Key West Dark Side History Walking Tour

Dare to walk the haunted heart of Key West—where the veil between the living and the dead is razor-thin. Your journey begins sweetly enough at River Street Sweets… but don’t let your guard down. From the cursed corridors of The Artist House—once home to the infamous Robert the Doll—to the haunted grounds of St. Paul’s Episcopal Church, something watches from the shadows. At Dean-Lopez Funeral Home, the air grows heavier with every step, while La Concha Hotel and Marrero’s Guest Mansion echo with screams that never made it into the history books. You'll pass on to the ghost-infested Oldest House, and the lush but sinister Audubon House, where spirits cling to the past. Your final stop? Captain Tony’s Saloon—built on bones, soaked in legend, and still home to the dead. This is not just a tour... it’s a test of courage.

Meeting Point

401 Duval St

401 Duval St, Key West, FL 33040, USA

The Corner of Duval Street and Eaton Street, outside of St. Paul's Episcopal Church. We will be directly across from River Street Sweets, located at 400 Duval Street.

What's included:

• An incredible tour guide and 90 minutes of spooky fun!

Not included:

• Gratuity
• No entry inside private locations
• Only for guests ages 16+

What to expect:

Duration: 1 hour, 30 minutes

St. Paul's Episcopal Church

401 Duval St, Key West, 33040-6550, Florida

The tour meets on the corner of Duval Street and Eaton Street outside of the gates of St. Paul’s Episcopal Church located at 401 Duval St, Key West, FL 33040.
In the heart of Old Town Key West, where the sea mist mingles with whispers of the past, stands St. Paul’s Episcopal Church—a hauntingly beautiful structure veiled in mystery. Locals speak of flickering lantern lights that appear in the belfry at midnight, long after the last soul has left. Beneath its grounds lie hundreds of forgotten graves, disturbed by storms and time, their spirits said to roam the churchyard restlessly. Visitors have reported cold touches on warm nights, spectral figures in the stained glass, and a phantom priest seen pacing the pews, murmuring prayers for the dead. Step lightly—at St. Paul’s, the line between heaven and haunting grows thin.

10 minutes

The Artist House Bed and Breakfast

534 Eaton St, Key West, FL 33040, USA

With its ornate Victorian facade and blood-red gables, the Artist House on Eaton Street is as enchanting as it is eerie. Once home to eccentric painter Robert Eugene Otto, it’s most infamous for sheltering Robert the Doll—a childhood toy said to be cursed, and perhaps possessed. Strange footsteps, whispered conversations, and the sensation of being watched are often reported by guests who dare to spend the night. Though Robert has since moved to a museum, some say his spirit still lingers, pacing the halls of his former home. The Artist House is not just a bed and breakfast—it's a portal into Key West’s most chilling legend.

10 minutes

Dean-Lopez Funeral Home

418 Simonton St, Key West, FL 33040, USA

Tucked among the quiet streets of Key West, the Dean-Lopez Funeral Home holds more than memories of the dearly departed—it holds the legend of Count Von Cassel. A mysterious European aristocrat with a taste for the macabre. Some say the Count’s soul never left, bound by obsession or unfinished deeds, still lingering in the cool silence of the embalming room.

10 minutes

La Concha Key West, Autograph Collection

430 Duval St, Key West, FL 33040, USA

La Concha Hotel rises like a grand sentinel over Duval Street, its historic walls soaked in luxury—and legend. Once the tallest building in Key West, La Concha became a tragic magnet for suicides—many leaping from its rooftop bar. But the most chilling tales come from hotel staff who say no amount of renovations can quiet the restless dead who checked in…but never checked out.

10 minutes

Marrero's Guest Mansion

410 Fleming St, Key West, FL 33040, USA

Behind the wrought-iron gates and lush palms of Marrero’s Guest Mansion lies a love story turned ghost tale. Guests report the scent of rose perfume in empty rooms, soft weeping in the night, and the sensation of unseen hands brushing their hair.

10 minutes

322 Duval St

322 Duval St, Key West, FL 33040, USA

The Oldest House in Key West holds more than history—it holds hauntings. Its weathered walls have seen shipwreck survivors, Civil War soldiers, and generations of restless souls. Step carefully—some say the house watches back.

10 minutes

Audubon House & Tropical Gardens

205 Whitehead St, , Key West, 33040-6522, Florida

Beneath the swaying palms and vibrant blooms of the Audubon House lies a darker tale than its beauty suggests. Built by Captain John Geiger, the home is said to be haunted by the very souls who once walked its grand halls. The birds may sing by day—but at night, the house whispers with the echoes of the past.

10 minutes

Capt. Tony's Saloon

428 Greene St, , Key West, 33040-6567, Florida

Captain Tony’s Saloon is more than a bar—but a crypt of Key West’s past. Built on the site of the original city morgue and hanging tree, the saloon’s walls are soaked in stories of death and despair. At Captain Tony’s, the spirits in your glass may not be the only ones you encounter.

10 minutes