Speakeasy Sagas - Charleston Prohibition Pub Crawl

Step back into the shadows of the 1920s, when Charleston was a city of contradictions—charming on the surface, rebellious underneath. On the Speakeasy Sagas Pub Crawl, you’ll walk the very streets where bootleggers dodged federal agents, secret bars buzzed behind locked doors. During Prohibition, alcohol was outlawed—but in Charleston, the party never really stopped. This wasn’t just a city of Southern charm and steeples. It was a city of hidden rooms, rumrunners, and lawmen who conveniently looked the other way. From elegant society scandals to rowdy waterfront crime, this tour reveals the untold story of Charleston’s wild side. Along the way, stop at hand-picked pubs where you can enjoy your favorite modern cocktails (not included in tour price) in the Holy City with a refusal to stay dry.

1. 1

   U.S. Custom House

   24 min

   Step back into the roaring 1920s, when Charleston was a hotbed of bootleggers, speakeasies, and federal raids. On this spirited pub crawl, we’ll uncover the city’s wild Prohibition-era past—starting with the imposing U.S. Customs House, once a stronghold in the fight against illegal liquor. From whispered deals on the docks to hidden bottles behind bar counters, you’ll explore how Charleston danced around the law—and raised a glass anyway. Cheers to rebellion, rumrunners, and the city that never stayed dry.

2. 2

   Stop 2

   24 min

   While best known for its soaring steeple and sacred history, St. Philip’s Church played a quieter role during Prohibition—as a rumored lookout point and meeting spot in the Holy City’s underground world of bootleggers and backroom deals. Just steps from where the law preached temperance, locals whispered about hidden stashes and secret sips. In a city where sacred met scandal, St. Philip’s stood at the crossroads of faith, folklore, and forbidden spirits.

3. 3

   Stop 3

   20 min

   High Cotton, a beautifully restored former bank building in Charleston’s Historic District, is where elegance, wealth, and rebellion once collided. Named after the Southern phrase “living on high cotton,” this landmark reflects the prosperity of Charleston’s cotton-trade era and the lavish lifestyle of the city’s elite. But beneath the refined atmosphere lies a more controversial story. Local legend connects the building to the fiery temperance activist Carry A. Nation, famous for storming saloons with a hatchet during her crusade against alcohol in the early 1900s.

4. 4

   Stop 4

   20 min

   Rudy Royale reflects a spirited history but behind its modern Southern charm lies a connection to one of the most controversial periods in American history - Prohibition. During the era of the 18th Amendment, when the sale and production of alcohol became illegal across the United States from 1920 to 1933, Charleston’s bars and backrooms transformed into hidden speakeasies where liquor continued to flow despite federal law. Charleston remains a city that resisted quietly, celebrates loudly, and keeps its spirits full behind closed doors.

• Wheelchair accessible
• Suitable for all physical fitness levels
• Only for ages 21+

For a full refund, cancel at least 24 hours before the scheduled departure time.