The 5 Scariest Bathrooms in Key West

We have all seen some scary bathrooms in our lives, but beyond the splattered toilet rims and urine-soaked floors of Key West’s highest-trafficked establishments lie five locations with restrooms that are scary for an altogether different reason. Theories suggest ghosts appear near toilets because they are energized by the flow of water. Stories of spirits surprising humans who are taking care of business exist in several cultures, and though the Conch Republic is home to more than a dozen haunted bathrooms, we’ve narrowed the list to five of the best Bone Island bathrooms where there is a good chance something otherworldly might scare the shit out of you.

  1. General Horseplay | 423 Caroline Street

General Horseplay may host the most intriguing bathroom in the Florida Keys, as it has a rare double urinal. One person can use it just fine, but it is designed for two. If a second person joins in, the patrons find themselves standing face to face with just inches of porcelain separating them. The bathroom is built under a staircase, so an awkward head angle adds to the fun. An old-timer once told me this was the infamous urinal Ernest Hemingway took from Sloppy Joe’s, but the island is full of Hemingway tales.

 Visitors encounter the spirit of an older man near the bathroom entrance. He doesn’t talk to anyone, but if you speak to him, he’ll walk into the restroom and nod as if he wants you to follow. Few people do. More often, people wait for him to come out so they can take their turn, but the door never opens. They always discover the bathroom empty, despite what they saw.

Legend holds that the building was a make-shift morgue after a hurricane, but it was also a favorite hangout for Hemingway’s sometimes fishing captain and Red’s Bar namesake, Wilfred Williams. Many believe the older man is Red looking to show off the bars’ Hemingway connection.

2, Captain Tony’s | 428 Green Street

Captain Tony’s Saloon puts the legends in legendary. Captain Tony was a storyteller, and though the origin stories of many of the hauntings associated with the bar are sometimes hard to swallow, there is no denying the saloon is home to one of the most haunted bathrooms in Key West.

Stories abound about an unfortunate adulterer hanged from the tree that grows through the bar’s roof. She was wearing a blue nightgown when she perished, and as the life left her body, her face turned the same color as her gown. Today the Lady in Blue holds doors or turns locks in the ladies’ room. A boy once ran from the men’s room crying and told his mom a mean lady in there said she wanted to cut him. Guys beware if a lady in a blue nightgown approaches you at the urinal and asks, “How’s it hanging?”

 3. First Flight | 301 Whitehead Street

First Flight has a fantastic haunted history that includes ghosts of former employees from when the main structure was a ticket office for Pan Am, but it is toilet paper – not airplanes – flying around in the upstairs ladies' room. Rolls of Charmin fly over the stall when only one human is in the restroom. A former manager reported mystery stones that appeared in the sink. A single stone every day until the sink was overflowing with them.

The identity of this bathroom spirit remains a mystery.

 4. Key West Theater | 512 Eaton Street

The oldest Baptist Church in Key West had a bad relationship with fire. According to some legends, it burned in 1866 at the hands of a jealous minister. Several children are said to have died during the tragic event. It was torched again and burned to the foundation during the Great Fire of 1886, but it is an April 2, 1956 fire that lead to the resident spirit haunting the now Key West Theater’s relief station.

Billy Watkins Moody came to Key West in 1956 and was immediately drawn to the Baptist Church. He joined the congregation and after a few weeks was hired as an organist. On the night of April 2nd, Moody entered the church and headed to the choir room at the side of the altar. There he retrieved a candle but not to make an offering. Instead, Moody wrapped the candle in a brown paper bag, lit the flame, placed it on the altar, and returned home to sleep. The church burned to the ground.

 Bathrooms occupy the space where the old choir room was located. Faucets turn on by themselves, warm spots move across the floor, and the smell of burning wood fills the bathroom and quickly vanishes. People believe this is the ghost of Billy Watkins Moody. They say his spirit has returned to the church in hopes of being forgiven for his sins.  

5. Fort East Martello | 3501 S. Roosevelt Blvd.

Key West’s Civil War-era fort is famous worldwide as the home of Robert the Doll, but Robert is kept in good company by more than 42 documented spirits, including at least one that haunts the museum’s bathrooms.

Guests open the bathroom door only to have it yanked shut on them as if somebody is inside. They usually apologize and wait, but nobody ever comes out of the bathroom. When they try the door again, nobody is inside.

During the Civil War, the fort was a hospital, and many soldiers died of disease. The bathrooms are built in a part of the fort where bodies are thought to have been stored while awaiting burial.

Haunted Key West is the place to go for everything haunted in the Florida Keys. We are a collective of locals dedicated to the history and hauntings of the islands. Check back regularly for new blogs and updates to our free Haunted Directory.

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