The Most Haunted Bars in Key West

Posted: 05.15.2025 | Updated: 05.15.2025

Travelers from all over, even Sunshine State locals, head to Key West for its relaxed atmosphere, historical charm, and proximity to crystal-clear cobalt waters. Then there are those attracted to the spectral energy that flows through the Keys. 

With a history that predates even that of mainland Florida, Key West has witnessed deadly natural disasters, public executions, and slavery, somehow emerging on the other side as a beachy vacation destination. Catering to incoming travelers are establishments that flow with libations and tales of the otherworldly. 

The island is riddled with haunted locations, but few are as inviting as some of the best bars in Key West. While others flock to meet Robert the Doll, you can kick back with a cold one and get acquainted with other Key West ghosts. From the mysterious urinal provided by Hemingway to one of the writer’s former haunts, several bars in Key West offer a spooky good time.

Order your favorite drink and prepare to meet one of the island’s ethereal residents on a Key West ghost tour with Southermost Ghosts. Bars tend to bring a different energy than most haunted locations, their aura manipulated by the social atmosphere. This makes them perfect for a more lighthearted stop, though not one free of moving glasses and shadowy strangers. 

What is the most haunted bar in Key West?

If it’s spirits and spirits you’re looking for, anyone in the know will point you to Captain Tony’s Saloon. Often described as Key West’s most haunted bar, this joint on Greene Street was originally known as Sloppy Joe’s, which might be confusing since there’s a different Sloppy Joe’s on Duval Street. With a morbid history that includes the island’s first morgue and a brutal familicide, it’s no wonder Tony’s earned accolades for being the city’s most haunted bar.

General Horseplay

Tucked within a red brick facade, just beyond the white balustrade, is a space rich in atmosphere. Its red coloring feels like a reference to its resident specter: Wilford “Red” Williams. Red has been stopping by General Horseplay for years. Longer than anyone else, in fact. He’s such a staple that the bar gave him a signature drink.

Unfortunately, Red will never get to taste the concoction of gin, bitters, raspberries, lime, and soda. He passed away in the 90s, leaving behind the legacy of the bar he co-owned, Red’s Place. Eventually, after its second owner, Ryan, died, the space became General Horseplay. Despite the name change, Williams remains anchored to the building.

When he’s not watching the bar, Red is back by the bathrooms, gloating about his prized possession. Legend has it that Ernest Hemingway, a friend of Red’s, used to frequent another nearby hotspot: Sloppy Joe’s (later Captain Tony’s). 

During one particular drunken evening, Hemingway exclaimed he would be taking one of the bar’s urinals. After all, he’d spent so much money there. The whereabouts of said urinal is up for debate, but Red’s spirit claims it’s in the back bathrooms of General Horseplay. He’s a harmless haunt, but maybe lingering by the bathrooms isn’t the best spot for his spectral energy. 

Captain Tony’s Saloon

As previously mentioned, Captain Tony’s Saloon was once known as Sloppy Joe’s. It was Ernest Hemingway’s favorite hangout. 

Behind the scenes, both Captain Tony’s and the current Sloppy Joe’s on Duval Street have been locked in a legal battle to determine who owns the trademark. Though there’s a third contender to muddy the waters, one thing remains true: it’s Captain Tony’s that has the history to support that it is heavily haunted.

Before its conversion into Captain Tony’s, the building had a rather dark purpose in Key West. In 1851, the building that would later welcome Hemingway was purpose-built as a morgue. It was Key West’s first, which would be useful over time, especially when it also became the island’s “Hanging Tree.” 

Here, 16 pirates were hanged for their crimes. As was one of Captain Tony’s spectral visitors: the Lady in Blue. The unnamed phantom was brought to the Hanging Tree after stabbing her husband and two children to death. Her ghostly name comes from the blue dress she donned on the day of the murder. Some believe it’s also a reference to the color her skin turned after the noose tightened.

Before Sloppy Joe’s opened in 1933, the building was converted into a bordello, outfitted as a cigar factory, then turned into a speakeasy. What debauchery unfolded within the prohibition era escape has been unrecorded, but chances are it lent to the spectral energy that courses through Captain Tony’s. 

Along with the Lady in Blue, Captain Tony’s is said to be haunted by Elvira Drew, alleged to have killed her husband in self-defense. Even more curious is the gravestone that sits beneath the still-standing Hanging Tree. This belonged to Reba Sawyer, whose husband moved the stone to the bar after discovering her affair. 

Shots and Giggles

It was an unfortunate tragedy that led to Shots and Giggles’ haunted history. Today, a bar inviting locals and travelers to enjoy a menu full of libations, Shots and Giggles was once home to Frank Fontis. 

An eccentric man with a few demons of his own, Fontis tried to leave behind a legacy to be proud of. When he opened the Coffee Mill and Florida Railroad Museum, the opportunity was within his grasp.

Sadly, Frank let his gruff and odd personality get in the way. Before long,  his museum had a rather stringent set of rules that could get anyone banned. What started with a sensible “no littering” policy escalated until he began scrutinizing nearly everyone who walked through the door. When he refused to pay his workers, who tended to be AWOL sailors and vagrants, Frank all but sealed his fate. 

On January 5, 1979, his nude body was found on his front porch. Blood pooled around him, drained from the bullet wound in his head. Shortly after, his treasured museum closed, and his home was eventually converted into Shots and Giggles. It’s said that wildlife can sense his spirit. When he’s in a particular mood, nothing comes near the drinking hole. 

Bull and Whistle

The artistic renderings adorning the walls of this multi-faceted bar depict Key West’s unique and eclectic history. A bull head juts out of one wall, playing on the name of the first-floor venue, The Bull. The space carries an old-school charm, pulling guests back in time with its rustic decor and atmosphere. Upstairs, a more modern retreat awaits in the form of The Whistle Bar. It’s also here where visitors are likely to encounter one of Bull and Whistle’s resident haunts. 

According to local lore, during a remodel, workers built an inactive telephone into a wall. Despite having no way of working, some have claimed to have heard it ring. The phantom caller tries and tries again, to no avail. 

However, it may also be the ethereal trickster believed to have been cremated and hidden within the walls. Several past employees had this done, and at least one returned with a love for practical jokes.

Back on the first floor, an old-timey pharmacist silently waits for a drink. He never says a word, but when a drink is poured for him, he tends to vanish. There are no known stories of a pharmacist having been killed in the bar, so it’s more likely someone returning to what was their favorite spot before their death.

First Flight Island Brewery

The First Flight Island Brewery has quite an intriguing history. One that ties directly into its name and the ethereal entities anchored to the bar. In its heyday, the brewery was a ticket office for Pan American Airlines, and it was here that the very first tickets were sold. 

Though Pan Am eventually shuttered, echoes of its past remain part of the brewery. 

Ed Musick was among Pan Am’s esteemed pilots and had been a pioneer of the transoceanic route across the Pacific. Aboard the China Clipper, he made it as far as the Philippines.

Unfortunately, he took his final flight on January 11, 1938. He and his crew of six were killed in a mid-flight explosion caused by an emergency fuel dump. Ed left behind his wife, Cleo, who, for First Flight, is the real star of this story. 

Cleo died in 1974, and ever since has been a fixture of the brewery. Many believe she’s still awaiting the return of her beloved. She may even have just returned to somewhere that reminds her of her dear Ed. 

Whatever the reason, she’s refused to leave First Flight, much like the other specters in the establishment. From a mysterious man in a zoot suit to a poltergeist in the upstairs bathrooms, the former Pan Am office sees its share of spectral activity.

Drink with Spirits in Key West

Raise a glass to the undead and the dearly departed. Bars are a comforting place for both the living and the dead, and the most haunted bars in Key West are welcoming watering holes where the two can coincide. 

Care to know more about the many spirits that roam the Floridian island paradise? Book your Key West ghost tour with Southernmost Ghosts and prepare for a journey into the unknown. You can better prepare by reading through our blog and keeping up with our spectral antics on Facebook, TikTok, and Instagram.

Sources:

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