Hey there, island dreamers! How about we dive into some quirky, must-know trivia about our beloved Key West?
Why? Because there’s nothing better than wowing your friends at the next pub trivia night — especially when you’re the one who seems to have all the answers.
So grab a drink, kick back, and let’s dive into some fun Key West facts you might not know… yet.
Key West Trivia to Sip & Share
- Southernmost bragging rights – Key West is the southernmost point in the continental U.S. Just 90 miles from Cuba! And yes, that iconic buoy is the place to prove it.
- Shipwreck riches – Back in the mid-1800s, Key West was the richest city per capita in the U.S., thanks to its booming shipwreck salvage industry (aka “wrecking”). Talk about treasure hunting!
- Hemingway’s home… and his cats – Ernest Hemingway lived here for nearly a decade. His house is now a museum, and it’s home to about 60 six-toed cats (descendants of Hemingway’s own cat, Snowball).
- The Conch Republic rebellion – Did you know Key West seceded from the U.S. (briefly) in 1982 and declared itself the Conch Republic? It was a cheeky protest against a border patrol roadblock. Of course, the “country” immediately requested foreign aid. Classic Key West humor!
- Truman’s island getaway – President Harry Truman spent 175 days of his presidency at his Little White House here. Presidential vacation goals, right?
- The reef life – Key West is home to the largest coral barrier reef in North America (part of the Florida Reef), and it’s the third largest in the world. No wonder it’s a snorkeler’s paradise.
- Cemetery giggles – The Key West Cemetery has some hilarious gravestones. One famously reads, “I told you I was sick.” Dark humor at its best.
- Sloppy Joe’s switcheroo – The original Sloppy Joe’s wasn’t where it is today. After a rent dispute in 1937, they moved the entire bar overnight. Now that’s commitment!
- Closer to Cuba than Miami – Yep, Key West is closer to Havana than it is to Miami… and definitely closer than the nearest Walmart!
- Margaritaville magic – Jimmy Buffett wrote his iconic song Margaritaville while living (or at least heavily inspired by) Key West. Grab a margarita and soak in the vibes.
- Duval Street’s fame – Duval Street runs from the Gulf of Mexico to the Atlantic Ocean. Some call it the longest street in the world, but it’s about a mile and a quarter. Though after a late night out, it might feel like five miles!
- Hemingway lookalikes everywhere – Every July, Hemingway Days take over the island, complete with the world-famous Hemingway lookalike contest at Sloppy Joe’s. Get your beard ready.
- One Human Family – Key West’s official motto is “One Human Family,” embracing diversity and acceptance. Just one more reason to love this island.
- A flat island – The highest natural point on Key West? Only 18 feet above sea level (at the cemetery, funnily enough). Yep, it’s as flat as a pancake.
- A bony history – The island’s original Spanish name was Cayo Hueso, or “Bone Key,” thanks to the bones reportedly found from Native American burial grounds. Spooky!
Bonus Facts to Really Flex at Trivia
- Key West was Florida’s largest city in the 1830s and 1840s!
- The first international flight from Key West in 1927 went straight to Havana, courtesy of Pan Am.
- The actual southernmost point is technically on the nearby Navy base (but you can’t get in there).
- Tennessee Williams finished writing A Streetcar Named Desire while living in Key West. (Rumor says at La Concha Hotel.)
- Wild chickens roam free all over the island – descendants of birds brought by early settlers and Cuban immigrants.
- Frost? Never heard of her. Key West has never recorded frost. Coldest temp? A cool 41°F. Shorts weather, right?
Treasure Hunters & Ghost Stories
- Mel Fisher found treasure worth hundreds of millions from the Spanish galleon Nuestra Señora de Atocha near Key West in 1985, and the hunt still continues today.
- The Key West Lighthouse was operated by a female keeper in 1848 – pretty groundbreaking stuff!
- During WWII, Key West served as a major submarine base. You can still spot remnants today.
- Robert the Doll at East Martello isn’t the inspiration for Chucky (sorry horror fans), but he does have his own creepy legend.
Take Your Trivia to the Tiki Bar
Now you’re officially armed with some serious Key West trivia gold. Bring these to your next pub trivia night or even your backyard tiki bar gathering. Just don’t tell your friends you had a cheat sheet, okay?
And if you want even more fun:
- Where to drink (hello happy hour!)
- Where to eat (yum!)
- What to do (so much!)
- Plus, our always-updated events calendar.
Oh! And don’t forget to join our Fun in Key West Book Club – all the books are either set in or inspired by the Keys, and we’re having a blast over there.
