Key West: Haunted Pub Crawl Walking Tour

Imagine wandering through the lively streets of Key West, but with a fascinating twist — learning about its darker, haunted past while enjoying a drink or two. The Haunted Pub Crawl Walking Tour promises a lively, atmospheric evening filled with eerie stories, haunted pubs, and a glimpse into the island’s ghostly legends. It’s run by Ghost City Tours, known for combining storytelling with authentic local history, and it’s a solid choice for anyone looking to add a spooky layer to their Key West experience.

One aspect we really appreciate is how this tour mixes entertainment with genuine local tales. The guides seem passionate and knowledgeable, sharing stories that keep you on the edge of your seat, all while exploring some of the most atmospheric pubs in town. That said, one thing to keep in mind is that the tour is primarily focused on storytelling and walking, so it’s more about the ambiance and stories than a pub crawl in the traditional sense. It’s ideal for travelers who enjoy a good story, a bit of history, and don’t mind walking between stops. Perfect for those interested in the haunted lore of Key West paired with a fun, social evening.

Key Points

• Authentic stories: The tour features detailed tales about haunted locations, including infamous cases and local legends.
• Guided by experts: Guides like Chris bring stories to life with enthusiasm and local insight.
• Atmospheric stops: Visits to some of Key West’s most haunted pubs and historic sites.
• Walking experience: A 2-hour stroll through the charming, eerie streets with minimal downtime.
• No drinks included: You’ll need to bring cash or your own drinks for the stops.
• Small group: Limited to 9 participants, creating an intimate, engaging atmosphere.

An In-Depth Look at the Haunted Pub Crawl Experience

The Setting and Atmosphere

Starting just across from Shots and Giggles on Ann Street, the tour kicks off in the open area of the Key West Chamber of Commerce. From the outset, it’s clear that this isn’t your average pub crawl — it’s an exploration of the island’s ghostly tales and spooky sites. With a small group of up to nine people, you get a more personalized, conversational experience, with plenty of opportunities to ask questions and engage with your guide.

The tour lasts about two hours, which is just enough time to get immersed in the stories without feeling rushed. Walking at a leisurely pace, you’ll explore Key West’s streets, learning about its lesser-known yet still famous haunted spots. The evening atmosphere, combined with the historical background, makes it both fun and slightly chilling.

First Stop: Captain Tony’s Saloon

Your journey begins at Captain Tony’s Saloon, a spot famous for its eccentric decor — bras hanging from the ceiling, strange fake bodies beneath the floorboards, and a peculiar tree at its center. The guide will share tales of the bar’s peculiar spirits and ghostly legends, including stories of victims whose spirits are said to still roam the stools and bottles. As one reviewer noted, “Chris was an excellent guide. Her connection to the Keys was felt.” It’s clear that guides like Chris bring an extra layer of authenticity and passion to the experience.

Second Stop: Wine-O Bar & Lounge

Next, you’ll head over to the Wine-O Bar & Lounge, located within the historic La Concha Hotel — the largest building in Key West. This spot has a tragic reputation for its history of suicides, which has led to reports of hauntings. The stories make you reflect on the darker side of the island’s history, contrasting with the lively atmosphere of the bar. It’s interesting to note that one reviewer mentioned the guide’s storytelling making the haunted stories very vivid, adding a touch of realism to the ghostly tales.

The Haunted Highlights: Theatres and Historic Homes

Your walk continues to The Roost, renowned for its cocktails, and nearby, the historic Key West Theater. Once a place of children’s screams, it’s now haunted by echoes of the past, and stories about cursed dolls at the Artist House add to the eerie vibe. The guide recounts chilling tales of the Dean-Lopez Funeral Home, where a lover’s obsession is said to have summoned supernatural forces in a tragic attempt to bring back the dead.

Final Stop: Old Town Tavern & Beer Garden

The evening winds down at the Old Town Tavern & Beer Garden, an old-fashioned pub that might be frequented by the spirit of Ernest Hemingway himself. The stories about Hemingway’s ghost and other spirits lingering in the area really bring the night to a memorable close.

What You Can Expect During the Tour

Stories with a Drink in Hand: The tour is designed for a relaxed, social experience — you’ll hear spooky stories at each location while sipping your own drinks, which you need to bring yourself as drinks and food aren’t included. Many reviews mention that guides like Chris are very engaging, sharing stories that keep even the most skeptical listeners intrigued.

Authentic, Local Insights: Guides do more than just read from a script — they share local lore, personal insights, and sometimes even lesser-known tales that aren’t found in tourist brochures. This personal touch makes the experience more memorable.

Visiting Haunted Pubs & Landmarks: The stops aren’t just bars — they’re historic spots with real stories behind them. The combination of storytelling and atmospheric locations creates a mood that’s both entertaining and slightly spine-tingling.

A Walk Through Key West’s Nightlife & History: The tour blends the island’s lively nightlife with its ghostly legends, making it a unique way to see the town from an alternative perspective. It’s an evening that’s both fun and thought-provoking.

Is It Worth the Price?

At $30 per person, this tour offers a solid value. It’s a small-group experience, led by passionate guides, and includes visits to some of the most haunted spots in Key West. Since drinks are not included, you might want to budget extra for beverages, but the stories and atmosphere more than compensate. The fact that you’re walking through historic locations adds an authentic feel that many larger, bus-based tours might lack.

The Reviews Say It All

One reviewer praised Chris for her storytelling and the connection she felt to the Keys, emphasizing how engaging and genuine the guide was. Another mentioned the tour as being “very informative and fun,” highlighting the balance of entertainment and education. The stories of haunted history, combined with great pub stops, make for a memorable night out that appeals to those interested in ghost stories, local history, or simply a different way to explore Key West’s nightlife.

Who Should Consider This Tour?

This tour suits those who enjoy storytelling, history, and a touch of the supernatural. It’s perfect for travelers seeking an authentic experience that combines history and entertainment without the need for physical activity or extensive walking. Because it’s a small, intimate group, it’s also ideal for couples or small groups of friends.

It’s important to note that participants need to be 21 or over to enter the bars, and you’ll need to bring your ID with you. If you’re a lover of ghost stories, haunted locations, or want a different perspective on Key West’s nightlife, this tour hits the mark.

Final Thoughts: Is the Haunted Pub Crawl Worth It?

If you’re after a fun, atmospheric evening filled with spooky stories and a chance to explore some of Key West’s haunted sites, this tour offers great value. The knowledgeable guides, especially those with local connections like Chris, bring stories alive with passion and detail. The small group setting means more interaction and a personalized experience, making it ideal for anyone who enjoys a mix of history, ghost tales, and a social atmosphere.

While drinks are not included, the stops at iconic pubs and the engaging storytelling make each moment worthwhile. It’s a lively alternative to typical bar-hopping, blending history with entertainment in a way that keeps everyone entertained. It’s best suited for those who are curious about the island’s darker side, love a good story, or want a memorable way to experience Key West after dark.

Frequently Asked Questions

Can I bring my own drinks?
Yes, since drinks and food are not included, you’re encouraged to bring cash and your own beverages to enjoy at each stop.

How long does the tour last?
The tour typically lasts around 2 hours, making it a perfect short evening activity.

Where does the tour start and end?
The meeting point is across from Shots and Giggles at the Key West Chamber of Commerce (201 Ann Street). The tour ends back at the same location.

Is it suitable for non-drinkers?
While the tour is designed around pub stops, the focus is on storytelling. Non-drinkers can still enjoy the stories and explore the haunted sites, but note that alcohol consumption is part of the experience.

Do I need to book in advance?
Yes, booking is recommended. You can cancel up to 24 hours in advance for a full refund, offering flexibility in case of changes.

Are there any age restrictions?
Yes, participants must be 21 or older to enter the bars, so the tour isn’t suitable for minors.

Is the tour wheelchair accessible?
Yes, the tour is listed as wheelchair accessible, but it’s always good to confirm specific needs when booking.

What should I bring?
Bring your ID or passport, comfortable shoes, water, insect repellent, and weather-appropriate clothing. Cash is recommended for drinks or tips.

In the end, this Key West haunted pub crawl offers a unique blend of eerie stories and atmospheric locations, perfect for anyone looking to spice up their evening with a touch of ghostly intrigue. Whether you’re a history buff, a ghost story aficionado, or just looking for a fun, social way to see the town, this tour delivers charm, chills, and a good dose of local lore.