Key West: Haunted Pub Crawl Walking Tour

Key West: Haunted Pub Crawl Walking Tour offers a unique way to experience the island’s darker side, blending spooky stories with a casual pub crawl. This tour promises more than just drinks; it’s a journey through Key West’s mysterious past, told with engaging storytelling by a local guide. For those interested in history with a twist of the supernatural, it’s a perfect blend of entertainment and authentic local lore.

What We Love About This Experience:

• The knowledgeable guides, like Chris, who bring stories to life with passion and insight
• The mix of historical facts and spooky tales, making each stop more intriguing
• The small group size (limited to 9 participants), ensuring a personalized experience
• The variety of haunted pubs and historic venues, each with its own eerie backstory

One potential consideration is that drinks are not included in the ticket price, so you’ll need to budget for your own beverages. This tour best suits those who enjoy storytelling, history, and a good ghost story, especially if you like exploring with a drink in hand.

This experience made our article of The 16 Top Walking Tours In Key West: Which Is Best?.

What Is the Key West Haunted Pub Crawl Walking Tour?

This two-hour walking tour is a lively exploration of Key West’s haunted sites, combined with visits to some of the island’s most historic and spirited pubs. Led by a local guide, you’ll step into the shadows of the island’s past, hearing tales of ghostly apparitions, tragic events, and bizarre legends—all while making your way from bar to bar.

The tour is designed to give you a different perspective on Key West, emphasizing its darker stories that don’t always make it into travel guides. Instead of just sightseeing, you’ll experience the city’s spooky side firsthand, with stories that will give you goosebumps.

You can check availability for your dates here:

The Itinerary Breakdown

Starting Point: Captain Tony’s Saloon

The tour kicks off at Captain Tony’s Saloon, a lively spot with an eccentric reputation. This bar is famous for its bizarre decor—including bras on the ceiling and fake bodies beneath the floors—making it a fitting first stop. The guide will share stories about the peculiar tree in the middle of the bar, stained by its victims, and ghostly tales of spirits still lingering around the stools and bottles. As one reviewer noted, the stories here are “great and atmospheric,” setting the tone for the night.

Wine-O Bar & Lounge at La Concha Hotel

Next, you’ll head to the Wine-O Bar & Lounge, which resides inside one of Key West’s largest hotels, the historic La Concha. The building’s height has a dark history—being the site of tragic suicides—leading to reports of hauntings. The guide will recount the tragic backstory, giving you a glimpse into the emotional weight this location carries. Expect to hear about how tragic events can leave a lasting impression, especially in places with such history.

The Roost and Nearby Haunted Landmarks

From there, the group makes its way to The Roost, a popular bar known for its excellent cocktails. This stop is not just about drinks; it’s also about the stories that surround the Key West Theater and the Artist House nearby. The theater, once filled with children’s screams, is said to host lingering spirits, while the cursed doll at the Artist House adds a strange, unsettling flavor to the tour. The guide discusses how previous owners’ tragic stories have contributed to the ghostly activity.

More Great Tours Nearby

Dean-Lopez Funeral Home and the Necromantic Tales

Moving on, the tour explores the Dean-Lopez Funeral Home, once a place of intense obsession and tragic love stories. According to guides, a lover’s obsession turned deadly, with efforts to bring the dead back to life. These stories deepen the sense of eeriness and show how personal tragedies can echo through generations.

Old Town Tavern & Beer Garden

The final stop is Old Town Tavern & Beer Garden, an old-fashioned pub with a legendary past. The guide hints that Ernest Hemingway’s spirit might still be hanging around, given his famous connection to Key West. The stories here are a perfect mix of historical charm and ghostly whispers, rounding out the tour with a convivial yet spooky atmosphere.

What’s Included and What’s Not

The tour includes a professional tour guide and the experience of walking through Key West’s haunted sites. You’ll get a vivid narration of the island’s spooky past as you stroll from spot to spot. However, drinks and food are not included, so plan to purchase your own beverages at each pub. This gives you the flexibility to choose your preferred drinks, whether it’s a cocktail, beer, or something else.

Practical Details

The meeting point is conveniently located across from Shots and Giggles at the Key West Chamber of Commerce, ensuring easy access. The tour runs for approximately 2 hours, with starting times varying based on availability. It’s advisable to wear comfortable shoes and bring essentials like water, cash (for tips or extra drinks), and weather-appropriate clothing.

The group size is kept small (up to 9 people), which means more personal interaction and a better chance to ask questions. The tour is wheelchair accessible, making it inclusive for most travelers.

Why This Tour Is a Great Value

At just $30 per person, this experience offers a lot for the price. You’re paying for a guided walk through some of Key West’s most haunted locations, combined with fascinating stories and a chance to see the city differently. The fact that the tour is led by passionate guides, like Chris, who are praised for their storytelling skills, adds to the overall value.

Authenticity and Atmosphere

The descriptions of each site and the stories shared suggest that this tour balances entertainment with authenticity. Reviewers highlight the great stories and pub stops, and mention guides who connect well with the group, making the experience memorable. The inclusion of tales about haunted pubs, cursed dolls, and tragic events makes the tour stand out from typical bar-hopping nights.

The Social Experience

Joining a small group means you’ll get more personalized stories and interactions. The tour’s relaxed pace encourages mingling, making it ideal for solo travelers, couples, or small groups looking for a fun, spooky night out. Since the tour ends back at the starting point, it’s easy to continue your evening in Key West afterward.

Final Thoughts: Who Will Love This Tour?

This experience is best suited for travelers who enjoy stories with a spooky twist and are curious about the darker side of Key West. It’s perfect for those who like a mix of history, ghost tales, and socializing over drinks. If you prefer guided tours with local insight and a playful atmosphere, you’ll find this tour both entertaining and educational.

However, if you’re not comfortable walking or if you expect included drinks, you might want to plan accordingly. The tour’s price point and small-group setup make it an excellent choice for those seeking an authentic, engaging way to explore the island’s haunted corners.

Key Points

• Engaging guides like Chris make stories come alive with passion and local knowledge
• Historic pubs and haunted sites provide a fascinating backdrop for spooky tales
• The small group size ensures a personalized, intimate experience
• Two hours of walking and storytelling offers a relaxed, enjoyable pace
• Not included drinks allow for personal choice and budget flexibility
• Accessible and convenient meeting point makes participation straightforward

Frequently Asked Questions

Is this tour suitable for children?
No, the tour is designed for adults over 21 due to bar entry laws and the nature of the stories.

How long does the tour last?
It runs for approximately 2 hours, including walking and storytelling.

Are drinks included in the price?
No, drinks are not included. You’ll have the opportunity to purchase your own beverages at each pub stop.

Is the tour wheelchair accessible?
Yes, the tour is wheelchair accessible, making it suitable for most guests with mobility needs.

What should I wear?
Comfortable shoes are recommended since you’ll be walking for about two hours, and dress weather-appropriate.

Where does the tour start and end?
The tour begins across from Shots and Giggles at the Key West Chamber of Commerce and ends back at the same meeting point.

Can I cancel if my plans change?
Yes, you can cancel up to 24 hours in advance for a full refund.

In essence, the Key West Haunted Pub Crawl offers a fun, slightly spooky way to experience the city’s hidden stories. It combines local history, ghostly legends, and lively pub stops into an evening that’s both entertaining and memorable. Whether you’re a history buff, ghost story enthusiast, or just looking for a distinctive night out, this tour provides good value and authentic charm.

You can check availability for your dates here: