The Dark Side of Key West Ghost Tour

Key West is celebrated for its lively streets, colorful characters, and laid-back vibe, but beneath the fun-loving surface lies a more mysterious story. The Dark Side of Key West Ghost Tour is a 90-minute walk that takes you through some of the island’s most haunted spots, revealing stories of spirits, legends, and eerie happenings. For just $34.99 per person, you get a chance to see the city in a different light—one filled with ghostly whispers and historical intrigue.

What we love about this tour is its well-curated stops and engaging storytelling—each site is carefully chosen for its spooky tales and historical significance. The guides, often praised for their knowledge and charisma, make the stories come alive, turning a simple walk into a memorable experience. Another highlight is the balance of entertainment and authentic history, giving you enough chills without feeling like a scare fest.

A potential consideration is the timing—the tour starts at 9:00 pm, which makes it perfect for a night adventure but might not suit those who prefer daytime sightseeing. Also, the tour is limited to guests 16 and older, so it’s not ideal for families with young children.

This experience is ideal for history buffs, ghost story enthusiasts, and anyone curious about Key West’s darker tales, especially those who enjoy a good story told with enthusiasm and a dash of humor. If you’re looking for a fun, atmospheric way to explore the night streets of Key West, this tour offers a compelling blend of stories, history, and a touch of the supernatural.

Key Points

• Authentic Haunted Sites: The tour visits real landmarks like St. Paul’s Episcopal Church and Capt. Tony’s Saloon, each with ghost stories that make history feel alive.
• Engaging Guides: Tour guides, often praised for their knowledge and storytelling skills, significantly enhance the experience.
• Nighttime Atmosphere: The evening walk creates a spooky ambiance, perfect for the ghostly tales told along the route.
• Balanced Length and Price: At 1 hour 30 minutes and $34.99, it offers good value for a memorable night outing.
• Limited Access: Only outdoor sites are included; interior visits are not part of the tour, which keeps the pace brisk but limits access.
• Age Restriction: Designed for guests 16+, making it more suitable for teenagers and adults interested in ghost stories.

A Detailed Look at the Dark Side of Key West Ghost Tour

Setting the Scene: Meeting Point and First Impressions

The tour begins outside St. Paul’s Episcopal Church on the corner of Duval and Eaton Streets. This location is a fitting starting point—its Gothic architecture and whispers of ghostly lantern lights in the belfry set an atmospheric tone. The churchyard is said to be haunted by hundreds of disturbed graves, with visitors reporting cold touches and spectral figures in stained glass. Standing here, you immediately sense the layers of history and mystery that make Key West’s darker stories so compelling.

The Artistic House Bed and Breakfast: Eerie Victorian Charm

Next, you move to the Artist House Bed and Breakfast, once home to eccentric painter Robert Eugene Otto. The house’s ornate Victorian facade and blood-red gables make it both striking and slightly unsettling. Guests have reported strange footsteps, whispers, and feeling watched—classic signs of a haunted property. The legend of Robert the Doll, once housed here, adds a layer of cursed lore, making it a favorite among ghost enthusiasts. The stories shared at this stop are vivid, and many mention the sense of a lingering presence that enhances the spooky vibe.

Dean-Lopez Funeral Home: Resting in Cool Silence

Tucked away in a quiet neighborhood, the Dean-Lopez Funeral Home is more than just a place to say goodbye—it’s a site packed with ghostly tales, including the legend of Count Von Cassel, a European aristocrat whose spirit is thought to remain. This stop highlights the idea that some deaths and unfinished deeds tether spirits to the mortal world, making this a particularly intriguing stop for those fascinated by unseen attachments.

La Concha Hotel: Tall, Haunted, and Tragic

The La Concha Hotel is a prominent fixture on Duval Street, once the tallest building in Key West. Known for tragic stories of guests who leapt to their deaths from its rooftop bar, the hotel’s ghostly reputation persists despite renovations. Staff stories about restless spirits and unexplained phenomena add to the allure. Standing here, you get a sense of the hotel’s historic grandeur and the darker tales that echo through its halls.

Marrero’s Guest Mansion: Love, Loss, and Apparitions

Behind wrought-iron gates, Marrero’s Guest Mansion offers a romantic yet haunting story. Guests often report the scent of rose perfume and the feeling of unseen hands brushing their hair. The mansion’s love story turned ghost tale is a classic reminder that some spirits linger because of their unresolved feelings or relationships. It’s a gentle but effective way to show how emotional ties can translate into ghostly encounters.

322 Duval Street: The Oldest House’s Haunted Walls

The Oldest House in Key West is more than just a historic building; it’s a place where generations of shipwreck survivors, soldiers, and other spirits are said to still make their presence known. Its weathered walls have witnessed centuries of history—and possibly, hauntings. Visitors report the house “watches back,” making it a captivating stop that underscores how history and spirits can intertwine.

Audubon House & Tropical Gardens: Daylight Beauty, Nighttime Secrets

Built by Captain John Geiger, the Audubon House is renowned for its lush gardens and birdlife. Yet at night, the house whispers stories of former residents and the spirits that still walk its halls. Guests have noted that while the daytime is peaceful, the night brings an eerie sense, adding a surprising twist to what seems like a tranquil setting. This stop beautifully combines natural beauty with ghostly legend.

Capt. Tony’s Saloon: From Morgue to Haunted Pub

Finally, the tour ends at Capt. Tony’s Saloon, a historic bar built on the site of the original city morgue and hanging tree. Its walls are soaked in stories of death, despair, and spirits that never left. Many mention the ghostly presence, and some even suggest that the spirits “share” the space with the patrons. This lively yet haunted pub encapsulates the transition from the dark past to lively present, making it a fitting finish.

The Experience: What’s It Like to Walk With Ghost Stories?

Walking through Key West at night amplifies the spooky stories. The group size typically stays small—reviews mention groups of around 4 to 30—which makes for a more intimate and engaging experience. The guides, often praised for their entertaining and knowledgeable narration, bring the tales to life with humor and drama, balancing spooky with fun.

The timing at 9:00 pm feels just right—dark enough to set a mysterious mood but not so late that it feels rushed or overly eerie. The outdoor stops keep the pace brisk, though some might wish for interior visits; however, that would change the dynamic and perhaps extend the experience beyond its current scope. Expect to walk through historic streets, hearing stories of spirits, tragedies, and legends that have persisted for generations.

What Reviewers Say

Many guests praise the guides’ storytelling skills — with comments like “Jude was great and entertaining” and “Christian was awesome,” highlighting how the guides’ enthusiasm and knowledge make the tour memorable. Several mention the stories of Robert the Doll and the haunted buildings, emphasizing that the tales are well-told, with enough authenticity to send a shiver down your spine.

Some reviews mention a more personal touch—especially when the guide tailored stories for smaller groups or went out of their way to include extra stops. One reviewer said, “Our guide really tried to incorporate extra stories,” reflecting how the intimate setting enhances the experience. On the downside, a few guests found the tour “super disappointing” due to guide presentation issues, reminding us that the guide can make or break this experience.

Value and Practicalities

For $34.99, this tour offers a good value considering the length, storytelling quality, and unique access to some of Key West’s most haunted sites. It’s a walking tour, so comfortable shoes and weather-appropriate clothing are recommended. The 90-minute duration makes it a manageable evening activity, especially if you’re exploring the city in the evening.

The group size limit of 30 ensures you’re not lost in a crowd but also need to book in advance—most people are booking around 18 days ahead. Tips for the guide are customary but not included, so consider bringing some cash if you want to show appreciation.

Who Should Consider This Tour?

This ghost tour is ideal for adults and teenagers 16+ who enjoy stories of the supernatural, history, or local legends. It suits those who prefer outdoor exploration and storytelling over interior visits. Perfect for a night out with friends or a romantic walk, it’s also a great choice for anyone interested in Key West’s more mysterious side.

FAQ

Is this tour suitable for children under 16?
No, the tour is only for guests aged 16 and older.

Does the tour include interior visits of any buildings?
No, the stops are all outdoor landmarks; interior access is not part of the experience.

What is the tour duration?
It lasts approximately 1 hour and 30 minutes, making it an easy evening activity.

Where does the tour start and end?
It begins outside St. Paul’s Episcopal Church on Duval Street and ends at Capt. Tony’s Saloon on Greene Street.

Is the tour wheelchair accessible?
The tour is near public transportation and requires a moderate physical fitness level, so some mobility limitations might need consideration.

Are pets allowed?
Service animals are permitted; other pets are not mentioned as allowed.

What should I wear?
Comfortable walking shoes and weather-appropriate clothing are recommended, especially since it’s an outdoor evening walk.

Can I cancel or reschedule?
Yes, there’s free cancellation up to 24 hours before the tour. Less than 24 hours, and refunds are not available.

Final Thoughts

The Dark Side of Key West Ghost Tour offers a compelling way to combine history, storytelling, and a good dose of spooky intrigue. Carefully curated landmarks and guides with a flair for storytelling make it a standout experience for those curious about the island’s haunted reputation. The evening walk creates a perfect atmosphere for ghost stories, and the small group size ensures an intimate experience.

If you’re looking for a fun, atmospheric way to explore Key West’s darker past—without interior visits or long tours—this experience delivers. It’s best suited for those who enjoy genuine stories told with enthusiasm and appreciate a little thrill with their history. Whether you’re a skeptic or a believer, you’ll walk away with a new appreciation for the mysterious stories that haunt this charming island.

Complete Tour Data

Title: The Dark Side of Key West Ghost Tour
Rating: 4.5
ReviewCount: 334
Location: Key West, USA
Price: $34.99 per person
SupplierName: Ghost City Tours of Key West
SupplierPhone: +18559990491
SupplierEmail: [email protected]
ReviewBreakdown: 277;27;4;3;23
Review1: 4|cherylynne331|May 2025|A good guide who tried to go the extra mile|There were only four participants on our tour, so our guide really tried to incorporate a couple of extra stops and stories that would not have been possible with a larger group. the tour itself was pretty good, probably one of the better ghost tours I’ve been on.
Review2: 5|Kristopher_P|May 2025|Jude was great and entertaining|Jude was great and entertaining. The stops all had a great story to tell. Jude was very knowledgeable.
Review3: 5|Brink_S|Apr 2025|Christian was awesome! …|Christian was awesome! She entertained us and told the ghost stories with excitement and kept us engaged.
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