Explore More: Haunted Key West

By: Terry Ward

The attractive pastel-colored bungalows blooming with bougainvillea and happy-go-lucky Conch Republic citizens will likely be your first impressions during a port call in America’s southernmost slice of paradise. But delve deeper in conversation with the decidedly superstitious Key West locals and you’ll surely be regaled with fascinating tales of haunted places that bring the island’s history into full color.

Key West

Key West, it turns out, is one of the most haunted places in the country. With the island’s 19th century forts, free-wheeling past as a major port and to-this-day history of luring all manner of international drifters, sailors, artists, writers and merchants, that hardly comes as a surprise. And even if you don’t believe in ghosts, you’re sure to get a thrill from the historical tales tied to many of the island’s most purportedly haunted places. Ghost tour companies have of course capitalized on Key West’s eerie history with evening trolley tours and walking tours through Old Town’s bricked streets. But you can easily explore the island’s haunted history on your own during a daytime port of call by following our lead to these supposedly spirit-ridden spots:

CAPTAIN TONY’S SALOON, 428 Greene St.

Elvira Captain Tony's

Less than ten minutes from the cruise port by foot, this famous Key West watering hole located just off Duval Street was the original Sloppy Joe’s. Captain Tony’s is considered the oldest bar in Florida and attracts many a tourist keen to down a beer here for that very reason. And indeed, this no-frills bar where undergarments now dangle from the ceiling is where Hemmingway spent many an evening boozing and bantering between 1933 and 1937. But the haunted tie-ins at Captain Tony’s stretch back well before that to the building’s initial construction in 1851 when it was built as an icehouse that allegedly doubled as the city morgue. Note the gnarled tree in the middle of the bar that grows through the floor and exits the building through the ceiling. Dubbed the “hanging tree,” it served as a gallows back in the day when some 75 murderers, pirates and other ne’er do wells were said to have been hanged here by Key West’s enterprising (and take no prisoners) citizen vigilantes. The result? No shortage of ghostly sightings from the Captain Tony’s crowds, the most famous of which is that of a woman referred to as the “Lady in Gray.” She was supposedly hung here in her bloodied nightgown after murdering her husband and children, and bar workers and patrons claim to have spotted her ghostly presence in the women’s bathroom and elsewhere. In the billiards bar adjacent to the main one, look for a tombstone emblazoned with the name “Elvira” – it’s said to the final resting place of the coroner’s daughter. As with many things in Key West, the factual details are fuzzy and everyone seems to have a new take on Captain Tony’s history. But if, like many visitors, you notice the billiards room always feels a few degrees chillier than the main bar, you’ll at least have a few fun reasons to wonder why.

FORT EAST MARTELLO, 3501 S. Roosevelt Blvd.

East Martello Fort

You’re best off catching a taxi for the ten-minute ride to this incredibly well preserved bricked Civil War fort on the southeast side of the island – about as far away as you can get from the cruise port but well worth the trek. The fort’s construction dates to 1862, when the US Army built it as an added defense for Union-controlled Key West against a possible sea assault by the Confederates. In addition to the Civil War relics displayed inside and exhibits on sponging, wrecking and other erstwhile Key West industries, there’s a very ghostly twist to the museum here. And it has to do with a certain 19th century doll on display that has been attributed with causing all kinds of domestic chaos in Key West. Robert the Doll sits within a case of glass inside one of the fort’s exhibit rooms, and the wall behind him is full of letters from wary admirers – many begging for the doll’s forgiveness for not asking permission when snapping his photo (said to lead to all kinds of bad luck). The supposedly possessed doll was given as a gift to Key West painter Robert Eugene Otto in the early 1900s by his allegedly mistreated Caribbean nanny. And after causing too much public chaos in his various homes around the island, Robert was eventually moved to the museum where he became a tourist attraction. Rumor has it the doll has been seen moving his toy lion from knee to knee and tapping his glass encasing. Many Key West locals are so fearful of Robert, in fact, that they don’t dare enter Fort East Martello. If something misfortunate befalls you after a visit, just echo a common Key West refrain: “Robert did it.” And be sure to send him an apology letter, of course.

KEY WEST CEMETERY, intersection of Angela St. and Margaret St.

Key West Cemetery

Any cemetery is an obvious place for hauntings. But the history of Key West’s final resting place, in the northeast corner of Old Town, makes it worth visiting even if you’re not looking to reach out to the other side.  More than 100,000 people are allegedly buried here (many in unmarked graves), and the presence of above ground tombs – some stacked three or four high – lends a certain New Orleans-feel to the place. Here, plots for Cuban cigar makers and Civil War veterans lay alongside graves of yellow fever victims (the island was ravaged by the disease in the 1800s) Florida’s first millionaire (William Curry), family pets and Bahamian sailors. And the jumble of headstones are engraved with all kinds of curious mantras and remembrances. Look for one emblazoned with the cheeky words “I told you I was sick” and another dedicated to the memory of a pet deer named Elfina. Ghosts, naturally, have been spotted here, too. Consider yourself warned that sitting on gravestones or expressing any ridiculing words to the departed souls will not be met with kindness. Rumor has it that the ghost of a Bahamian woman buried here will be quick to approach you with a reprimand. Multiple visitors claiming to have been verbally assaulted by the lady were just as shocked when she vanished into thin air before their eyes. It goes without saying that you should be on your best graveside behavior.

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