Hidden Gems & Historic Secrets: Exclusive City Walk
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.
Reviews
Reviews and Rating (Tripadvisor)
5 stars
4 stars
Reviews by Tripadvisor travelers
Corrine_M, 12/11/2025 2:58:50 PM
This was an absolutely fantastic tour of downtown Charleston … a little over 2 hours and I felt like I walked away with a real understanding of the history and the culture of the city. It was an easy walk filled with a lot of stories an interesting anecdotes by a tour guide that is part of the city’s history. So glad we did this tour!
Ed_S, 12/10/2025 7:27:25 PM
Great time, this tour hits hidden spots we would have never found on our own, but also hits the big stuff too. Our tour guide was very knowledgeable and enthusiastic about all things Charleston. The tour did go over 20 minutes or so and it was nippy outside so keep in mind depending on time of year.
Gicela_C, 12/9/2025 12:31:04 PM
It was our first time visiting Charleston and joining this walking tour was a great way to learn the history that shaped the culture in this town. As a multi-generational Charlestonian, Bruce was amazing, extremely knowledgeable and filled with many insider insights. We had a fantastic time following Bruce along the small alleys, visiting private gardens and learning about the old and new Charleston.
jaime82m, 12/7/2025 8:03:50 PM
Capt Jim was amazing!! He was so full of knowledge, was kind & engaging and made the history so interesting. I'd pick him to be my your guide on any tour in any city.
Arnold M, 12/3/2025 7:29:25 PM
Bruce, a seventh-ganeration Charlestonian, is fascinating - and funny. We have taken this Back Alleys tour twice before with other guides from this tour company, and came back because we enjoyed them so much ('haint blue' anybody?). Bruce's tour provided a local's perspective of what it was - and is - like to live in Charleston. We learned new details of Charleston history to supplement the previous tours and also felt privileged to get an insider's view of the city and its culture. He has a wealth of stories that you wouldn't get anywhere else but from a seventh-generation insider. It seems like he was able to get us access to beautiful backyard gardens that only someone who knows the homeowner could provide. Would go again on his tour!
mrlissag2023, 12/1/2025 10:52:36 AM
Captain bob was a very nice guide. His knowledge is great but needs to focus on tour route. Gets easily distracted by everything, ball, ball, ball, squirrel. Not everything needs to be talked about. Spent 13 minutes talking about a commode. We did enjoy the tour but wish he spent more time talking about the alleyways.
W892BGmartinl, 11/30/2025 10:46:13 PM
Lots of great, interesting history covering a variety of topics. Our guide, Captain Bob, was really knowledgeable and had a good sense of humor. The group was a good size which made it easy to get around and ask questions.
Rodica_E, 11/27/2025 8:42:38 PM
Very interesting tour. History, beauty and life. Lovely two hours in downtown Charleston with lots of stories.
Ken_R, 11/23/2025 6:21:34 PM
My wife & I really enjoyed spending time learning about the history of Charleston. This was a great tour, reasonably priced & Coach Duggar was a great guide. Learned information that we never could have learned on our own.
Chris J, 11/23/2025 9:39:16 AM
Mark is a knowledgeable and entertaining guide. Perfect tour if you want to go off the beaten path and learn about the local history and architecture of Charleston.
- 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
Departure point
Please meet your tour guide on the North side of the Old Exchange Building where the benches are.Return details
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.Redemption
Meeting point: 122 E Bay St, Charleston, SC 29401, USA -Departure Location: North side of the Old Exchange and Provost Dungeon at 122 East Bay Street (corner of Gillon St and East Bay St) where there is a shade tree and a bench. -Please arrive 15 minutes prior to the start of the tour. All tours depart on time. -Tour departs within walking distance of the cruise port. -We recommend parking either behind the Old Exchange Building in the 4-hour metered spaces or in the public parking garage at 25 Prioleau St.24 hours before travel date - 100% refund
Less than 24 hours before travel date - 0% refund

















