Walk into Captain Tony's Saloon and you're immediately struck by the atmosphere—not just the dive bar charm and the layers of business cards, bras, and dollar bills covering every surface, but something else. There's a heaviness in the air, a feeling of being watched, and the unmistakable presence of the enormous tree trunk that grows up through the middle of the bar and out through the roof.
This isn't just any tree. It's the hanging tree—Key West's execution site where pirates, criminals, and those who ran afoul of island justice met their end swinging from its branches. The bar was literally built around this tree, incorporating into its structure a piece of Key West's darkest history.
Bartenders work late shifts knowing they're not alone. Glasses move on their own, cold spots appear in the tropical heat, and the spirit of Elvira—a woman who died here decades ago—is regularly encountered by staff and guests. On our Key West Haunted Pub Crawl, guests frequently report seeing shadow figures, feeling sudden temperature drops, and experiencing the unmistakable sensation of unseen hands touching their shoulders or hair.
The History of Captain Tony's Saloon
The building that now houses Captain Tony's Saloon was constructed in 1851 and originally served as an icehouse and morgue before becoming a bar. The location was deliberately chosen despite—or perhaps because of—the massive tree that dominated the property. This tree had served as Key West's hanging tree since the early 1800s, a place of public execution where condemned criminals were hanged before gathered crowds.
The tree's dark history was well known, but frontier Key West was a practical place where land was scarce and the dead were quickly forgotten. When the building was constructed, rather than removing the tree, the builders simply incorporated it into the structure. The hanging tree became a central feature of the bar, its trunk rising up through the building and its branches spreading across the roof.
In 1933, the location became Sloppy Joe's Bar, owned by Joe Russell, a close friend of Ernest Hemingway. Hemingway was a regular patron, and the bar became legendary as his favorite watering hole. In 1937, when Russell moved his bar to its current location on Duval Street due to a rent increase, the original building changed hands and eventually became Captain Tony's Saloon, named after Captain Tony Tarracino, a colorful Key West character who bought the bar in 1958.
Captain Tony ran the bar for decades, cultivating its reputation as a no-holds-barred dive where anything could happen and usually did. The bar attracted a rough clientele—sailors, fishermen, drifters, and locals who appreciated the lack of pretense and the strong drinks. Over the years, the bar witnessed fights, affairs, deaths, and all the drama that comes with being a 24-hour drinking establishment in a town famous for excess.
The Hanging Tree's Dark Legacy
The tree that grows through Captain Tony's has witnessed hundreds of years of Key West history, and much of it was violent. Historical records indicate that at least 75 people were hanged from its branches, though the actual number may be much higher. Pirates captured in Key West waters were often executed here as a warning to others. Criminals convicted of murder, rape, and other capital crimes met their end swinging from the tree's sturdy limbs.
The executions were public events, drawing crowds of islanders who viewed hangings as both justice and entertainment. Bodies were left hanging as examples, sometimes for days in the tropical heat, before being cut down and buried in unmarked graves nearby. Some believe the mass grave beneath the bar contains the remains of executed criminals, adding another layer to the location's haunted reputation.
The tree itself seems to resist the building's attempts to contain it. Despite being encased in the structure, it continues to grow, slowly pushing against the walls and ceiling. Some see this as the tree's refusal to be constrained by the building that was imposed upon it, while others believe the spirits of those who died in its branches keep it alive as a monument to their suffering.
Elvira's Mysterious Death
Among the many spirits said to haunt Captain Tony's, none is more frequently encountered than Elvira. According to local legend and the accounts of multiple bar owners and employees over the decades, Elvira worked at the bar decades ago, though the exact time period and her role vary in the telling.
What remains consistent is that Elvira died in the building under mysterious and tragic circumstances. Some versions of the story say she was murdered by a jealous lover, others claim she took her own life after a devastating heartbreak, and still others suggest she died in an accident or perhaps from illness while living in an apartment above the bar.
Her death wasn't discovered immediately, and her body remained in the building for some time before being found. The trauma of dying alone and undiscovered may explain why her spirit seems unwilling or unable to leave. Employees report that Elvira makes her presence known in multiple ways—moving objects, creating cold spots, appearing as a shadowy female figure, and occasionally manifesting strongly enough to be mistaken for a living person before vanishing.
The Spirits of Captain Tony's Saloon
Captain Tony's Saloon is one of the most actively haunted locations on our Key West Haunted Pub Crawl, with multiple spirits and frequent paranormal activity.
The Ghost of Elvira
Elvira is the most commonly reported spirit at Captain Tony's, and her manifestations are well-documented by staff and visitors. Bartenders describe feeling a presence behind them when working alone, turning to find no one there but sensing that someone was just watching them. Glasses and bottles move on their own, rearranging themselves overnight when the bar is locked and empty.
Multiple employees have reported seeing a woman in dated clothing standing in the corner of the bar or near the hanging tree, watching the activity with a sad expression. When approached, she vanishes—not gradually, but instantly, as if she was never there. Some witnesses describe her as appearing solid and three-dimensional until the moment she disappears, making them question whether they saw a ghost or a living person until she vanishes before their eyes.
The most disturbing encounters with Elvira involve physical contact. Bartenders report feeling someone touch their hair or shoulder when no one is nearby. Patrons sitting at the bar sometimes feel a tap on their shoulder, turning to find no one behind them. Others describe the sensation of being watched so intensely that they become uncomfortable and leave, only to learn later about the bar's reputation for hauntings.
On our Key West Haunted Pub Crawl, we've documented numerous guest experiences with Elvira. One guest reported feeling a cold hand grip her wrist while she was taking a photo near the hanging tree. When she looked down, no one was touching her, but the sensation of icy fingers remained for several seconds. Another guest's camera malfunctioned specifically when trying to photograph the area where Elvira is most often seen, working perfectly before and after but refusing to function in that one spot.
The Spirits of the Hanged
The hanging tree itself seems to be a focal point for paranormal activity, suggesting that the spirits of those executed here may linger. Visitors standing near the tree report sudden, overwhelming feelings of sadness, despair, and fear—emotions that don't match their actual mood and seem to come from outside themselves.
Some describe hearing whispers or cries when standing near the tree, sounds that seem to come from within the trunk itself. EMF readers show unusual spikes near the tree, and photographs often capture unexplained orbs, mists, or shadow figures in the vicinity.
Guests on our Haunted Pub Crawl have reported seeing shadow figures moving around the base of the tree, disappearing when directly observed. Others describe feeling suddenly short of breath or experiencing a choking sensation when standing too close to the tree, as if empathically experiencing the final moments of those who died hanging from its branches.
Tour Guest Encounters
The paranormal activity at Captain Tony's is so consistent that our guides on the Key West Haunted Pub Crawl expect unusual experiences here, and guests rarely disappoint. We've documented dozens of encounters, but several stand out:
A couple from Michigan photographed what appeared to be a translucent woman standing near the bar's entrance. In the photo, the figure is partially transparent, and furniture is visible through her torso. When they reviewed their photos later that evening, they discovered the figure appeared in three consecutive shots, moving slightly in each one, before disappearing entirely in the fourth photo.
A group of friends from Texas reported that their drinks kept moving while they stood at the bar. They would set a glass down, turn away momentarily, and find it had been moved several inches to a different spot. This happened multiple times, even after they began watching their drinks carefully. No living person could have moved the glasses without being seen.
Perhaps most dramatically, a solo traveler from California reported seeing a full-bodied apparition of a woman in old-fashioned clothing standing near the hanging tree. He watched her for nearly thirty seconds, long enough to note details of her appearance including her dark hair, pale skin, and sad expression. When he approached to ask if she was okay, she vanished instantly, and he realized he had seen Elvira. The experience was so vivid and disturbing that he left the bar immediately, only later learning about the location's haunted reputation.
Other Paranormal Activity
Beyond Elvira and the hanging tree spirits, Captain Tony's experiences various other unexplained phenomena. The jukebox has been known to turn on by itself, playing songs that no one selected. Doors lock and unlock without anyone touching them. Footsteps are heard walking across the upstairs area when the space is known to be empty.
Some visitors report feeling suddenly nauseous or dizzy in certain areas of the bar, particularly near the hanging tree or in the back rooms. These sensations pass quickly once they move to a different area, suggesting they may be picking up on residual energy or the presence of spirits.
The bar's numerous cats—Captain Tony's is famous for its resident felines—sometimes behave strangely, staring at empty corners, hissing at nothing visible, or refusing to enter certain areas of the bar. Animals are often more sensitive to spiritual presences than humans, and the cats' behavior provides additional evidence of the supernatural activity.
Security cameras have captured unexplained anomalies including shadows moving across empty rooms, objects appearing to move on their own, and strange lights or mists that appear and disappear without explanation. While skeptics might dismiss individual incidents, the sheer volume and consistency of paranormal reports from this location make Captain Tony's one of Key West's most genuinely haunted sites.
Visit Captain Tony's Saloon
Captain Tony's Saloon is located at 428 Greene Street in Key West and operates as a bar open to the public. The hanging tree and many of the bar's historic features are visible to all visitors, though the most intense paranormal activity is often experienced during quieter times or late at night.
Our Key West Haunted Pub Crawl stops at Captain Tony's Saloon, where our guides share the complete history of Elvira, the hanging tree, and the numerous spirits that haunt this legendary location. We discuss the documented paranormal encounters from our tour guests and explain why this bar has earned its reputation as one of the most haunted drinking establishments in America.
Join our Key West Haunted Pub Crawl to experience Captain Tony's Saloon and learn why some spirits choose to spend their eternity in bars where they can still be part of the living world's celebrations and sorrows.
