Available languages
2 hours
Mobile ticket
Explore some of Charleston's enchanting alleyways and historic sites on this small group, 2-hour walking tour. With our small group tours, you are guaranteed a more intimate and up-close experience. Charleston's alleyways are fortunately located within the popular historic district which allows us to include some well known points of interest and go a little "off the beaten path” while exploring the history and beauty of Charleston's enchanting alleyways. Generally, we include between four to six different alleyways/passages as well as popular points of interest like Rainbow Row and of course, tons of history! These pedestrian passageways are often overlooked, but walking along these cobbled paths is an opportunity to appreciate Charleston's rich history and hidden, more intimate charms.
Infants and small children can ride in a pram or stroller
Service animals allowed
Public transportation options are available nearby
Suitable for all physical fitness levels
Children must be accompanied by an adult
Operates in all weather conditions, please dress appropriately
Water bottle recommended
Comfortable shoes recommended
For a full refund, cancel at least 24 hours before the scheduled departure time.
Learn about the history and events that shaped Charleston
Professional and Licensed Local Guide
Stroll through the quaint and charming streets of the historic district
Explore several alleys and popular points of interest like Rainbow Row
Small-Group for a more personalized experience
Alleyways & Historic Sites Guided Walking Tour of Charleston
Go "off the beaten path" and explore the history and beauty of Charleston's enchanting alleyways
Gratuities
Old Exchange & Provost Dungeon
The tour will begin from the Old Exchange & Provost Dungeon. Please note that we do not go inside the building.
We will explore between 4 to 6 alleyways as well as popular points of interest, some of which are located in the residential parts of the historic district we call "South of Broad".
Come explore some of Charleston's most enchanting alleys and hidden passages on this small group tour. This tour departs from the Old Exchange and Provost Dungeon!
2,291 reviews
Total reviews and rating from Viator & Tripadvisor
Debbie D,
Nov 13, 2025
- Review from Viator
Very informative and interesting. Mark was extremely knowledgeable and passionate about the subject matter along with entertaining
P9990YEkarenh,
Nov 13, 2025
- Review from Tripadvisor
This tour was interesting but very limited. Our tour guide was very knowledgeable as he is a 5th generation Charlestonian. I felt like it was a tour of our guide's personal family history, instead of a broader Charleston history. He had a personal connection to every place we visited, many of which were of no historical significance. I had expected to be shown more Alleyways and Historic Sites.
Jane S,
Nov 12, 2025
- Review from Viator
Great glimpse into what it has been like to live in Charleston since its founding. Not just a recitation of dates and names. Highly recommended.
SARAH K,
Nov 11, 2025
- Review from Viator
My husband and I thoroughly enjoyed this tour. Duggar took us to so many picturesque, hidden corners of the city, but we also stopped at some more well-known spots. When you visit a city like Charleston, having someone who can provide historical context makes it a richer, more memorable experience. We took the tour on day one of our stay, which helped us get our bearings for the rest of the trip. We also purposely revisited some of the points on the tour independently. I got some great pics!

Kathie B,
Nov 11, 2025
- Review from Viator
It was wonderful and our guide was very knowledgeable. We learned a lot about the history of Charleston. We would highly recommend this tour.
Kevin D,
Nov 11, 2025
- Review from Viator
It was an easy walk; guide was friendly and knowledgeable; small group was enjoyable; Lovely day!!!!
Lauren M,
Nov 10, 2025
- Review from Tripadvisor
Bruce’s tour was terrific, providing us with historical information as well as wonderful anecdotes that came from a lifetime spent in Charleston. Highly recommend!

caroleo917,
Nov 10, 2025
- Review from Tripadvisor
Wonderful tour! Duggar was the perfect guide - informative, knowledgeable, and personable. Would highly recommend this tour especially on a first visit to Charleston.
Jeffrey A,
Nov 9, 2025
- Review from Viator
Mark has a deeply informed and entertaining perspective on Charleston, and his tour is a delight. It was truly memorable.
Ellen C,
Nov 9, 2025
- Review from Viator
Captain Bob was a well informed, knowledgeable guide who was both entertaining and thoughtful! Great tour enjoyed by all.
Operated by Lowcountry Walking Tours