Key West: Haunted Pub Crawl Walking Tour

Key West: Haunted Pub Crawl Walking Tour — A Spooky Night Out

If you’re after a different way to explore Key West, this Haunted Pub Crawl offers a mix of ghost stories, local history, and lively pubs all wrapped into a two-hour walking tour. For $35 per person, you’ll visit some of the island’s most intriguing haunted spots while enjoying a drink in hand. Led by a knowledgeable guide, this tour blends history, hauntings, and hospitality in a way that appeals to those curious about the darker side of paradise.

What we love about this experience is its informative storytelling combined with visits to famous pubs with a spooky twist. It’s a great way to get acquainted with Key West’s less-glamorous past, from demonic dolls to tragic stories. Plus, the small group setting makes it feel intimate rather than touristy. However, a potential consideration is that it’s an evening tour, so if you’re not a fan of walking around in the dark or standing in bars, it might not be for everyone.

This tour is perfect for history buffs, ghost enthusiasts, or anyone looking for a fun, atmospheric way to spend an evening. It’s especially suited for those interested in authentic stories told by guides passionate about the island’s mysterious side. If you enjoy a mix of history, a few drinks, and a little scare, you’ll find this tour quite rewarding.

You can check availability for your dates here:

Key Points

• Authentic stories: The guide shares lesser-known, spooky tales of Key West’s past.
• Unique pubs: Visit haunted pubs and restaurants with their own eerie histories.
• Evening walking tour: A two-hour stroll perfect for a relaxed, yet immersive experience.
• Informative guides: Guides like Chris receive praise for their knowledge and engaging storytelling.
• Atmospheric vibe: The combination of dark stories and lively bars creates a memorable mood.
• Accessible: Tour is wheelchair accessible and suitable for most adults over 21.

What to Expect on the Haunted Pub Crawl

This tour is designed to give you a taste of Key West’s haunted reputation while enjoying its local bars. It begins across from Shots and Giggles at the Key West Chamber of Commerce, a convenient starting point. From there, your guide—possibly someone like Chris, who receives rave reviews—will lead you through a carefully curated route of six or more historic and haunted locations.

Each stop holds its own story, from Captain Tony’s Saloon with its bras on the ceiling and fake bodies beneath the floors, to the Wine-O Bar & Lounge housed in a building associated with tragic suicides. You’ll hear about the demonic dolls and the necrophilia case that cast shadows over the city. These stories are told with just enough spookiness to send a few shivers, but never overly dramatized.

Captain Tony’s Saloon

This iconic bar is the first stop, famous for its eccentric atmosphere. Its floors hide fake bodies, and the tree in the middle is stained with the memories of victims. Expect a lively bar with a dark past, perfect for setting the tone.

Wine-O Bar & Lounge

Next, you’ll visit La Cocha Hotel’s Wine-O Bar, a site with its own tragic history. Its status as the tallest building in the area has made it a prime haunt for tragedies and suicides, adding a layer of authenticity to the ghost stories.

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The Roost & Key West Theater

The tour then moves to The Roost, renowned for excellent cocktails, and nearby Key West Theater, which apparently used to echo with children’s screams—a chilling detail that adds to its haunted reputation. The Artist House, once home to a cursed doll, is another stop that sparks curiosity.

Dean-Lopez Funeral Home & Old Town Tavern

You’ll learn about the lovers’ obsession gone wrong at the Dean-Lopez Funeral Home, and the stories of Ernest Hemingway’s ghost at the Old Town Tavern, located near his former residence.

The Experience of a Lifetime?

While the stories are the real highlight, the pubs themselves are worth the visit. They range from quirky and eccentric to historically significant, giving you a taste of local life along with ghostly tales. The mix of drinks and storytelling makes for a relaxed, yet intriguing evening.

The small group size, with reviews noting guides like Chris as informative and engaging, creates an environment where questions are welcomed, and stories feel personal. The 2-hour duration feels just right, allowing enough time to soak in tales without dragging on.

Practical Details

The tour costs $35 per person, which is quite reasonable considering the mixture of stories and bar stops. Be prepared to bring your ID (passport if you’re outside the US), wear comfortable shoes for walking, and carry cash for tips or additional drinks outside the tour. The tour is wheelchair accessible and usually available in the evening—a perfect way to cap off a day of exploring or relaxing.

Authenticity and Authentic Experiences

Many reviews praise the guides’ storytelling abilities and the genuine historical details shared, making this more than just a spooky pub crawl. The stories about Key West’s dark history are both entertaining and enlightening, offering a different perspective on this charming island.

One reviewer noted, “Chris was an excellent guide. Her connection to the Keys was felt,” highlighting how guides bring stories alive. Others appreciated the fun, entertaining atmosphere that blended humor with haunting tales, making the experience accessible and memorable.

The inclusion of local pubs is a real bonus—these aren’t tourist traps but established spots with their own stories, adding to the tour’s authenticity. The combination of history, spirits, and local flavor makes this a worthwhile outing for those who want more than just sightseeing.

Detailed Breakdown of the Itinerary

Starting point at Shots and Giggles is a strategic choice, as the location is central and lively. From there, your guide will take you on a roughly two-hour walk through the historic streets of Key West.

Each stop is carefully selected for its haunted reputation and its local significance. The Captain Tony’s Saloon is a must-see—the bar’s quirky decor and dark stories make it a favorite for fans of the macabre. Its reputation as one of the most haunted pubs in town earns it its place early in the tour.

The Wine-O Bar & Lounge offers a chance to hear about haunted buildings with tragic pasts, emphasizing how height and tragedy seem to be connected in this haunted landscape. The Key West Theater and Artist House provide narrative threads about the ghostly echoes of the past—stories of children’s screams and cursed dolls that keep the hauntings alive.

The Dean-Lopez Funeral Home’s creepy obsession stories and Hemingway’s ghost at the Old Town Tavern give the tour a personal and literary touch, tying ghost stories to the island’s famous residents.

What the Reviews Say

Feedback from those who’ve taken the tour consistently highlights the knowledge and enthusiasm of the guides. One person praised Chris, saying, “Super nice and very informative,” while another noted, “Great stories and pub stops!” The balance of storytelling and humor keeps the experience lively and enjoyable.

The small group setting was also mentioned as a positive, making it easier to engage and ask questions. Many felt the stories and history provided a unique perspective on Key West—they appreciated learning about its darker aspects beyond the typical beach and bar scene.

Final Thoughts: Is It Worth It?

If you’re interested in local history, ghost stories, or just looking for a fun, atmospheric night out, this tour offers great value. For $35, you get a combination of entertainment, education, and socializing in a relaxed environment. The two-hour duration makes it manageable even after a full day of sightseeing.

While the tour involves walking and standing, the pace is moderate, and the stories are engaging enough to keep your attention. It’s particularly suited for adults over 21 who want to experience Key West from a different angle—through its haunted tales and lively pubs.

Overall, it’s a well-reviewed, authentic experience that combines local lore with good drinks—a perfect way to spend an evening in this charming island city.

Frequently Asked Questions (FAQs)

Is there an age restriction for this tour?
Yes, the tour is only suitable for guests over 21 years old, as it involves visiting bars and alcohol consumption.

How long does the tour last?
The tour is approximately 2 hours, typically scheduled in the evening.

Where does the tour start?
It begins across the street from Shots and Giggles at the Key West Chamber of Commerce, located at 201 Ann Street.

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

What should I bring?
Bring your passport or ID, comfortable shoes, water, insect repellent, cash, and weather-appropriate clothing.

Are drinks included?
No, drinks are not included in the tour price, but you can purchase drinks at each pub as you go.

Can I cancel or reschedule?
Yes, you can cancel up to 24 hours in advance for a full refund. Keep in mind, reservations can be made now and paid later.

Are video recordings allowed?
No, recording videos during the tour is not permitted.

What makes this tour different from others?
It combines local haunted stories with visits to famous pubs, making it a unique blend of history and nightlife with guides praised for their storytelling skills.

In essence, this haunted pub crawl offers a lively, authentic look at Key West’s darker side, perfect for those who enjoy history, ghost stories, and a few drinks. We think it’s a fun, memorable way to experience a different facet of the island—one that’s best enjoyed with a curious mind and a sense of adventure.

You can check availability for your dates here: