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
Reviews by Tripadvisor travelers
Beth_C, 10/19/2025 11:35:14 AM
Captain Jim was outstanding. Engaging and knowledgeable and goes above and beyond to make the experience all that you want it to be.
jeffhM7523HF, 10/19/2025 10:09:50 AM
Great tour with Captain Jim. He was very knowledgeable and we saw things we wouldn't have. Our favorite tour while visiting Charleston.
sbyers79, 10/18/2025 7:11:56 PM
Captain Jim did an excellent job telling stories about the areas we explored. Very interesting insights!
Helen_U, 10/18/2025 9:55:12 AM
Off the beaten path walking tour. Nice change from regular walking tours. I would recommend this tour
Nikki_M, 10/17/2025 10:49:47 PM
Charleston was a port stop on our recent cruise. Hoping for a less touristy enrichment experience we booked the Hidden Alleyways & Historic Sites small group walking tour largely due to the small group description. We received reminder messages as well as a text from our guide, Duggar, the morning of our tour confirming the meeting location, what he would be wearing and his cell number if we needed to reach him. Duggar’s extensive knowledge and storytelling are what made the tour a solid 5-stars. We would love to participate in another tour with Duggar should our travels bring us back to Charlotte.
denisemaniscalco, 10/17/2025 12:10:39 PM
Really enjoyed our tour and guide. If you enjoy seeing the town neighborhood and houses, this is for you. Our guide had been in Charleston for 7 generations and was a wealth of knowledge. Always ready to answer any questions. Really fun.
Julie_S, 10/15/2025 9:38:09 AM
Very nice tour of many highlights of the city! Duggar was so interesting and informative, you could tell how much he loves Charleston and the people there!
MaryBeth_R, 10/15/2025 12:08:51 AM
Duggar was an excellent guide. He was very fun and interesting. Seemed. like all of the locals knew him.
Joanne_M, 10/14/2025 6:13:52 PM
Captain Jim is a fabulous tour guide! We learned a lot about the history of Charleston. He is not only extremely knowledgeable but funny too!
Alexander_M, 10/12/2025 11:55:47 AM
Our tour guide Bruce was great; extremely friendly, knowledgeable about the area (and seemed to know half the town), and interesting to learn from and listen to. Couldn't ask for a better tour!
- 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