak peek on the grounds of his museum. Now all the six toed cats drink water from it. Don't miss it on your next visit ;) But please don't pee in it!
#3 A failed KGB spy: Yes, ladies and gentlemen, the FBI had a 125-page file on him. Nobody knew the truth, at least for quite some time, not even A.E. Hotchner (one of his closest friends, he wrote a biography titled "Papa Hemingway") nor Hemingway's wife (his 4th wife btw, not that we're counting). It wasn't until 1983 when a professor at the University of Colorado named Jeffrey Myers filed a "Freedom of Information" request from the United States government so they could finally release their file on Ernest Hemingway. Who knows what his motivation was to make that request?
The file, unsurprisingly, starts in the early 1940s, when Hemingway worked for the FBI. But it goes on for over 120 pages (15 pages of which are redacted) and continues into the 1950s and 1960s. As it turns out, Hemingway was being watched by the FBI all the way up to when he was admitted into the Mayo Clinic…
There are several assumptions about how the story ends for our short-story writer, but one thing is sure: he survived numerous diseases, and two consecutive plane crashes but could not save himself.
As he once declared "Every man's life ends the same way. Only the details of how he lived and died distinguishes one man from another."
"Where is 'Bum' Farto"?
A legendary Key West fire chief, Joseph "Bum" Farto (yes, it's his real last name), disappeared mysteriously in 1976 while awaiting sentencing for drug trafficking and became known as the Jimmy Hoffa of Key West.
His conviction stemmed from Operation Conch – a sting operation that found Farto allegedly selling cocaine from the city's fire station. The island has swirled with rumors of his fate since he disappeared.
Some locals believe he escaped to Central America, while others believe he was kidnapped and killed by members of a drug cartel. Jimmy Buffett sang about his disappearance and helped popularize the question, "Where is Bum Farto?".
While no one knows for sure, his desk, cigar ashtray, telephone, top hat, and uniforms are all on display at the Key West Firehouse Museum. Some people believe his ghost also resides inside. Also, in case you didn't know, the building where he grew up has been known as Sloppy Joe's Bar ever since. What a small island, don’t you think?
What was buried in Key West in 1972?
No, not the wacky epitaphs this time. Once upon a time, back in 1972, when the island marked its 150th birthday, locals put together a time capsule filled with personal mementos, books, and letters from residents. The plan was to open it 50 years later — March 2022.
While planning Key West's 200th birthday as a settlement in March 2022, people began talking about the old time capsule — nobody knows where it is.
Paul Menta, the chair of the committee for the celebrations, started hearing questions about it — from when the island celebrated its 150th birthday in 1972 — "They were just like, 'Mmm ah — do you know where it is?'" Menta said. "And I was like, 'No!'". Newspaper stories from the time described it as going into a new development called Old Town Square. Fifty years later, there's no such place. Menta went looking in the area the stories described.
"Nobody remembers where it is, that's the thing," said Alex Vega, 69, the first to bring up the missing time capsule. Vega knows his history. A retired thirty-year veteran firefighter, and his family, have lived more than a century in Key West. He's president of the nonprofit Old Firehouse Preservation, which runs the Key West Firehouse Museum. "They can't find it in 50 years, much less another hundred,"
Let's just say that we wish we were as good at saving our money as Key West at hiding their treasures. The exciting part here is that according to the citizen stories from 1972, it's got letters from President Richard Nixon, Governor Reubin Askew, Congressman Dante Fascell, and the editors of South Florida newspapers, written to their counterparts when Key West celebrates its tricentennial. That will be in March 2122.
The bottom line is that Key West people expect the bicentennial time capsule for 2072, which resembles a monument, won't disappear. Even four local children — ages 9 to 12 — were named ambassadors of Key West to be present when it opened and share their stories of growing up on the island.
"That's why I put mine above ground," Menta said of the new time capsule. "We sealed everything. The worst thing is that you'll need a snorkel mask to see it."
Not Historical But Needed: Key West Has The Most Bartenders Per Capita Than Anywhere Else!
You heard right. If you need a cocktail or a cold beer for the spirit, Key West is officially the place to be. The Southernmost City has the highest concentration of bartenders in the nation, 13.3 per 1,000 residents and counting!
Now that you've seen some of the quirky sides, we hope you're ready to dive into the relaxing options around The Keys.
Oh, and don't forget, the infamous characters await. Book your free travel plan, some ghost tours & enjoy the wacky side of The Keys.