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As you know, I absolutely love visiting Key West! I’m happiest when soaking in the city’s tropical vibes, listening to Jimmy Buffett songs, and feeling the stress melt beneath the country’s southernmost sunset. Key West has a special place in many people’s hearts as a city for misfits, a place for big dreamers who want solitude and freedom. But how did it come to be? Let’s dive into the history of Key West, Florida.
The History Of Key West
The city has a wild history filled with stories of adventure, mystery, and comedy. Key West’s history has made it one of the world’s most famous island tourist destinations, and its colorful people continue the long tradition of fun in the sun.
As they say, Key West isn’t so much a place as a mindset.
Historical & Fun Facts About Key West
In this post, I want to highlight some of the more fascinating facts about the history of Key West. I’m touching on lesser-known facts you may not already know. Trust me, there are a lot of them hidden in this eccentric paradise!
And knowing all of these great tropical tidbits of information will ensure you appreciate this charming community on your next trip!
Key West Was Originally Called “Bone Island”
An obscure fact about Key West is that centuries ago, it was called “Bone Island.” The ancient fishermen visiting the island found large amounts of human remains there. It turns out that ancient indigenous peoples used the island as a communal burial site.
The Island Was Sold Twice
It’s true! In 1790, Spaniard Don Juan de Estrada received the island through a land grant from the Spanish government. He then sold it to Juan Pablo Salas in 1815.
Salas was so excited to make a profit on the island that he sold it twice! First, to John Simonton, for $2,000 in 1821. And second, in 1822, to an attorney named John Strong. It took many years for ownership to get straightened out, and Simonton was declared the rightful owner in 1828.
Only One Of Key West’s Founding Fathers Lived There
Of the four founding fathers heralded as the original settlers and developers of the city, only one spent a significant amount of time living there. Pardon C. Green lived permanently on the island in the early and mid-19th century. While in Key West, he started a company, was a city council member, and briefly served as mayor.
Key West Is One Of The Warmest Places in The Country
Key West, Florida, is the southernmost point in the United States. You can see a famous bright red buoy marking this point at the corner of South and Whitehead Streets.
It’s one of the sunniest and warmest places in the US, with 260 annual sunny days and temps ranging from 65°F to 89°F. Key West also has the warmest ocean water of any place in the United States in the winter and averages 75°F to 77°F.
Key West Is Near A Giant Barrier Reef
Key West sits on the only living coral barrier reef in the US. Several related reefs extend 350 miles from the Dry Tortugas west of Key West to the St. Lucie Inlet near Miami. Coral reefs are home to many marine life and a unique underwater ecology. Almost 1,400 species of aquatic plants and animals live in the Florida Reef.
Key West Is Closer to Havana than Miami
Key West is closer to Havan, the capital of Cuba, than Miami, Florida. Key West is so far south in Florida that it’s very close to Cuba, which lies only 95 miles off-shore. Due to their proximity, Key West and Cuba often share common elements of their culture, people, and economy.
Ernest Hemingway Loved Key West
The Nobel Prize-winning author Ernest Hemingway lived on the island during the middle of the 20th century. You can still tour his home and see his amazing six-toed cats. They all descend from “Snow White,” a six-toed cat Hemingway received as a gift. The cats have a genetic mutation that gives some cats six or more toes! This trait is reliably passed down to each generation of newborn kitties.
At the Hemingway House, you can also see the penny he placed in the wet cement of his pool. It was the first pool built in a 100-mile radius and was so expensive he put the penny there and exclaimed, “You can take my last penny!’ when he saw the construction bill.
I love reading about the history of Key West as it relates to Hemingway!
A Lot Of Famous People Have Lived In Key West
For a small town with a population of only 26,000, Key West boasts an astounding number of famous inhabitants over the years. They all contributed to the history of Key West in one way or another!
A short list includes author Judy Blume, poet Wallace Stevens, author Shel Silverstein, playwright Tennessee Williams, President Harry S. Truman, author Earnest Hemingway, singer Jimmy Buffet, NASCAR Driver Dale Earnhardt Jr., poet Robert Frost, author Truman Capote, fashion designer Calvin Klein, and treasure hunter Mel Fisher.
Key Lime Pie Was Invented In Key West
Was Key Lime Pie first made in Key West? Legend has it that in the late 1800s, Key West sponge fishermen called “Hookers” would make homemade food by pouring sweetened condensed milk with lime juice over Cuban bread. Wives of these men began baking it into a pie crust to create a sweet dessert.
Sarah Jane Lowe Curry, the daughter-in-law (other legends say she was his cook) of Florida’s first millionaire, started serving the dish to people who came to her house. Sarah, or “Aunt Sally” as she was known, became the mother of the Key Lime Pie. Soon after, the pie was being served in restaurants everywhere.
Whether or not you believe these stories, the truth is that Key Lime Pie is a famous Key West dessert, and you can find these delicious pies served at many of the city’s restaurants.
Chickens Walk The Streets of Key West
Yes, Key West has a lot of chickens wandering around the city! Chickens are the original inhabitants of the keys. Early locals lived alongside them and raised them for eggs or meat.
The ancestors of these birds have become the official Key West Gypsy chickens, and they proudly and unabashedly prowl the streets of Key West. Seeing these fowl reminded me of Ybor City and their resident chickens!
In 2004, the city hired a professional bird catcher. But, the citizens did not receive it well, and the position was eventually eliminated. Now, you can enjoy the Gypsy chickens, and they get to live a peaceful life as a tourist attraction in one of the nation’s top vacation destinations!
Key West Is The Birthplace of Pan Am Airlines
Pan American Airlines started in Key West, Florida, in 1927. The location is now home to First Flight, a restaurant and bar. But the aviation history of Key West doesn’t stop there!
Known as The Amazing Race, in 1913, a competition started between two early aviators to see who could make the first flight from Key West to Havana, Cuba.
Then, in 1920, Aeromarine Airlines flew America’s first official international airmail service, once again between Key West and Havana.
President Truman Made A “Little White House” in Key West
In 1946, President Harry S. Truman began using a home in Key West as a winter retreat and operated it as a remote “White House .” He stayed in the home intermittently for 175 days over 11 visits. This house had earlier famous visitors, including President William Taft and Thomas Edison.
Today, the home is the Harry S. Truman Little White House. It’s Florida’s only presidential museum. At the museum, you can tour the home, see Presidential memorabilia and photos, and learn the history of Truman’s presidency and its importance to Key West. The house is set within a beautiful botanical garden filled with tropical flora.
I visited the museum, and I highly recommend it! Not only did we learn about President Truman while on the tour, but we also learned a great deal about the history of Key West.
Key West Loves To Celebrate
For a small island, Key West has a tremendous capacity to party! It’s known for several famous annual festivals that attract people from all over the world.
The Conch Republic Independence Celebration (April 20-29, 2024) starts with a conch-blowing contest. It continues with boat races, a parade on Duval St, victory pirates, and a Pirates Ball and Costume competition.
The Key West Songwriters Festival (May 1-5, 2024) showcases veteran and new songwriters who take the stage to mesmerize audiences with music and storytelling. Household names like Kacey Musgraves and Florida Georgia Line got their start here.
Hemingway Days (July 17-20, 2024) honors the giant legacy of author Ernest Hemingway by doing something he did best: celebrating. The festival includes presentations by Hemingway scholars, appearances by Hemighway family members, and an awesome look-a-like contest where hundreds of white-bearded, swarthy men channel their inner “Papa.”
Fantasy Fest (October 18-27, 2024), which started as a costumed parade down Duval Street, has grown into 10 days of parades, parties, street fairs, and fantastical balls. Most of these activities are not for kids. Adults might have fun at the “naughty” bike rides, pajama parties, and burlesque shows across the city. So, if you are visiting Key West with kids, avoid that week!
Key West Has Many Famous Buildings
Key West is filled with buildings with an intriguing history. Aside from the more popular places like the Hemingway House and the Truman Little White House, several other famous buildings exist.
The Audubon Hosue and Tropical Gardens showcases works from the ornithologist John James Audobon. Audubon drew 18 new birds after having visited Key West. You can explore the house and its 1-acre surrounding gardens.
The Basilica of St. Mary Star of the Sea is Florida’s second oldest Catholic parish, founded in 1846. Pope Benedict XVI raised the church to a minor basilica in 2012. You can enter the basilica and take a self-guided tour.
The Mel Fisher Maritime Museum contains an extensive collection of treasures and artifacts from 17th-century shipwrecks. The museum highlights the discoveries of treasure seeker Mel Fisher and his contributions to maritime archeology. Here, you can see Spanish gold coins, learn about the real pirates of the Caribbean, and explore the science of shipwrecks. Tickets are required. This is one of my top recommendations for families who want to learn more about the pirate history of Key West.
Key West Is Known As The Conch Republic
Did you know Key West once seceded from the US and became its own country?
In 1982, out of frustration over a border checkpoint that stopped most traffic into and out of the keys, Key West sarcastically notified the Federal government they were seceding from the Union. They gave their new country the name “Conch Republic.”
This name has become a unifying moniker for the people of the Keys and a rallying cry for citizens who value freedom and independence. You’ll see the name all over. Even the Key West high school got the fever, naming their mascot the “Fighting Conch.”
I laughed when I saw the Conch Republic’s official flag, which bears the motto “We Succeeded Where Others Failed.”
Key West Is Home To The Oldest Bar in Florida, or Is It?
Caption Tony’s is an iconic bar located just a block off Duval Street and was actually the original home of Sloppy Joe’s Bar. The sign out front says it’s the oldest bar in Florida. However, other sources say that the The Palace Saloon on Amelia Island is the oldest bar in Florida. I will have to pop in and ask them about it when I visit next month!
Did you know that Jimmy Buffett played Captain Tony’s in the early 1970s?
Key West Is A Fisherman’s Paradise
Anglers in the Keys have caught some of the largest fish on record in Florida. These include a 240-pound Yellowfin Tuna, a 243-pound Tarpon, a 612-pound Swordfish, and a 686-pound Great White Shark.
Key West has a legendary reputation for fishing. Initially made famous by the stories of Hemingway, the coral reefs and deep blue waters of the Florida Straits are well-known for their massive catches.
Fishing here is diverse, and many different fish are regularly biting. Tarpons are heavyweight champions and can top 200 pounds. Bonefish are called “Grey Ghosts”; they are smaller but harder to find. Snapper and Grouper can be caught year-round and are sought after for their great taste. They like patch reefs, wrecks, and bridges and can even be caught from shore. If you want to go farther from shore, Blackfin Tuna are wonderful to eat and very plentiful in the spring. Sailfish, Swordfish, and Marlin are the kings of the sea and will give you the fight of your life.
These majestic giants drew Hemingway here and continue to thrill sport fishers with their strength and size. The warm waters off the coast bring in smaller Blacktip and Bonnethead sharks. Or you can pit yourself against apex predators like the giant Bull, Tiger, and Hammerhead sharks.
Key West Was Once The Cigar Capital Of The US
Many people don’t know Key West was the original epicenter of the Cuban cigar industry in America.
The first cigar factory started here in 1831, and by 1890, there were at least 80 factories in Key West. The factories were tightly connected to Cuba and would import Cuban tobacco leaves to be hand-rolled by Cuban emigres in Key West factories. The legendary Arturo Fuente began rolling here in 1912.
After hurricanes hit Key West, destroying some factories, and local unrest around labor unionization, most factories moved to Ybor City in Tampa. Several small factories still operate in Key West, like the Key West Cigar Factory, Rodriguez Cigars, and the Island Cigar Factory.
Jimmy Buffett Got His Start In Key West
The iconic singer and songwriter Jimmy Buffett moved to Key West in 1972. After having no success in the Nashville record business, he decided to take a trip with a friend to the Keys for some needed relaxation.
He ended up living in Key West for seven years, working various odd jobs and singing in the local dives and honk-tonks. The island ambiance of the Keys inspired his casual style and tropical-themed lyrics. His hugely popular songs like Margaritaville became synonymous with Key West, and enjoying the salt and sea lifestyle became a popular pastime for fans worldwide.
I read some amazing stories about Jimmy’s time in the 1970s in Key West. He became part of a “Rat Pack” of close friends, many of whom were aspiring authors and poets, all following the spiritual footsteps of Hemingway. Stories of epic week-long deep sea fishing trips, hard partying, and great friendship make this era of his life reminiscent of the “Lost Generation” of Paris ex-pats in the 1920s.
A book I love that focuses on Jimmy and his rat pack in the 1970s is titled Mile Marker Zero: The Moveable Feast of Key West. And if you haven’t read A Pirate Looks At Fifty, you must!
The Rum Runner Drink Was Invented Near Key West
Legend has it that the famous Rum Runner cocktail was invented in 1972 at the Holiday Tiki bar in Islamorada, near Key West.
In one story, bartender John Ebert was challenged by the Holiday Tiki Bar owner to use up a lot of unused liquor that hadn’t been drunk (called “dead stock”). John mixed the ingredients in a new way to make the first Rum Runner.
In another version of the story, John was looking for a job, and the owner of the Tiki Bar asked him as part of the interview to make a delicious drink with lesser-known ingredients.
Either way, we now have the tasty Rum Runner – a sweet libation that has slaked the thirst of many a beach bum and tropical reveler around the globe.
Booking.comEnjoy The History Of Key West On Your Next Trip
Key West history is filled with fascinating stories of larger-than-life personalities, rising and falling fortunes, boom and bust industries, and enduring people committed to life by the sea. Their stories are diverse, but they are all driven by fierce independence and a yearning for freedom away from society. The fun thing about the history of Key West is that there are always new tales to listen to on every visit!
Key West is one of my favorite places to visit because of its charming eccentricity and its desire to be true to itself. It’s a fantastic place to relax, try new things, and enjoy the “Salt Life.” When planning your trip to the Conch Republic, be sure to set aside time to see some of the historical places. Catch the setting sun and sip a Rum Runner while you marvel at all this city offers.
And if you are looking for things to do in Key West, I have got you covered with several great Key West travel blog posts!
18+ Things For Families to Do in Key West
Riding the Iconic Conch Train Tour in Key West
All About the 6-toed Hemingway House Cats
My Momcation at the Marker Key West
Visiting the Truman Little White House
Snorkeling & Sunset Tours with Sebago Watersports
The Key West Hop-On Hop-Off Old Town Trolley Tour
PIN: History of Key West, FL
