Key West has plenty of beaches and bars, but some of the best things to do here are the odd ones: a cemetery with one-liners on its tombs, a museum full of six-toed cats, and a doll that people write apology letters to.
Here's a full day of them, hour by hour, from early morning to midnight.
For more along the same lines, see our lists of funky spots and hidden gems, and check what's happening today.
5:00 AM, those freakin’ roosters
Key West's chickens arrived with its people: settlers and the thousands of Cubans who came in the 1800s kept them for eggs and meat, and some of the roosters were fighting birds, set loose, local histories say, once cockfighting was outlawed.
They still live all over town, on walls, in bars and in the street, and the city has relocated more than 15,000 of them since 2009, Keys Weekly reported.
But before you go nuts, know this. Feeding them is against city law.
7:30 AM, the Key West Cemetery
One of my favorite spots on the island.
The Key West Cemetery sits in the middle of Old Town, nineteen acres of above-ground tombs, and early morning is a good time to visit, while it's cool and quiet.
WLRN went looking for the one-liners on its stones and found this on the cremation wall: "If you're reading this, you desperately need a hobby."
For the stories behind the graves, the Murder, Money & Margaritas Cemetery Walking Tour plays in your ear as you walk.
9:00 AM, build-your-own Bloody Mary
At Rams Head Southernmost there's a build-your-own Bloody Mary, with a spread of mixes and garnishes to choose from.
The bar says nobody else on the island does this, and the local word on our listing is that it's the best Bloody Mary in town.
You be the judge!
10:00 AM, Hemingway's six-toed cats
The Hemingway Home and Museum has nearly 60 cats (probably more, actually), all carrying the six-toed gene and about half of them showing it, the museum says.
The story goes that a ship's captain gave Hemingway a white six-toed cat named Snow White, and that some of today's cats descend from her.
Hemingway named his cats after famous people, and the museum still does. The last count it gave Garden & Gun was fifty-nine.
Noon, Visit Robert the Doll
Fort East Martello, an old brick fort run as a museum by the Key West Art & Historical Society, is home to Robert, a doll made by Steiff around the turn of the last century, according to his own website, who, the story goes, arrived in Key West in 1904.
He belonged to a boy named Eugene Otto, who blamed Robert for the trouble in the house, and the story has followed the doll ever since.
Robert has been at the fort since 1994, Keys Weekly reported, and people send him letters apologizing for taking his picture without asking, and blaming him for what went wrong afterward.
Pro tip: Ask before you take his picture. And oh yeah…admission to the fort isn't free. But it’s worth it!
2:00 PM, the Shipwreck Treasure Museum
Before tourism, Key West's wreckers made their living salvaging ships that ran aground on the reef.
In fact, all the money used to build Old Key West came from wrecking.
It made Key West the richest city per capita in the US back in the late 1800’s.
The Key West Shipwreck Treasure Museum tells that story with storytellers in period costume, pieces from the 1856 wreck of the Isaac Allerton and a 65-foot lookout tower.
4:00 PM, butterflies, flamingos and parrots
The Key West Butterfly & Nature Conservatory keeps some 1,000 butterflies of 50 to 60 species, the Florida Keys tourism council says, plus two flamingos, Rhett and Scarlett, a breeding pair.
The flamingos meet visitors in a daily session called Flamingle, six guests at a time, look but don't touch. Ask the conservatory for times.
Nancy Forrester's Secret Garden, which the tourism council describes as a parrot sanctuary and art environment started by the artist Nancy Forrester, rescues parrots, especially macaws.
6:00 PM, a bar in an old bank vault
Tiki House on Duval has a secret back bar that used to be a bank vault.
A block away, The Grand is in a Victorian mansion, with an almost secret bar in the back that's a quiet break from Duval.
7:00 PM, magic by the pool table
At Schooner Wharf Bar, a waterfront bar, Frank Everhart performs Frank's Comedy Island Magic Show back by the pool table on the nights he's on.
Our listing calls it the island's longest-running comedy bar magic show, and it's free.
But heads up! Frank takes a much-needed break on Mondays and Tuesdays.
8:00 PM, a true crime tour
The iWitness True Crime Tour walks Old Town for 90 minutes in the evening, telling real-life crime stories in the heart of Old Town, and the local word on our listing is that it has a surprise ending.
If you'd rather go on your own, the Legends of Key West Audio Tour uses your phone's GPS to play the right story at the right corner.
Midnight, the Conch Republic
On April 18, 1982, the U.S. Border Patrol set up a roadblock on the highway at the top of the Keys and stopped every car heading north. Traffic backed up and visitors stayed away.
Five days later, on April 23, Mayor Dennis Wardlow declared that Key West had seceded and become the Conch Republic. He told NBC Miami years later that if they were going to be treated like a foreign country, they would become one.
The Republic's own history says the "war" that followed involved stale Cuban bread, that it surrendered almost at once, and that it then asked for foreign aid.
Every April the island celebrates its independence with a festival that runs about ten days.
But if you’re not here in April, go check out The Bull and the murals on the wall. If Key West had a Louvre, The Bull would be it.
For more ideas, see what's happening today, the last-minute deals, and our lists of funky spots and hidden gems.
Sources
- Key West Art & Historical Society: Fort East Martello
- Keys Weekly: Key West's haunted doll (2020)
- Robert the Doll
- Hemingway Home and Museum: Our cats
- Hemingway Home and Museum
- Garden & Gun: Hemingway's six-toed cats
- The Conch Republic: Our founding in 1982
- Keys Weekly: the Conch Republic roadblock (April 18, 1982)
- NBC Miami: Florida Keys celebrate 40th anniversary of the Conch Republic (2022)
- WLRN: Key West Cemetery, where last words are sometimes one-liners (2016)
- City of Key West: Historic City Cemetery
- Florida Keys & Key West: Flamingle encounter
- Florida Keys & Key West: Nancy Forrester's Secret Garden
- Key West Shipwreck Treasure Museum
- Key West The Newspaper: Key West's chickens
- Florida Rambler: Key West chickens and roosters
- Keys Weekly: Don't feed the chickens (2025)
