Key West: Haunted Pub Crawl Walking Tour

Introduction

If you’re looking for a way to add a little spooky fun to your Key West trip, the Haunted Pub Crawl Walking Tour might be just the ticket. This experience promises to take you through some of the island’s most haunted spots, sharing chilling stories and eerie histories along the way. It’s a mix of ghostly tales, historic pubs, and a chance to see the city from a different perspective—all with a drink in hand.

What we really like about this tour are the engaging stories from local guides and the chance to explore Key West’s lesser-known haunted sites. Plus, it’s a relaxed, two-hour walk that doesn’t demand much more than comfortable shoes and curiosity. But, fair warning — if you’re not into ghost stories or drinking in historic bars, this might not be your ideal outing. It’s best suited for travelers who enjoy a mix of history, a bit of scare, and some good company.

You can check availability for your dates here:

Key Points

• Authentic stories and local guides make the experience engaging and genuine
• Visits to haunted pubs provide a fun, atmospheric setting for storytelling
• Two-hour walk makes it a manageable evening activity
• Age restriction: Not suitable for those under 21, so plan accordingly
• Price point offers good value for the combination of stories and bar visits
• Accessibility: The tour is wheelchair accessible

What to Expect from the Haunted Pub Crawl

This tour is designed to uncover some of Key West’s darker secrets, all while strolling through the historic streets. It’s a lively, atmospheric walk that combines storytelling with visits to some of the island’s most haunted and quirky pubs. The tour is led by a live guide who’s knowledgeable about the island’s eerie past, and the pace is steady—enough to soak in the stories without feeling rushed.

You’ll start at the Key West Chamber of Commerce just across from Shots and Giggles at 201 Ann Street. From here, the journey into Key West’s haunted side begins. The guide’s stories are what really make this experience shine — they’re lively, well-researched, and often spiced with local legends and creepy anecdotes. Many reviews mention guides like Chris, who’s praised for being “super nice and very informative,” and making the tales come alive with enthusiasm.

Exploring the Haunted Bars and Historical Sites

Captain Tony’s Saloon

Your first stop is Captain Tony’s Saloon, a legendary spot known as one of the most eccentric bars in the city. Its decor is a bizarre mix of bras hanging from the ceiling, fake bodies beneath the floors, and a peculiar tree in the middle that’s said to have stained the ground with stories of victims. The stories here involve more than just drunken tales—it’s a place seeped in ghostly lore that adds a sense of mystery to your first drink.

More Great Tours Nearby

Wine-O Bar & Lounge

Next, you’ll head to Wine-O Bar & Lounge, located in La Cocha Hotel, the largest building in town. The building’s height makes it a prime candidate for tragic stories of suicides, and these tragedies are said to have left lingering spirits. The setting is intimate, perfect for soaking in the spooky stories while enjoying your beverage.

The Roost and Key West Theater

The tour continues to The Roost, known for some of the best cocktails in town. Nearby, you’ll see the Key West Theater, which was once a place where children’s screams might still be heard — a haunting echo of its past. The guide might also share stories about the Artist House, which is rumored to be haunted by a cursed doll, adding a creepy twist to your walk.

Dean-Lopez Funeral Home and Old Town Tavern

Other stops include the Dean-Lopez Funeral Home, once the site of a lover’s obsession gone wrong, and the Old Town Tavern & Beer Garden, where you might find the spirit of Ernest Hemingway himself hanging around since his Key West home is just down the street. The stories of obsession, curses, and famous ghosts add layers of intrigue and make each stop memorable.

What Makes This Tour Worth It

At $35 per person, the tour offers great value — especially considering you’re getting a themed walk through some of the most haunted places in Key West, all narrated by engaging guides. The two-hour duration is perfect for an evening activity, and the mix of history, ghost stories, and bar visits keeps things lively.

It’s also worth noting that the tour is wheelchair accessible and includes just the guide and your group—so it feels personal and friendly. No food or drinks are included, so plan to bring cash if you want to buy a drink at each stop. The stories are what stand out, with many reviewers praising the guides’ storytelling skills and their ability to make the tales come alive.

Real impressions from travelers highlight the guides’ expertise and the fun atmosphere:

• “Chris was amazing! Super nice and very informative,”
• “Very informative and fun,”
• “Great stories and pub stops!”
• “Our guide was great—fun and funny,”

This feedback suggests that the tour isn’t just about creepy tales but also about enjoying a relaxed, entertaining night out.

The Practical Details

The meeting point is right outside the Key West Chamber of Commerce on Ann Street, making it easy to find. The tour runs in the evening, so it’s ideal for winding down after a day of sightseeing. It’s recommended to wear comfortable shoes, bring water, insect repellent, and weather-appropriate clothing. Remember, you’ll need your passport or ID to enter the bars, as state law requires proof of legal drinking age.

The tour lasts about 2 hours, so it’s not overly long but enough to pack in plenty of stories and visits. Since alcohol isn’t included, you might want to budget a bit extra for drinks as you go.

Is This Tour Right for You?

If you enjoy ghost stories, historic pubs, and a laid-back walking pace, this tour is a good pick. It’s especially suited for those who want to combine some history and spooky tales with a social, fun evening. The stories are told with enthusiasm, making them engaging without feeling overly serious or scary.

However, if you’re not interested in drinking or ghost stories, or if you have mobility issues, this might not be your best choice. It’s an adult-oriented experience, with a focus on haunted bars and stories of tragedy.

It’s also a good fit for those who want a quick, memorable experience without committing to longer or more expensive tours. The price and duration make it accessible for many travelers, and the reviews show that it consistently delivers a fun, atmospheric night.

The Sum Up

The Key West Haunted Pub Crawl Walking Tour offers a unique way to experience the island’s eerie side. Combining storytelling with visits to some of the most haunted pubs and historic sites, it’s a fun, atmospheric evening activity. Guides like Chris make the experience engaging, and the stories of ghostly lovers, cursed dolls, and haunted bars add a layer of intrigue to your trip.

While it’s not a tour for everyone—particularly if you’re not into ghost stories or alcohol—those who enjoy a bit of history mixed with spooky tales will find it well worth the $35 price. It’s a relaxed, social way to see Key West’s darker corners and learn about its ghostly legends, all in just two hours.

If you’re after a fun, slightly spooky night out that’s rich in local color and storytelling, this tour should definitely be on your list.

FAQ

Is this tour suitable for children?
No, this tour is intended for guests over 21, mainly because it visits bars and involves alcohol.

How long does the tour last?
It runs for approximately 2 hours, making it a perfect short evening activity.

Where does the tour start?
The meeting point is across the street from Shots and Giggles at the Key West Chamber of Commerce on 201 Ann Street.

Are drinks included?
No, drinks and food are not included, so bring cash if you plan to buy something at the bars.

Is the tour accessible for wheelchair users?
Yes, the tour is wheelchair accessible.

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

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

What kind of stories will I hear?
You’ll hear about haunted pubs, tragic stories like suicides, cursed dolls, and possibly the spirit of Ernest Hemingway.

Is it a guided walk?
Absolutely, a live guide will share all the stories and lead you from bar to bar.

Would this tour suit someone interested in history?
Yes, it offers fascinating insights into Key West’s darker moments and ghostly legends.

In summary, this tour offers a relaxed, story-driven look at Key West’s haunted side with a social, fun vibe. Perfect for history buffs, ghost story lovers, or anyone wanting to add a spooky twist to their evening in the Keys.

You can check availability for your dates here: