Speakeasy Sagas – Charleston Prohibition Pub Crawl

The Speakeasy Sagas – Charleston Prohibition Pub Crawl offers a captivating dive into the city’s lively history of bootlegging and secret speakeasies. Priced at $35 per person, this approximately 2-hour tour is designed for adults 21 and over who want to combine history with fun bar-hopping. With a small group maximum of 12 to 15 people, the experience feels intimate and personalized, making it ideal for those seeking both education and entertainment in Charleston’s historic district.

This tour departs from the U.S. Custom House at 4:00 pm, and although it does not include alcoholic beverages, it promises visits to some of Charleston’s most iconic landmarks and vintage bars. Whether you’re a history enthusiast or simply curious about Charleston’s Prohibition era, this tour provides a lively and informative look at a tumultuous time in American history. However, it’s worth noting that some stops are more bar-focused than speakeasy-specific, which might influence expectations.

Key Points

• Price and Duration: At $35 per person and lasting about 2 hours, the tour offers a quick yet immersive experience.
• History and Landmarks: Explore U.S. Customs House, Old Exchange & Provost Dungeon, St. Philip’s Church, Dock Street Theater, and Philadelphia Alley.
• Guides and Group Size: Led by knowledgeable guides like Jaime and Dawn, with groups limited to 12-15 guests.
• What’s Included: A mobile ticket with entertainment and storytelling; alcoholic drinks are not included.
• Booking and Flexibility: Confirmations are immediate, with free cancellation up to 24 hours in advance.
• Tour Focus: Emphasizes Charleston’s Prohibition history, with visits to landmarks linked to secret activities, bootlegging, and rum-running.

Starting at the U.S. Custom House and Legally Fighting Illicit Liquor

The tour kicks off at the U.S. Custom House, a striking building that once played a key role in Charleston’s efforts against illegal alcohol during Prohibition. Here, guides introduce the lively 1920s scene, describing Charleston’s bootlegging activities, secret deals on the docks, and federal raids. The building’s imposing architecture lends a sense of history’s weight, setting the tone for a journey into Charleston’s rebellious spirit.

From this initial stop, the tour moves on to Old Exchange & Provost Dungeon, where the story of smuggling and underground dealings continues. This historic colonial prison once cracked down on Prohibition-era lawbreakers but also secretly sheltered alcohol and illicit activities. Visitors learn about the hidden nature of Charleston’s alcohol trade and how locals defied the dry laws.

Exploring St. Philip’s Church and Its Rumored Underground Role

The next stop is St. Philip’s Church, famous for its soaring steeple and religious history. During Prohibition, this church is rumored to have served as a lookout point and clandestine meeting spot for bootleggers and backroom deals. The contrast between the sacred site and its alleged secret role in Charleston’s underground world adds a layer of intrigue to the tour.

Just steps away, the Dock Street Theater reveals another facet of Charleston’s Prohibition era. This venue, known for performance and intrigue, supposedly hosted secret parties and hush-hush cocktail hours for Charleston’s elite. The mention of clandestine gatherings behind the theater’s historical facade gives the tour a glamorous twist.

Philadelphia Alley and Its Shadowy Connection to Bootlegging

A highlight of the tour is Philadelphia Alley, a narrow, historic passageway known for its violent duels and ghost legends. During Prohibition, this alley was a favored route for bootleggers and patrons slipping between speakeasies. By night, it became a clandestine pathway for forbidden spirits, adding a sense of mystery and thrill to the tour’s narrative.

This alley’s historical reputation as a place of secret activity makes it a gripping stop, especially given its legendary status in Charleston’s haunted lore. Visitors learn how such hidden routes facilitated Charleston’s lively underground drinking scene.

What Stops Are Included and What to Expect

The tour’s stops are carefully selected for their historical and cultural significance. The U.S. Customs House showcases the city’s fight against illegal liquor, while Old Exchange & Provost Dungeon reveals the clandestine world of speakeasies and smugglers. St. Philip’s Church provides a glimpse into the city’s religious and secretive sides, and Dock Street Theater offers a peek at entertainment venues hosting covert gatherings.

Philadelphia Alley wraps up the tour with its legendary reputation as a passage for bootleggers. Each stop lasts approximately 24 minutes, giving enough time to absorb the stories, take photos, and enjoy the atmosphere without feeling rushed.

The Role of Guides and Their Storytelling Style

Guides like Jaime and Dawn receive high praise for their knowledge, friendliness, and storytelling ability. Many reviews mention how guides answer questions openly, providing engaging narratives that blend fact with local lore. The guides’ enthusiasm helps bring Charleston’s Prohibition era to life, making history feel immediate and relevant.

Some guides are noted for their entertaining storytelling, often weaving in humorous anecdotes and background stories about each landmark. This approach makes the tour especially appealing to those who enjoy a lively, storytelling-driven experience.

The Reality of Bar Visits and Drink Inclusion

Although the tour emphasizes bar stops, it does not include alcoholic beverages, so guests should plan accordingly. Stops are at historic pubs and restaurants where drinks can be purchased if desired, but alcohol is not part of the tour package.

Some reviews note that the venues visited are more traditional bars than true speakeasies, and the atmosphere in certain locations can be loud, making hearing the guide’s commentary more challenging. A few participants feel the descriptions of the locations differ from their expectations of authentic speakeasies, as some stops are standard sports bars with interesting stories.

Group Size, Pacing, and Atmosphere

With a group size capped at 12 to 15 participants, the tour maintains an intimate and friendly vibe. This small group setting allows for easier interaction with the guide, who can answer questions and adapt the storytelling to the group’s interests.

The pace of the tour is brisk but comfortable, offering a good balance between sightseeing, storytelling, and socializing. The stops are spaced evenly, each lasting around 24 minutes, allowing enough time for exploration without dragging on.

Booking, Cancellation, and Practical Info

Reservations are typically made 15 days in advance, reflecting the tour’s popularity. The start point is at the U.S. Custom House, and the tour begins promptly at 4:00 pm. The mobile ticket simplifies check-in, and free cancellation is available up to 24 hours before the start.

Participants must be at least 21 years old to join, aligning with the tour’s focus on alcohol-related history. Since alcohol isn’t included, guests should budget for drinks at the stops if they choose to purchase any.

Who Will Enjoy this Charleston Prohibition Tour?

This tour appeals most to history buffs, architecture lovers, and those interested in Charleston’s colorful past. It combines cultural landmarks with lively storytelling, making it ideal for adults seeking an engaging, small-group experience. The focus on Prohibition-era stories offers a unique look at how Charleston’s residents defied the law, blending history and local legends.

Those expecting an authentic speakeasy experience with multiple cocktail bar visits may find some stops more conventional than anticipated, but the storytelling and landmark visits compensate for that. It’s especially suitable for visitors who enjoy combining walking tours with a bit of pub culture.

The Sum Up: A Fun and Informative Peek into Charleston’s Rebellious Spirit

The Speakeasy Sagas Charleston Prohibition Pub Crawl provides a lively, well-reviewed way to learn about Charleston’s defiant past during Prohibition. The $35 price tag includes visits to historic sites, engaging guides, and a small group atmosphere that makes the experience more personal.

While the tour emphasizes history and storytelling over actual speakeasy visits, it delivers a compelling narrative about Charleston’s underground activities and iconic landmarks. Perfect for history lovers and curious visitors, this tour offers a spirited glimpse into the city’s rebellious side, with plenty of stories to tell long after the walk ends.

If you’re interested in Charleston’s historic lore, enjoy small-group tours, and don’t mind paying for drinks separately, this experience makes a great addition to your city exploration.

Frequently Asked Questions

Are alcoholic drinks included in the tour?
No, the tour does not include drinks. Guests can purchase beverages at the stops if they wish, but alcohol is not part of the package.

Is this tour suitable for families?
No, this tour is only for guests aged 21 and over due to its focus on alcohol-related history and bar stops.

How long does the tour last?
The tour lasts approximately 2 hours, starting at 4:00 pm and covering several landmark stops in the historic district.

What should I expect at each stop?
You’ll visit historic sites like the U.S. Custom House, Old Exchange & Provost Dungeon, St. Philip’s Church, Dock Street Theater, and Philadelphia Alley, each offering stories related to Charleston’s Prohibition-era activities.

Can I cancel my booking?
Yes, bookings are fully cancellable free of charge up to 24 hours before the tour start time.

Who are the guides?
Guides such as Jamie and Dawn are praised for their expertise, friendliness, and engaging storytelling, making each stop memorable.

How many people are in the group?
The group size is limited to 12 to 15 guests, ensuring an intimate and interactive experience.

Where does the tour start and end?
It begins at the U.S. Custom House and concludes near Blind Tiger Pub on Broad Street, with the tour designed for easy access and walking.