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.

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.

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.

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.

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.