What To Do in Key West

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 where riddled with STDs and became an episode of Bob’s Burgers – swinger scene.

In this guide

1. Watch the sunset at Mallory Square: And get heckled by a guy in a kilt on a unicycle
2. Take a Hemingway House tour: Greet the polydactyl overlords
3. Visit the southernmost point: But immediately leave because it’s a mob scene
4. Drink a Rum Runner at Sloppy Joe’s: And then slowly question your life choices
5. Take a ghost tour: Meet the guide who swears he dated a phantom
6. Rent a bike: Surrender to the island’s labyrinth
7. Grab Cuban coffee and a guava pastry at 5 Brothers
8. Visit Fort Zachary Taylor: Bring a swimsuit and a paranormal detector
9. Take a day trip to Dry Tortugas National Park
10. Just sit, drink, stare at the horizon, repeat

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?”

The intoxicating lure of Key West

This is the town’s mantra, one that is inspired by pirate logic with sunscreen and very loose leash laws. But in the nose of all that chaos, there’s a hidden poetry. There’s an intoxicating rhythm of roosters, Bacardi and things that go bump in the humid drag queen night.

When done right, Key West seduces you, swallows you whole and spits you back out in flip-flops and fishnet. So now that we’ve warned you – in a previous article – what not to do in Key West (shoutout again to our friends the feral roosters and cursed dolls), let’s talk about what you absolutely should do if you want to tap into the real weird-beauty of the end of the American road.

So, let’s get lost, shall we?

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.

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.

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. You certainly should see it. But then you should flee. Treat it like a sacred relic and a live grenade: touch, click, bounce.

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.” Every day. So, trust me, if the bar was opened during Hemingway’s lifetime in Key West, he drank there.

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. Go with it. Embrace it. If a guide starts crying mid-tour because the “wall got cold,” just nod and ask where the nearest drink shack is.

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. You’ll pass Victorian mansions, conch-style bungalows, actual people disguised as zombie parades (seasonal) and possibly a drag queen race. The air smells like salt, sunscreen and Malibu.

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. For the full lineup of where locals actually eat, check out the best restaurants in Key West.

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. Either as a recipe of “Aunt Sally” or as an offshoot of sponge fishermen that used the key lime stop to fight off scurvy and later incorporated them into drinks and sweet desserts.

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. You can tour the 19th-century brick fortress, hear tales of buried armories and Confederate conspiracies and then take ten steps and end up tanning on crushed coral. You might spot a pelican, a ghost and a minor TikTok star all within 30 seconds. No promises on the order.

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. If a full day out there feels like too much, here’s how to spend one day in Key West instead.

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. The man was Doctor Samuel Mudd. He is also one of the few that got a paroled. Why? He played a vital role in treating a yellow fever outbreak in that very prison.

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.

Frequently Asked Questions

What should you not miss in Key West?

Three things — the Mallory Square sunset (even if it’s ridiculous), a ghost tour with a guide who’s clearly seen something, and at least one afternoon at Fort Zachary Taylor’s beach. Everything else is a bonus.

How many days do you need in Key West?

Two days minimum to see the island without rushing. Three if you want a Dry Tortugas trip in there. Less than two and you’re just doing a tour in sandals.

Is Key West worth visiting?

If you want a manicured Caribbean experience, no. If you want a place that still feels a little bit weird and ungovernable, absolutely. Figure out which kind of traveler you are first.

What’s the best time to visit Key West?

December through April for weather. Late September through mid-November for lower prices and thinner crowds. Avoid hurricane peak (August–September) and spring break (March). For the full breakdown, see the worst times to visit Key West.

Let your freak flag fly

Here’s the thing about the Keys and the locals will verify – here it’s a live and let live type of mindset. Folks don’t really care how weird, how outlandish, how bat guano insane you are, as long as you don’t pry or mess with their groove.

You can be and do whatever you want as long as “you don’t put your feet up on my coffee table. This is why, at its heart, Key West isn’t a checklist. It’s a frequency. You tune in or you don’t.

You’ll hear it. The hum of a jet ski somewhere off the coast, headed for Cuba, chased by Coast Guard warnings and the echo of a town that refuses to be normal.

What is your best advice for what to do in The Keys? Let us know in the comments!