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  • Languages Offered: English
Your tour begins at 8pm when you meet your guide on Anson Street, who over the course of 90 minutes, will take you on an uncensored journey of Charleston's sordid past. Hear the tales of brothels, corruption, prostitutes, scandals, and crime, and learn the city's darker secrets that other tours leave out.

While pastel-colored homes, sunshine, and southern hospitality reign supreme in the coastal city, it isn't always champagne and mimosas down here on the Charleston streets. From centuries ago to the present day, Charleston has been a place where high society is riddled with scandal, temptation, sin, and truly unruly behavior. 

Whether it’s a fascinating story about a legendary brothel, or a look back at ancient forms of punishment, find out what really went on in the streets in the "Holy City" of Charleston. Did Charleston have a red-light district? Why did prostitutes wear red shoes? Your licensed and experienced tour guides will answer these questions throughout the tour, and there really isn't any other Charleston walking tour like it.
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Bulldog Tours
See Charleston through a darker lens on this 90-minute walking tour of the Holy City’s most notorious locations. With an expert guide, learn about the debauchery that lies beneath Charleston’s polished surface. Hear about brothels, scandals, criminals and other wayward behavior as night falls on the city. A great uncensored tour for mature audiences only.
  • 90-minute evening walking tour of Charleston
  • Learn about the sordid and scandalized underbelly of the Holy City
  • Explore historically "seedy" locations with an informative guide
  • Be entertained by stories of raucous brothels and misbehavior
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1 - 5 of 16 reviews
Reviewed 2 July 2018
Lots of fun!

David C was a great tour guide, he was very knowledgeable and very aware of everyone in his group. He had us laughing and shivering at his stories. I hope he’s our guide on the next tour we go on. I highly recommend his tour...More

Thank April C
Reviewed 24 May 2018 via mobile
Dark Side Tour

Braxton Williams kept us laughing, entertained and interested from the beginning to the end of this tour. Interesting history, funny stories and great projection, we could hear every word! This was by far the best tour we took on our trip. Try it you won’t...More

Thank Janet B
Reviewed 6 May 2018
Great experience

Interesting and informative tour, our tour guide was very knowledgeable and a great story teller. Definitely glad we chose this tour!

Thank Kelly D
Reviewed 12 April 2018 via mobile
Fun time

Was a last minute decision to do this tour. Was a good history story that you wont read in the history books. Gordon did a great job, and kept you interested with his facts!!!

Thank krfields03
Reviewed 12 April 2018

It was interesting to hear about a different side of Charleston. Gordon, our guide, was very knowledgeable about the city and it's history. He was a good story teller with a decent sense of humor.

Thank FranknShawn
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