The Best Things To Do While in the Conch Republic
We begin, as all things in Florida do, with someone on a jet ski headed for Cuba.
It was 2006. Not the year Britney shaved her head (that was later) and not the year Florida accidentally elected an iguana as HOA president (true). And not the year “Dateline” did an investigation into Florida senior communities – and discovered the places were riddled with STDs and became an episode of Bob’s Burgers – swinger scene.
It was the year Key West mayoral candidate and local stuntman (titles often overlap down here) Rocky Thompson strapped on a life jacket, hopped on a Sea-Doo, and tried to jet ski to Havana. You read that right. It was an official event. The government big wig stood at the southernmost point, stared at the sea like a man possessed by too many Woodstock aftershocks, and declared:
“I’m taking this baby to Castro’s backyard.”
Did it work? Of course not. The U.S. Coast Guard intercepted him 20 miles out. There was also a guy who was rescued when he tried to reach the Bahamas in an inflatable hamster ball, unrelated to Rocky.
So, Rocky claimed it was a publicity stunt for tourism. The federal government called it “a bad idea with a fuel leak.” Key West locals? They shrugged and said, “Well, he’s no weirder than the guy who sells conch shells in a thong and calls himself Admiral Dave. Plus, remember Captain Tony?”
That’s the thing about Key West. This mad, coral-encrusted fever dream at the bottom of America doesn’t just tolerate chaos – it employs it. It gives it a business license, a cocktail and a spot on the sunset cruise. And when done right, it will seduce you, swallow you whole and spit you back out in flip-flops and fishnet.
Now – if you’re reading this, you’re probably doing one of two things. Either you’re going to Key West and need to know what to do when you get there. Or you’re sitting on a couch somewhere daydreaming about quitting your job, buying a one-way ticket and becoming “the guy with the hammock and the suspiciously excellent tan.”
Either way, you’re going to need a plan. And a place to stay.
But first – where are you crashing?
Here’s the thing most first-timers get wrong about Key West: they think it’s one vibe. It’s not. It’s at least three different islands pretending to be one, each with its own personality, price tag and blood alcohol level.
Old Town – is where the action is. Duval Street, the ghost tours, Hemingway’s cats, the sunset at Mallory Square – it’s all here. Hotels range from charming Victorian bed-and-breakfasts that smell like key lime and cigar smoke to boutique spots where the concierge is a guy named Tito who knows every bartender by first name and every ghost by last. If you want to stumble home from Sloppy Joe’s at midnight without calling an Uber, this is your zone. It’s pricier, sure. But you’re paying for proximity to the madness. See hotels in Old Town Key West
New Town – is where the locals live and the prices drop. You’ll find chain hotels, actual grocery stores and the kind of quiet that makes you forget you’re on a 4-mile-wide island that once declared war on the United States (they lost, but also kind of won – look up the Conch Republic). It’s a 10-minute bike ride to Duval. The trade-off is real: save $100 a night, pedal 10 minutes. For some folks, that’s a no-brainer. See hotels in New Town Key West
Stock Island – is the wildcard. It’s technically the island next door, connected by a bridge. This is where the shrimp boats dock, the artists hide and the Airbnbs have actual character. If you want to feel like a local and don’t mind being a short drive from the tourist scrum, Stock Island is your move. Also, there’s a bar here with a pig. Not a metaphor. See stays on Stock Island
Got your base sorted? Good. Now let’s talk about what you’re actually going to do in this beautiful, sunburned asylum.
What to do in Key West
Let’s ride, compadre. We’re dropping into the bottom tip of the continental U.S., where the sun burns a little brighter, the laws blur around the edges, and the most rational decision you’ll make all day is to buy a $9 mojito from a man dressed like a Victorian ghost pirate with a very pronounced Russian accent and what could only be described as the odor of “Au de High Life” doing cartwheels around his very soul.
1. Watch the sunset at Mallory Square: And get heckled by a guy in a kilt on a unicycle
This is called the Sunset Celebration. If you went to Key West and missed out on it, well, you didn’t go to Key West. You don’t go to Mallory Square just to watch the sunset.
No, you go to let the circus happen to you. Fire jugglers. Sword swallowers. Conch shell musicians playing the national anthem. A tightrope-walking cat troupe (AGAIN, this happens)
Of course, it’s a tourist trap. But it’s the type you actually want to get ensured in. It’s like the Grand Canyon, “Dude it’s just a hole in the ground… massive tourist trap”.
The sun setting into the Gulf is just the excuse. The real show is the locals who’ve been perfecting their weirdness for decades. And remember: tipping the guy who juggled machetes while screaming about property taxes is not just courteous, it’s a survival trait.
And yes, that’s really is a bar, made out of wooden barrels floating in the surf, with inflatable stools and a guy driving it around with a leaf blower.
Pro tip: Hotels near Mallory Square in Old Town put you within walking distance. You’ll want to be close because the celebration starts at golden hour and the walk back after three Rum Runners is… educational. Find hotels near Mallory Square
2. Take a Hemingway House tour: Greet the polydactyl overlords
Yes, Ernest Hemingway lived here. Yes, he wrote here. But let’s get one thing straight: the real rulers of this house are the 60+ six-toed cats descended from Papa’s own feline sidekick.
These cats roam the Spanish colonial estate like they’re on salary and they are, in a way, cause the Chamber of Commerce actually has them on their yearly budget, providing for their food and welfare.
They sleep where they want and pose for your photos. Honestly, they are more respected than some Florida residents. The house itself is a literary temple, sure – but the cats? The cats are the content.
And speaking of things you should know before you go – we wrote a whole piece on what NOT to do while you’re down here. Trust us, you’ll want to read it before you accidentally try to pet a rooster or drive down Duval.
Read: What NOT to do in Key West (seriously, read this first)
3. Visit the southernmost point: But immediately leave because it’s a mob scene
Here’s the thing: it’s iconic, yes. But it’s also a fight club disguised as a photo op. And the first rule of this Fight Club?
You don’t talk about the 5 year old who shouted obscenities reserved for prison inmates because “you cut into her photo opt.”
That concrete buoy – which technically isn’t even the real southernmost point (shoutout to Ballast Key, 10 miles farther south) is swarmed at all hours by selfie battalions.
4. Drink a Rum Runner at Sloppy Joe’s: And then slowly question your life choices
Sloppy Joe’s is where Hemingway allegedly drank, fought, brooded, and drank again. Today, it’s a boozy madhouse with live music, t-shirts, and bartenders who could talk down a Bengal tiger in spring heat.
The Rum Runner is the local rite of passage – part drink, part spiritual possession. You’ll wake up with three new friends, a half-finished novel on your Notes app and maybe a rooster feather in your pocket.
Also, here’s the thing – the first Sloppy Joe’s is about a few feet south, it’s called Captain Tony and Hemingway also drank there. Here’s another thing – Hemingway had a rule, “write 500 words and then celebrate with a daiquiri.”
While we’re on the subject of Hemingway’s haunts – we did a deep dive into Jimmy Buffett’s Key West, too. The man turned this speck of coral into a billion-dollar brand. Worth a read if you want to hit the actual spots.
Read: Jimmy Buffett in Key West – The Town, The Myth, The Margaritaville Messiah
5. Take a ghost tour: Meet the guide who swears he dated a phantom
Key West is haunted. Not just metaphorically, but like, haunted-haunted. Why? Well, two things. One, ghosts can’t travel over water – according to people who know these things. So, they are trapped.
Secondly, Key West’s real name is “CAYO HUESO” – which translates to Bone Key. Why? Cause when early Spanish settlers descended on the island they uncovered mountains, and by that we mean mountains, of bleached out human bones. The place was a communal burial ground for native tribes.
Ghosts of shipwreck victims, dead pirates, bootleggers, brothel madams and Civil War deserters and that’s just in the first bar you walk into. Captain Tony’s bar? There is a tree in the middle. It’s a hanging tree.
There’s a bar that has human remains in the stools. And another bar that was once the morgue.
The ghost tours here are immersive. You’ll hear tales of Robert the Doll (do not take his picture without permission unless you want night terrors). And you might even be dragged into a reenactment or two.
Curious about what other chaos you should plan around – or avoid? We broke down the worst times to visit Key West. Spoiler: they might actually be the best times.
Read: Worst Times To Visit Key West (and why that might be when you should go)
6. Rent a bike: Surrender to the island’s labyrinth
Don’t rent a car. That’s a sucker move. Key West was made for two things: feet and wheels that don’t go above 12 mph. Rent a cruiser and pedal your way through pastel chaos.
Pro tip: If you’re staying in New Town or Stock Island, a bike makes the commute to Old Town easy and scenic.
7. Grab Cuban coffee and a guava pastry at 5 Brothers
This tiny little shop is where locals go to re-caffeinate and get re-centered. The café con leche here is rocket fuel disguised as a morning beverage.
The guava pastries? Sugar bombs blessed by old abuelas who know things you don’t.
You’ll need the energy, because after this, someone’s probably going to ask if you want to go “snorkel a shipwreck with an ex-marine who owes me a favor.”
Also, the key lime pies – there’s some debate as to which bakery started to produce them, but there’s no they were spun in this place.
Speaking of expenses – Key West isn’t cheap. We broke down why everything costs what it does.
Read: Why Is Key West So Expensive?
8. Visit Fort Zachary Taylor: Bring a swimsuit and a paranormal detector
Historic? Yep. Haunted? Definitely. Good beach? One of the best in Key West.
However, given that Key West is mostly coral beaches, it’s not a great endorsement. The better beaches are one island over.
Fort Zach is like the weird lovechild of a Civil War documentary and a Jimmy Buffett song.
9. Take a day trip to Dry Tortugas National Park
You want adventure? Real adventure? Hop on a seaplane or ferry to Dry Tortugas, 70 miles west into open water. It’s a fortress-island with snorkeling that makes you believe there’s something real in the Bermuda Triangle thing.
You’ll see coral, cannons, sea turtles and maybe – just maybe – the part of yourself that still believes in pirates. But you’ll also burn in under 6 minutes if you forget sunscreen. Fair warning.
Also, this place is weird. Is it more weird than everything else? Yes. The fortress became a prison and for a time housed one of the people convicted of the conspiracy of the assassination of President Lincoln.
Pro tip: The Dry Tortugas ferry books up fast in high season. If you’re planning this, book your hotel AND the ferry at the same time. Seaplane is pricier but worth every cent for the views alone.
10. Just sit, drink, stare at the horizon, repeat
Look, at some point you’ll be full. Full of conch fritters. Definitely full of ghost stories. Full of sun, sweat, and whatever that drink was the guy in the flamingo suit made you try. That’s when you sit and grab a drink. You stare out at the sea. And you realize: this is the point of Key West.
The wild. The quiet. The convergence. You’re not here to do it all. You’re here to feel it flicker.
Plan your Key West trip
So there it is. Ten ways to lose your mind in the most beautiful way possible at the end of the American road. Whether you’re here for a long weekend or a slow week of doing absolutely nothing productive, Key West has a way of finding you exactly where you need to be.
The only question left: where are you staying?
| Article | Topic |
|---|---|
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What NOT To Do in Key West
Common sense goes to pass out in a hammock — roosters, cursed dolls and the Duval Street gauntlet.
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Tips |
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Worst Times To Visit Key West
And why those might actually be the best times. Fantasy Fest, hurricane season and shoulder-season secrets.
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Guide |
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Jimmy Buffett in Key West
The town, the myth, the Margaritaville messiah — every bar, studio and haunt the man made legendary.
|
History |
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The Best Restaurants in Key West
From Blue Heaven’s rooster-infested brunch to Garbo’s Korean BBQ tacos out of an Airstream.
|
Food |
|
The Real Story Behind the Conch Republic
Stale bread and the time the Navy surrendered to a guy on a paddleboard with a squirt gun.
|
History |
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Why Is Key West So Expensive?
A breakdown of where your money actually goes — and how to stretch it without sleeping in a hammock.
|
Budget |
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Key West’s Wildest Restaurant Backstories
Bars with human remains in the stools, a morgue turned saloon and Jimmy Buffett’s first gig.
|
Food |
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Best Things To Do in the Florida Keys
Beyond Key West — the full island chain from Key Largo to the Seven Mile Bridge.
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Guide |
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Best Things To Do With Kids in Key West
Family-friendly chaos — Hemingway’s cats, Butterfly Conservatory and Fort Zach beach days.
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Guide |