Charleston Prohibition Pub Crawl: Speakeasy Sagas Tour

Charleston's speakeasies never actually closed during Prohibition. They just moved behind locked doors.

Speakeasy Sagas is a two-hour guided pub crawl through Charleston that traces the city's hidden Prohibition-era past, from the U.S. Customs House to St. Philip's Church and two restored bars with rumored bootlegger connections. A live English-speaking guide leads small groups through the streets where federal agents and rumrunners once clashed, stopping at four venues where you can order cocktails on your own tab while hearing how Charleston's underground liquor trade thrived despite the 18th Amendment. Ages 21 and up only.

Step-by-step itinerary

Explore Charleston's Prohibition history

• Visit U.S. Customs House
• See St. Philip’s Church lookout
• Tour High Cotton building
• Stop at Rudy Royale bar

The experience

The tour starts at the U.S. Customs House, the federal stronghold where agents once fought to stop illegal liquor from flowing into Charleston. From there, the guide walks you through the docks and streets where bootleggers made their deals, explaining how the city's geography (its waterfront access and network of back alleys) made it a natural hub for rumrunners. St. Philip's Church comes next, a landmark most visitors know for its steeple and history, but on this tour it becomes something else: a rumored lookout point and meeting spot in Charleston's underground world, where sacred ground and forbidden spirits occupied the same block.

The crawl moves through High Cotton, a restored bank building in the Historic District that sits at the intersection of Charleston's wealth and its rebellion. The guide connects the building to Carry A. Nation, the temperance activist famous for storming saloons with a hatchet, and to the contradiction she represented: a city that preached sobriety while pouring drinks in backrooms. The final stop is Rudy Royale, where the modern Southern charm masks the speakeasy past. By the end, you've walked four blocks of Charleston's actual streets and heard how a city known for grace and tradition quietly resisted federal law for thirteen years.

Cocktails are on you at each stop, but the guide's stories are included. The tour runs two hours and stays on ground level throughout the Historic District, making it accessible to most walkers. Groups stay small enough that you can actually hear the guide over the bar noise, and the pace is built around stopping and talking, not rushing between venues.

What’s included

• A knowledgeable and entertaining live guide in English who leads you through Charleston's Prohibition-era streets and stories.
• stops at four hand-picked pubs with historical connections to bootleggers and speakeasies.
• access to the U.S. Customs House, St. Philip's Church, High Cotton, and Rudy Royale as you walk the Historic District.

Before you book

Days and timesEvery dayDeparts at 16:00

Book up to4h before

AgesAdult (21 and older) · Under 21: can't be booked

GroupUp to 12

Live guideEnglish

Meeting point and pickupNo hotel pickup: you go to the meeting point. Ends at a different place from where it starts.

Cancellation and refundsFree cancellation up to 24 h before the start. After that, no refund.It may be canceled due to bad weather or if the minimum number of travelers isn't reached. If that happens, you're offered another date or a refund.

Prices and times updated yesterday

Good to know

Low physical effortWheelchair accessible

Operated by Revelry Tours of Charleston

Is this one for you?The two-hour pace and ground-level route work for most walkers, but this tour is built around standing in bars and listening to stories, not moving quickly between landmarks. If you want a faster-paced walking tour or prefer to avoid bar environments, a different Charleston history tour may suit you better.

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Top questions

What happens if it rains?

It may be canceled due to bad weather. If that happens, you're offered another date or a refund. Free cancellation up to 24 h before the start.

What exactly happened in Charleston during Prohibition that makes this tour worth taking?

Charleston was a city that refused to stay dry. While the 18th Amendment outlawed alcohol nationwide from 1920 to 1933, the city's waterfront location, federal agents who looked the other way, and a culture that valued rebellion made it a bootlegger's paradise. Speakeasies operated openly behind locked doors, rumrunners used the docks, and the city's elite and working class alike kept the party going. This tour reveals that contradiction: Charleston's image as a refined Southern city masked a thriving underground liquor trade.

Do I have to drink alcohol to enjoy this pub crawl?

No. The tour is about the history and the stories, not the drinks. You'll stop at four hand-picked pubs where you can order whatever you want (cocktails, beer, soft drinks, coffee), or nothing at all. The guide leads the group through the same streets and shares the same Prohibition-era stories whether you're holding a drink or not. Drinks are not included in the tour price, so you pay only for what you order.

How much walking is involved in the two-hour tour?

The tour covers the Historic District on foot, moving between four stops over two hours. The pace is steady but not rushed. You'll spend time at each venue listening to the guide before moving to the next one. The route stays on ground level and is wheelchair accessible, so it's built for walkers of all fitness levels, not for speed.

Who leads the tour, and what language is it in?

A live guide in English leads the group through Charleston's Prohibition history. The guide is knowledgeable and entertaining, trained to tell the stories of bootleggers, federal agents, and the city's underground liquor trade in a way that brings the 1920s alive.

What's the age requirement for this pub crawl?

You must be 21 or older to join Speakeasy Sagas. This is a tour of bars and speakeasy history, and the age restriction applies to everyone on the group, regardless of whether they plan to drink.