Speakeasy Sagas - Charleston Prohibition Pub Crawl

Highlights

Inclusions

Itinerary

1. 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 min

2. 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 min

3. 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.

   20 min

4. 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.

   20 min

Cancellation

Free cancellation up to 24 hours before the experience starts, for a full refund.

Reviews

Ratings come from 207 reviews collected by our booking partner. They are travellers' own words, in the order they were written — never reordered to flatter the experience.

Know before you go

How it compares in Charleston

• Its from-price is 36% below the median of the 319 experiences we list in Charleston.
• Its length is typical for the group.
• By number of reviews it ranks 63 of 319.
• The operator lists free cancellation on it.

About Charleston

Charleston is a South Carolina port city of pastel row houses, cobbled lanes, church steeples, Gullah culture and Lowcountry cooking.

Charleston was settled in 1670 and grew on a peninsula between the Ashley and Cooper rivers, and it is one of the best-preserved colonial-era cities in the United States. Rainbow Row, thirteen pastel Georgian houses on East Bay Street, is the best-known sight. The Battery, a seafront promenade with old cannon and oak-shaded White Point Garden, looks out to Fort Sumter, where the first shots of the Civil War were fired in 1861. The city is nicknamed the Holy City for its many church steeples.

Top-ranked sights in Charleston: Charleston City Market, Rainbow Row, Old Exchange & Provost Dungeon.

See all 319 experiences in Charleston