Charleston Historical Walking Tour: Pirates, Patriots, and More
Overview
Available languages
1 hour 30 minutes
Mobile ticket
Our most popular and diverse tour, A Walk Through Charleston is a comprehensive overview of Charleston history through the centuries. Charleston was founded in 1670 and quickly developed into the most cosmopolitan seaport on the continent. Come walk with us and learn about bawdy taverns & pirates, heroic patriots, the grandeur of antebellum architecture, the devastation of the Civil War, and much more. History will come alive as we stroll through the historic streets and gardens of the “Holy City”
Additional Info
Travelers should have at least a moderate level of physical fitness
Child rate applies only when sharing with 2 paying adults
Children must be accompanied by an adult
Operates in all weather conditions, please dress appropriately
Cancellation Policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
What‘s Included
90-minute Walking Tour of Historic Charleston
See some of the Charleston sites that can only be accessed on foot
Professional Guide
Learn about bawdy taverns & pirates, heroic patriots, antebellum architecture, Civil War and More
Gratuities
What To Expect
Nathaniel Russell House
Located in Downtown Charleston near High Battery, the Nathaniel Russell House Museum, 51 Meeting Street, is widely recognized as one of America's most important neoclassical dwellings.
Old Exchange & Provost Dungeon
Completed in 1771 as the New Exchange and Customs House, recognized today as South Carolina's most historic building. Where Patriots were imprisoned, the Constitution was ratified and George Washington was entertained.
Options
Charleston Walking Tour
Reviews
47 reviews
Total reviews and rating from Viator & Tripadvisor
Charleston, Must do tour!
SandyP200,
Oct 16, 2025
- Review from Tripadvisor
5.00Benjamin was an excellent guide articulating loads of history and humorous stories about Charleston. We enjoyed every minute. He was also very helpful in directing us what to do next. We highly recommend this tour!
Benjamin Rocks!!!!
Patricia S,
Sep 13, 2025
- Review from Viator
5.00Our guide Benjamin was not just extremely knowledgeable but funny too! We could have spent all day with him. We will remember so many of his phrases and how he connected the dots of your interesting historical story. Benjamin took us down so many out of the way streets with a story to tell about each. It was a super engaging tour. We learned so much laughing along the way.
Excellent! 5 stars!
janasI7071LK,
Apr 9, 2025
- Review from Tripadvisor
5.00Absolutely fantastic! Can’t say enough good things about the walking tour. Our guide was super knowledgeable and had a ton of insights into the history of Charleston. He was entertaining and funny. This was the highlight of our trip to Charleston!
A must experience tour
Shawn A,
Mar 26, 2025
- Review from Viator
5.00The tour was amazing. We learned so much from Benjamin and he was engaging, funny and helped us imagine Charleston across different periods of American history. He provided insight into the people and places that made the city central to the political and economic life of Empire and the nascent Republic.
Fun and Informative
Wayne B,
Mar 5, 2025
- Review from Viator
5.00Benjamin was awesome — fun and knowledgeable. His local roots and advice about what to do in Charleston was very helpful.
Fun change of plans
Matt W,
Feb 22, 2025
- Review from Viator
5.00Excellent change of initial plan. We were going on a walking tour and Mother Nature didn't agree with our choice of tour! Below freezing with wind chill. @smittylovesbear (Ron Smith) provided for a great, warm tour. Matt & Kathy Fredericksburg, VA
Charleston walk
Doug P,
May 29, 2024
- Review from Tripadvisor
5.00Great guided walking tour. Al, the guide, was knowledgeable and shared great facts and stories. Walk was 2 hours and really provided a great first day experience to exploring Charleston
Fantastic Walking Tour
Jody P,
May 25, 2024
- Review from Viator
5.00Benjamin was an awesome tour guide! He brought so much historical knowledge and when mixed with a bit of his southern charm, it was perfect. My husband and I were visiting Charleston for the first time and we are thrilled we picked Pineapple Tours to learn more about its history & people. We learned so much! Benjamin tried his best to keep us in the shade as much as possible too which was so appreciated in the hot sunshine. We would definitely take another tour with this company & recommend it to anyone visiting this gorgeous city. So fun & entertaining.
Must Do Tour in Charleston
Queenbfteam,
Mar 31, 2024
- Review from Tripadvisor
5.00We booked a last minute Easter weekend walking tour with 3 adults, 2 teens, + a child, and even though it was short notice, the Pineapple Tour team accommodated us. Ben was fantastic! We learned so much about the history of Charleston, had lots of laughs, & he even suggested great lunch options for after our tour! If you’re in town, we highly suggest booking any of the incredible tours Pineapple has to offer!
Fun way to get acquainted with Charleston
heidibarnes,
Mar 20, 2024
- Review from Viator
5.00Our guide was great and had an obvious real love for Charleston. He was knowledgeable and fun, he even through in more architectural information once he knew we were interested in that.
From $35.00
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Operated by Pineapple Tour Group LLC