Charleston: Prohibition Pub Crawl & Speakeasy Stories Tour

Summary

Charleston’s wild side told through hidden bars, scandalous stories and laughter echoing down cobblestone streets

You’ll walk Charleston’s storied streets after dark with a local guide who knows every scandalous corner—from the Customs House to hidden bars like High Cotton and Rudy Royale. Hear wild tales of bootleggers and secret sips while sharing drinks with fellow travelers. By tour’s end, you’ll feel both part of history and in on something special.

★★★★★★★★★★

4.50

(191 reviews)

What’s the experience like?

I’ll admit it—I signed up for the Charleston Prohibition pub crawl mostly out of curiosity (and maybe a little for the cocktails). There’s something about this city at dusk, when the humidity sticks to your skin and the gas lamps flicker. Our guide, Marcus, had this way of weaving stories that made me feel like we were sneaking around with bootleggers instead of just following him down East Bay Street. First stop was the old Customs House—imposing even now. He pointed at the stone steps where federal agents once tried to keep the city dry. I could almost hear the echo of heavy boots and whispered deals. The air smelled faintly of salt and something sweet from a nearby bakery.

We wandered past St. Philip’s Church—Marcus called it “the Holy City’s most ironic lookout,” which made everyone laugh. He told us how folks would gather here not just to pray but to pass along secrets about hidden bottles and safe places to drink. I’d never thought about churches as part of Charleston’s rebellious side before. At one point, an older local nodded at us knowingly as we passed; I wondered if he had his own stories from family or friends who remembered those days.

The real surprise was High Cotton—a place I’d only ever walked by before. Inside, you can still see hints that it used to be a bank (vault doors, thick walls), but now it’s all polished wood and clinking glasses. Marcus mentioned Carry Nation storming saloons with her hatchet, which got a few raised eyebrows from our group—imagine that happening here today? My whiskey sour tasted sharper after that story, somehow more defiant. Rudy Royale was our last stop; by then, we were all swapping stories like old friends, even if most of mine were borrowed from Marcus or half-remembered from earlier in the night. The whole thing felt less like a tour and more like being let in on a secret club—one where the password is just showing up and listening.

I still think about how Charleston manages to hide so much beneath its polite surface—the laughter behind closed doors, the way people look out for each other even when they’re breaking rules together. If you’re looking for a night that feels both mischievous and oddly comforting, this Prohibition pub crawl is probably it.

2h

Step-by-step itinerary

Day 1 — Explore Charleston's Prohibition history

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

What’s included

Your evening includes walking historic Charleston streets with an entertaining local guide who shares true Prohibition-era tales at each stop; you’ll visit hand-picked pubs like High Cotton and Rudy Royale (drinks purchased separately), all while soaking up stories that linger longer than any cocktail.