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Dark Side of Charleston Walking Tour

  • 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
Dark Side of Charleston Walking Tour
From US$28.00
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  • Overview
  • What to Expect
  • Important Information
  • Reviews
  • Q&A
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Dark Side of Charleston Walking Tour
From US$28.00
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.
What to Expect
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.
Reviews (25)
1 - 5 of 23 reviews
Reviewed 18 October 2018
Not Really A Walking Tour But It's Cute

Charleston is SO small that you don't need to book a walking tour. But since I was a first time tourist, I figured I would do some touristy stuff. Three reasons why I chose this specific tour: 1. I don't believe in ghosts 2. It's...More

Date of experience: October 2018
1  Thank Susan N
Reviewed 17 October 2018
very disappointing

We had taken a Charleston Stroll walking tour earlier in the day with John and it was amazing. We were offered a 20% coupon if we wanted to take another tour so we decided to do a Dark Side of Charleston tour later that evening....More

Date of experience: October 2018
Thank mozdrilla
Reviewed 3 October 2018 via mobile
The untold history of the old south!

Zach, the tour guide was awesome! His knowledge and exuberance for Charleston made this tour memorable. If you are in Charleston and are limited on time, The Dark Side of Charleston tour is a must! Leave the youngsters home though!

Thank Karen D
Reviewed 25 September 2018
Great guide, great trip!

Carol was a fantastic guide for our tour! She was very knowledgeable about the history and good at incorporating the more R-rated elements. At the very beginning of the tour she told us that it was a raunchy history tour that would talk about brothels,...More

Date of experience: September 2018
Thank talkingoaktrees
Reviewed 16 September 2018
Great adult fun!

This is a great tour if you like the kind of history they leave out of textbooks. We were assigned to Carol as our guide and had a fantastic time! She is a great storyteller and has a great sense of humor. This is an...More

Date of experience: September 2018
Thank AsHammer
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