Charleston Speakeasy Sagas 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 in the Holy City with a refusal to stay dry.

If you have 10 or more guests in one group, please get in touch with the private & group sales coordinator with Ghost City Tours.

Meeting Point

United States Custom House

200 E Bay St, Charleston, SC 29401, USA

Your guide will be waiting for you on the steps of the U.S. Custom House, on the East Bay Street side. Please note that this is the back entrance of the Custom House.

What's included:

• A knowledgeable and entertaining tour guide

Not included:

• Gratuities
• Only for guests age 21+

What to expect:

Duration: 2 hours

U.S. Custom House

200 E Bay St, Charleston, 29401-2611, South Carolina

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.

24 minutes

Old Exchange & Provost Dungeon

122 E Bay St, , Charleston, 29401-2103, South Carolina

Trace the secret history of speakeasies, smugglers, and the brave (or corrupt) souls who defied the dry laws. The Old Exchange and Provost Dungeon, once a colonial prison and later a hot spot for Prohibition-era crackdowns. From hidden booze to underground deals, and the law was just a suggestion.

24 minutes

St. Philip's Church

142 Church St, Charleston, SC 29401, USA

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.

24 minutes

Dock Street Theater

135 Church St, , Charleston, 29401-2899, South Carolina

The Dock Street Theatre has always been a place of performance and intrigue—and during Prohibition, the drama didn’t end with the curtain call. Behind the scenes, it’s said the theater hosted secret soirees and hush-hush cocktail hours, drawing Charleston’s elite to drink in defiance of the law.

24 minutes

Philadelphia Alley

Charleston, South Carolina

Philadelphia Alley is one of Charleston’s most storied and shadowy paths. Known for its bloody duels and ghostly legends, it also played a quieter role during Prohibition—a favored route for bootleggers and bar-goers slipping between speakeasies. By day, it was a historic footpath; by night, a hidden artery for forbidden spirits.

24 minutes