Key West’s Wildest Restaurant Backstories

Key West, where the food’s good, the ghosts are rowdy and history could be drunk

A couple of years ago, the manager at a Key West hotel looked up to find a group of men, with the dead eye of folks who have seen war, enter the lobby. They walked up to him decked in army camouflage and each one had an assault rifle. “Señor, we want El asilo…” Yup, there spies and comandantes from Fidel’s neck of the woods were there, asking for political asylum. Their raft had landed right next to the hotel’s tiki bar.

In this guide

1. Captain Tony’s Saloon
2. Blue Heaven
3. Sloppy Joe’s
4. Chart Room Bar
5. Green Parrot Bar

So, the hotel manager picked up the phone, called the local CIA station – and by local I mean the one down the street – and says, “We have another one… can you send someone over?” Did this happen? Yes, this is true.

And this is just one of the weird, often out of place, certainly out of whack, strange tales that pop up in Key West. An island that if you run in a complete circle around its shores, it is less than 16 miles.

This place has seen all the big names in piracy. All the great writers of the 20th century that had a knack for drinking like their liver could take on Superman with one arm tied behind its back. Spies and things? We’ve had missile launch pads on the beach next to sun tanning tourists.

This place was called Cayo Hueso… Why? Cause it was where the natives just dumped all their dead. The place was literally just bones, and buried treasure. So, when people started setting up shop, the vibe, the madness, the Bermuda Triangle pull of it started calling in more strangeness. It was akin to, I don’t know, going on vacation with John McClane… You somehow knew that proximity to the man would call in the chaos.

So, with that said.. Let’s talk about restaurant backstories. You want food? Yes, you’ll get it. You want flavor? Baby, this is Key West… the southernmost smorgasbord of America. But if you’re here just for the “culinary experience,” you’re missing the point. These are not just restaurants. These are relics. Characters. Madcap escapades wearing flip-flops and sporting a Mach ten in their G-String.

They’ve housed pirates, presidents, poets and enough people on a watchlist that the FBI’s motto might as well be, “Check Key West, then the Keys, then Miami and then Florida. And only then do we put up a wanted poster. “

Here are five Key West restaurants and bars with backstories wilder than a spring break confession booth.

The incredible backstories

1. Captain Tony’s Saloon

Located on 428 Greene St., Captain Tony’s is a former morgue, jail, telegraph station and hangout for misfits, miscreants and legends.

Let’s start with the King of Chaos. Captain Tony’s isn’t just a bar. It’s also a damn shrine to Key West’s boozy, brawling, bohemian soul.

This place was a morgue in the 1800s. Like, literally. There’s still a grave marker on the floor and, oddly, hanging from the ceiling. Hundreds of bras, license plates, business cards and the kind of debris that accumulates when you mix salt air with soul damage. In the middle, that tree? It was a hanging tree. When they caught a pirate, well, it’s self explanatory.

Jimmy Buffett played his first Key West gig here in the ’70s. Ernest Hemingway got liquored here before getting liquored somewhere else. And the Captain himself? Tony Tarracino. Bootlegger. Gunrunner. Smuggler. Four-time husband. One-time mayor. The man came to Key West after he woke up in a landfill up north being left for dead cause he had a disagreement with the mob. Tony came to the Keys and started making dough bringing “stuff” from “other places.”

His quote was “All you need in life is a tremendous sex drive and a great ego – brains don’t mean a shit.”

Yes, that’s on a T-shirt. No, it doesn’t come in medium. Yes, I have one… How did I get it? My wife went to the Keys and came back with the shirt: “It was the last size they had. I had to ask the bartender for it. He stripped it off and gave it to me as a favor. Then he asked if I wanted their specialty drink. He was Russian and had an eye patch.” My reaction? “Yup that’s pure Key West.”

You don’t come here for artisanal cocktails. In truth, you come here to drink something brown, question your choices, and maybe fall in love with a woman named Darlene who sells tarot cards out of her truck.

2. Blue Heaven

Blue Heaven is located at 729 Thomas St. It’s where roosters strut, pancakes are divine and the ghosts of Hemingway’s boxing matches hover over your eggs.

You sit down at a table in the middle of a dirt-floored tropical yard. Roosters are fighting for dominance next to your mimosa. A cat’s asleep under your chair. Bob Marley’s playing softly from a speaker mounted to a banyan tree.

Welcome to Blue Heaven, a place that feels like a Key West fever dream and it is. So, here’s the backstory: This place used to be a dance hall, and a bordello and a gambling den. But it was also the site of cockfighting and Ernest Hemingway sanctioned boxing matches. That’s right. Papa had a ring in the backyard. You could eat, drink, watch two guys pummel each other and get your palm read. Dinner and a show.

Today? The fights are gone (usually), but the soul’s intact. The pancakes are massive. The Key lime pie is aggressive. And you’ll leave believing in reincarnation, because that chicken eyeing your french toast? Might be Hemingway.

3. Sloppy Joe’s

Sloppy Joe’s is located at 201 Duval St. It’s where the drinks are cold, the history is sweaty and Hemingway once got in a fistfight with a urinal.

First off, yes, it’s touristy. Yes, of course, it’s loud, and yes there’s always some dude in cargo shorts yelling “Freebird!” at the band.

It’s in the air and also in the floorboards. Likely, It’s still in your bloodstream from the last time you came down here and blacked out with a bartender named “Cheeks.”

But what most folks don’t know is this: Sloppy Joe’s didn’t even start at this location. It began across the street, at what’s now Captain Tony’s. That was the original bar. And when the landlord raised the rent one sultry afternoon in 1937, the owner, a guy named Joe Russell (a Hemingway drinking buddy, rum-runner and the closest thing Key West had to a functioning adult at the time) said:

“Hell no.”

So they picked up the whole bar, I’m talking stools, pool tables and probably a half-conscious patron or two, and moved all of it across the street. Mid-shift. But that’s the kind of logistical madness that only happens in Florida or a Spike Jonze film.

Hemingway? Oh, he was there. He drank here regularly. Probably bled here too. Joe Russell was actually the inspiration for “Freddy” in “To Have and Have Not,” Hemingway’s Key West novel. That’s how close they were.

There’s also the annual Hemingway Look-Alike Contest, where 300 bearded men yell “Papa!” and flex their literary dad bods to be crowned king of the bar.

4. Chart Room Bar

Located at Pier House Resort, 1 Duval St, this place is where Jimmy Buffett ate bar peanuts and also signed a record deal while wearing flip-flops.

The Chart Room Bar isn’t just hidden, it’s half-spectral. Tucked inside the Pier House Resort, this little bar has more stories than a Hemingway short fiction anthology. And also, more human remains than most dive bars are legally allowed to admit. But they do have free hot dogs.

Let’s start with the big one: There are actual ashes of longtime patrons mixed into the bar and booths. Yes. Real ashes. In jars, in the wall. Probably on your stool. It’s practically a morgue with a rum budget.

This is where Jimmy Buffett got his start, singing for drinks and hanging out with locals who probably had more smuggling stories than working passports. Tom Corcoran (photographer and mystery writer), Hunter S. Thompson, even some old-school Shrimp Pirates, they all bellied up here.

There’s no music, no flash and absolutely no judgment. Just strong drinks, heavy ghosts, and the kind of quiet that only happens when the bartender doesn’t want your troubles and is packing a sawed off shotgun right where he can get it fast.

5. Green Parrot Bar

Located at 601 Whitehead St., this is the oldest bar in Key West. It is also the only one that feels like it remembers Prohibition, and maybe even caused it.

Okay, technically, it’s a bar. But come on – they serve peanuts and things in gallon jugs. You can eat here (depending on how you define “calories”), but you really drink and listen and live here.

The Green Parrot was originally a grocery store in 1890. Then it became a bar for Navy submariners. Then it became the unofficial Key West watering hole for musicians, misfits and drifters with great stories and bad credit.

Everyone’s been here. Buffett, Hunter S. Thompson (allegedly). That one guy who claims to have invented Jell-O shots (but he didn’t).

It’s the kind of place where you can lose time, lose your voice but also find God in the form of a guy with a harmonica and no shoes.

Final bite: Key West doesn’t just serve food, it serves folklore

Sure, you can eat in Key West. But that’s like saying you can swim in a volcano. These places aren’t just restaurants They are tales that you tell in case you want to ward off death by making it think twice about the kind of desperado it’s trying to pinch.

Some of the best meals of your life will be eaten while sweating through your flip-flops, staring at a wall covered in rusty license plates and possibly blood, while a local explains how his cousin once dated Hunter Biden and still has the laptop. Yes, if you want the shirt, just ask the bartender, he’ll happily take it off and show you his abs.

Do you have a favorite restaurant in Key West? If so, let us know in the comments!