Speakeasy Sagas – Charleston Prohibition Pub Crawl

Introducing the Charleston Prohibition Pub Crawl

If you’re curious about how Charleston’s lively spirits survived during Prohibition, this tour offers a fun and informative peek behind the city’s legal curtains. The Speakeasy Sagas tour is designed for those who love a good story, history, and a taste of Charleston’s rebellious past—all with a side of social atmosphere.

What makes this experience stand out for us is the combination of knowledgeable guides and the authentic ambiance of historic sites. You’ll get not just a walking tour, but a vivid picture of what life was like in Charleston during the 1920s, with stories that bring the era alive. Plus, the chance to stop at some of Charleston’s prime pubs adds a lively, social touch.

One thing to keep in mind is that this tour is strictly for guests aged 21 and over, and alcohol isn’t included in the ticket price. While the tour itself is a great value at only $35, the cost of drinks is separate, which can add up if you plan to sample at each stop. This tour is best suited for those with an interest in history, a sense of humor, and a desire to see some of Charleston’s iconic landmarks in a fun, relaxed group.

Key Points

• The tour offers a balanced mix of history, storytelling, and social stops.
• Small groups (up to 15 participants) foster a personalized experience.
• It’s a two-hour walk covering notable landmarks and hidden corners.
• Expect entertaining guides with a passion for Charleston’s Prohibition past.
• The tour does not include drinks, but stops at several pubs offer opportunities to purchase them.
• The start and end points are well-chosen, with easy access from central Charleston.

A Deep Dive into the Speakeasy Sagas Experience

How the Tour Begins — The U.S. Custom House

Your journey kicks off at the U.S. Custom House on East Bay Street. This imposing building once played a crucial role in Charleston’s fight against illegal liquor, making it a fitting starting point. From here, you’ll step back into the roaring 1920s, where bootleggers thrived and federal agents made raids. Our sources tell us that this spot offers a glimpse into Charleston’s efforts to control and profit from the illicit alcohol trade, setting the tone for the tour’s lively storytelling.

While the tour is only about 24 minutes here, it’s packed with fascinating tales of whispered deals and hidden bottles. Expect to hear about Charleston’s unique role during Prohibition—stories that really bring the era to life.

The Old Exchange & Provost Dungeon

Moving on to the historic Old Exchange and Provost Dungeon, the tour continues to unravel Charleston’s clandestine activities. Once a colonial prison, this site later became a hotbed for illegal activity during Prohibition. Guides often share stories of underground deals, secret hideouts, and law enforcement crackdowns, making it a favorite among history buffs.

According to reviews, this stop helps visitors understand how deeply embedded the bootlegging scene was in Charleston. One reviewer noted, “We learned a surprising amount of history about Charleston and US history around prohibition,” showing how the tour balances local and national stories.

St. Philip’s Church — Sacred, Yet Slightly Subversive

Next, you’ll visit St. Philip’s Church, a well-known Charleston landmark with a soaring steeple. While primarily a sacred site, it’s rumored that during Prohibition, the church played a quieter role in the underground scene—serving as a lookout point or meeting spot for bootleggers and their allies. This juxtaposition of faith and scandal makes for a compelling story, adding depth to the tour’s narrative.

Guests often mention that this stop offers a surprising perspective—how even places of worship weren’t immune to the era’s clandestine dealings. One reviewer noted, “In a city where sacred met scandal, St. Philip’s stood at the crossroads of faith, folklore, and forbidden spirits.”

The Dock Street Theater — Dramatics Behind the Curtain

The historic Dock Street Theater adds an element of intrigue. Known for its performances and theatrical history, it’s also rumored that during Prohibition, secret gatherings and illegal cocktail parties took place behind its walls. Today, the theater’s historic charm makes it a compelling visual, and guides often share stories of Charleston’s elite defying the law in style.

While this stop doesn’t involve actual drinking, the stories certainly add a theatrical flavor to the tour, making it both entertaining and educational.

Philadelphia Alley — The Shadowy Passage

Your final stop is Philadelphia Alley, famous for its ghost stories and duels, but during Prohibition, it served as a discreet route for bootleggers slipping between speakeasies. Walking down this narrow alley, you can imagine how illicit spirits moved through the city’s shadows—another example of Charleston’s clever ways of bending the law.

Guests frequently praise the guide’s storytelling here, emphasizing the alley’s secretive vibe. One reviewer mentioned, “By night, it was a hidden artery for forbidden spirits,” capturing the allure of the alley’s history.

What to Expect During Your Tour

Guides & Group Size: Expect a small, intimate group capped at 15 (or 12, per updated info), which encourages a more personal connection. Our sources highlight that guides are knowledgeable and engaging, often blending humor with historical facts. Multiple reviews mention how guides like Jamie or Alex make the experience memorable through their storytelling.

Timing & Duration: The tour lasts approximately 2 hours—just enough time to see the key landmarks without feeling rushed. Each stop is around 24 minutes, giving ample time for photos, stories, and quick questions.

Cost & Value: Priced at $35 per person, plus the cost of drinks, this tour offers a solid value for anyone interested in Charleston’s history and vibrant past. Since drinks are not included, budget accordingly if you plan to indulge at each pub.

Accessibility & Age Restrictions: Designed for those aged 21 and over, participants should be prepared for some walking and standing. The tour is mostly outdoors or in historic sites, so dressing comfortably and wearable shoes are recommended.

The Social & Historical Atmosphere

The tour’s charm lies in the blend of lively storytelling and historic sites, making it more than just a walk. Our review sources mention that the small group size fosters interaction, and guides often share humorous anecdotes that break the ice.

Guests appreciate the informative yet fun nature of the tour. One reviewer wrote, “Jamie’s passion for history and storytelling made it such a fun experience,” highlighting the importance of a good guide in creating memorable moments.

How the Experience Feels

Expect to stand in front of historic buildings, listen to stories about Charleston’s bootlegging days, and peek into the city’s hidden corners. Although the tour doesn’t feature actual speakeasies—apart from the Vault—it captures the essence of the era through stories and nearby historic architecture.

The Practicalities

• Meeting point: U.S. Custom House, a prominent Charleston landmark.
• Ending point: The Blind Tiger Pub, a fitting spot to continue the night if you wish.
• Booking: Most travelers book about 15 days in advance, reflecting its popularity.
• Payments & Cancellation: Fully refundable if canceled 24 hours prior, making it a low-risk option.

Who Will Love This Tour?

This pub crawl is perfect for history enthusiasts who want a fun, relaxed way to learn about Charleston’s Prohibition past. It’s also a good fit for those interested in vibrant storytelling, historic landmarks, and a social atmosphere. If you’re curious about hidden Charleston or enjoy small-group tours with personalized attention, this experience hits the mark.

However, if you’re looking for a more party-heavy night with included drinks or extensive bar-hopping, you may find this tour a bit subdued. But for a mix of education and social fun, it offers an authentic slice of Charleston’s rebellious spirit.

The Sum Up

The Speakeasy Sagas Charleston Prohibition Pub Crawl offers a wonderfully balanced experience of history, scenery, and social storytelling. With knowledgeable guides leading small groups through key landmarks and hidden corners of the city, you gain a deeper appreciation for Charleston’s lively, defiant past. The tour’s modest cost makes it accessible, and the stories and views are well worth the time.

This experience is especially suited for curious travelers who enjoy a relaxed pace, historical narratives, and a touch of Charleston’s secretive charm. While drinks are extra, the tour provides a fantastic context for understanding the city’s colorful history and its enduring spirit of rebellion.

If you’re visiting Charleston and want an engaging, authentic, and intimate look at the Prohibition years, this tour could be a highlight of your trip.

FAQ

Is this tour suitable for people under 21?
No, this tour is only for guests aged 21 and over, as it involves alcohol purchases and discussions related to Prohibition.

How long does the tour last?
It lasts approximately 2 hours, covering several historic sites and landmarks.

Are drinks included in the tour price?
No, drinks are not included. You’ll have the opportunity to purchase beverages at the stops.

What is the group size?
A maximum of 12 (or 15, per info) travelers, ensuring a more personalized experience.

Where does the tour start and end?
It begins at the U.S. Custom House and ends at the Blind Tiger Pub, both centrally located in Charleston.

Can I cancel if my plans change?
Yes, full refunds are available if you cancel at least 24 hours before the tour.

Is the tour walkable?
Yes, it’s a walking tour covering key landmarks and hidden passages around Charleston’s historic downtown.

How do I book the tour?
Most travelers book about 15 days in advance through the provider’s official booking platform, securing your spot in this popular experience.