Bay Street Bastards Pub Crawl Shared Tour in Charleston

If you’re curious about Charleston beyond its charming streets and historic sights, the Bay Street Bastards Pub Crawl offers a unique twist—combining history, storytelling, and a bit of true crime. While we’ve not done this tour ourselves, the experience seems to draw a good crowd with a solid 4.5-star rating, and plenty of travelers rave about their guides and the stories they hear. It’s a mix of dark tales from Charleston’s past and visits to some of its most interesting bars—which makes it a fun, slightly edgy way to spend an evening.

What we really like about this tour is how it mixes entertainment with education. The stories are unique, often hard to discover on your own, and the small group size (just six people) means you get a more personal experience. Plus, the stops include historic sites like the Old Exchange & Provost Dungeon, which tell tales of pirates, smugglers, and colonial criminals. However, some reviews mention that the storytelling can be hit or miss, and the bar visits are fewer than originally advertised, so it’s worth keeping expectations realistic.

This tour might not be for everyone. If you’re after a deep dive into Charleston’s history or prefer more of a lively party atmosphere, it could feel a bit surface-level. Also, since alcohol is not included, you’ll want to budget for drinks at your own expense. It’s best suited for those interested in history, true crime stories, and a bit of local flavor—and who enjoy small-group, immersive experiences rather than large, busy tours.

Overall, if you enjoy stories about criminals, historic pubs, and exploring Charleston’s more gritty past, this tour could be a perfect fit. It offers a relaxed pace, plenty of interesting tales, and the chance to see some of Charleston’s iconic bars while learning about its darker side.

Key Points

• Small Group Size: Only six people, ensuring a cozy, personalized experience.
• Unique Stories: Focuses on true crime, pirates, and Charleston’s shadowy past.
• Historic Venues: Stops include places like the U.S. Custom House and Provost Dungeon.
• Cost-Effective: At $35 per person, it offers good value considering the stories and sites.
• Guide Quality: Tour guides are praised for their knowledge and storytelling skills.
• Evening Activity: Starts at 7:30 pm, ideal for a relaxed, after-dinner outing.

The Itinerary in Detail

U.S. Custom House – The Opening Act

The tour kicks off at the U.S. Custom House, a fitting starting point for tales of piracy, smuggling, and notorious crimes. The guide discusses some of the most infamous criminal cases in South Carolina’s history, from high-seas piracy to highway robberies. The stories are grisly but fascinating, and the setting—full of history—is a great way to set the tone for the evening.

One thing to note from reviews is that this first stop is free to enter, and the discussion lasts about 30 minutes. It’s a good introduction to Charleston’s criminal past, giving context to what you’ll hear at subsequent stops.

First Citizens Bank – The Mind of a Murderer?

Next, the group moves to the First Citizens Bank, where the talk shifts to what motivates people to commit murder. This stop invites you to think about whether past experiences or innate impulses are responsible for crimes. The guide asks questions like, “What pushes someone over the edge?” which makes the stories more engaging and thought-provoking. Expect another 30-minute stop with free entry, where the focus is on psychological insights and criminal motives.

Old Exchange & Provost Dungeon – Ghosts of Pirates and Outlaws

The third stop takes you below Charleston’s elegant buildings to the Provost Dungeon. This visit is particularly popular, as it’s a tangible glimpse into Charleston’s pirate and criminal underbelly. Historically, the dungeon housed pirates, smugglers, and colonial criminals, some of whom were part of Blackbeard’s crew. Prisoners waited in damp, shadowy cells, and the stories of punishment and lawlessness here are vivid.

This stop lasts about 30 minutes and provides a haunting look at Charleston’s gritty past. Several reviews mention how this part of the tour is especially atmospheric and well-researched, providing a real sense of the dangerous underworld that once thrived beneath the city’s polished surface.

Blind Tiger Pub – From Speakeasies to Outlaws

The final stop is at the Blind Tiger Pub, a bar steeped in history as a hidden speakeasy during Prohibition. Here, the focus shifts from the dark past to Charleston’s rebellious side, where bootlegging and backroom deals were common. The pub’s ambiance still echoes that secretive, law-defying era. Many mention that the pub is lively, and you can imagine outlaws and lawmen sharing drinks in the shadowy corners.

At this point, the tour lasts about 30 minutes, giving you time to enjoy a drink (not included) and soak up the historic atmosphere. Several reviews highlight that the guide’s storytelling here is engaging and that the bar’s history is a great backdrop for the tales of crime and defiance.

Who Will Love This Tour?

This experience is a natural fit for travelers who are interested in Charleston’s darker past, especially the stories of pirates, criminals, and lawmen. If you’re a fan of true crime, history buffs, or simply want a different way to explore the city’s story, you’ll probably find plenty to enjoy. The small-group setting makes it ideal for those who prefer a more intimate, personalized experience.

However, it’s important to remember that alcohol isn’t included, so budget accordingly if you plan to have drinks at each stop. Also, since the focus is on storytelling, some might find the pace a little slow or the stories lacking in detail, based on a few reviews.

The Value of This Tour

At $35, this tour offers a pretty good deal considering the stories and sites covered. The fact that the stops are at historic venues adds an educational layer that many generic pub crawls lack. Plus, the guide’s reputation for being knowledgeable and engaging enhances the overall experience.

Many reviewers mention that guides like Ken and Alex made the stories come alive, making the tour memorable. The reviews also highlight that the views and venues visited are worth the price, especially if you’re into Charleston’s history and nightlife.

Cancellation and Practical Info

The tour offers a full refund if canceled at least 24 hours in advance, which adds a layer of flexibility. It begins at 7:30 pm from the U.S. Custom House and ends at the Blind Tiger Pub. Expect the whole experience to last around 2 hours, with a maximum of 15 travelers—a good size for conversation but small enough to keep it personal.

Since this is an evening tour, the weather can influence the experience. If canceled due to bad weather, you’ll be offered a different date or a full refund. It’s suitable for ages 21 and over, so no kids allowed, and alcohol is on your own.

Frequently Asked Questions

Is this tour suitable for people under 21?
No, because it’s only for guests 21 and older, mainly due to the bar stops and alcohol consumption.

What’s included in the price?
The tour is $35 per person and includes a guide and stops at four historic venues, but alcoholic beverages are not included.

How long does the tour last?
It lasts about 2 hours, starting at 7:30 pm.

Are the stories suitable for all audiences?
The stories focus on crime, pirates, and lawlessness, which can be grisly but are generally suitable for adults interested in that kind of history.

Can I cancel if I change my mind?
Yes, you can cancel for a full refund if you do so at least 24 hours before the tour.

Will I visit all four bars/venues advertised?
Most reviews mention visiting three out of the four bars, and some found the storytelling lacking. So, expectations should be managed accordingly.

Is there a guide with extensive knowledge?
Yes, guides like Ken and Alex are praised for their storytelling skills and knowledge about Charleston’s past.

What should I wear?
Comfortable clothing and shoes; the tour involves walking and standing at each stop.

Can I buy drinks at the venues?
Yes, drinks are purchased separately at each stop, as they are not included in the price.

Is this tour good for history buffs?
Absolutely—if you love stories about pirates, outlaws, and Charleston’s criminal past, you’ll find plenty to enjoy.

Final Thoughts

The Bay Street Bastards Pub Crawl offers a lively, engaging way to explore Charleston’s darker side. If you enjoy stories about pirates, criminal masterminds, and lawless nights, this experience brings that past to life with a knowledgeable guide and atmospheric venues. It’s perfect for those who appreciate a mix of history, storytelling, and a good drink, all wrapped into a small-group adventure.

While some reviews note that storytelling can vary and the bar count might be fewer than expected, most agree that the experience is worth the price, especially thanks to the guides’ enthusiasm and the historical significance of each stop. It’s an ideal choice for adults who want an entertaining, slightly eerie glimpse into Charleston’s underworld—and who enjoy a relaxed, social evening.

If you’re in Charleston and want to see a different side of the city—one filled with ghostly tales and outlaw stories—this tour could be a highlight of your trip.

Remember: book in advance, arrive ready for some stories and a good time, and always have your ID with you. Cheers to uncovering Charleston’s secrets—one drink at a time.