One of downtown Charleston’s best assets is its walkability. There’s plenty of joy to be had wandering on your own, with the fragrant floral air on your skin and the centuries-old cobblestones underfoot, but it’s far more illuminating to be led by a local. That’s especially true if your local has an affinity for the many stories hidden in plain sight. Unsurprisingly, the Holy City is home to a wide variety of tour companies, covering everything from haunted houses to pirate ships, with guides that help curious visitors dive deep into its history, architecture, and cuisine. Here are several walking tours of Charleston’s compact, scenic downtown for a variety of interests.
Bulldog Tours offers a variety of walking itineraries, including visits to restaurants that explain the development of Charleston’s cuisine across more than 300 years of history.
Courtesy of Bulldogs Tours
For the gourmand
Charleston is one of America’s dining hot spots, and with the wealth of restaurants here—everything from nationally acclaimed barbecue joints and oyster bars to French-inspired tasting menus and nouveau Chinese cuisine—it can be a tough to whittle down an eating and drinking to-do list. Fortunately, Bulldog Tours, one of the city’s longest-running operators, is here to help. Start with the 2.5-hour afternoon Savor the Flavors of Charleston Tour, which offers an introduction to Southern staples. You might sample she-crab soup and fried green tomatoes at 82 Queen, a speciality biscuit or hand pie at chef Vivian Howard’s Handy & Hot, and pulled pork sliders with coleslaw, collards, and cast iron cornbread at Poogan’s Porch.
Aside from showing you where to eat, Bulldog’s tours educate guests on the region’s complex history, through the lens of Lowcountry cuisine. “The enslaved contributed significantly to our traditions, preparations, and recipes, not to mention the associated labor with products like rice,” says company owner John LaVerne. “We hope that guests experience Charleston’s renowned hospitality while also learning about all the influences that have come together to put us on the world’s culinary stage.”
You might want something to accompany all those tasty bites, as well. If that’s the case, book Bulldog’s Toast of the Town Cocktail Tour, on which you’ll sip three adult beverages at three different lounges in the historic district, while guides share lesser-known stories about Charleston’s response to Prohibition (for example, the reason behind the red dots on local liquor store signs, and why cocktails were made using mini bottles until 2006). The groups are small (12 or fewer people), and by the end of the walk we’re guessing you’ll be ready to keep the party going with a collection of new friends.
For the design enthusiast
A walk along the tree-lined streets of Charleston’s South of Broad neighborhood—with its rows of pastel and brick homes adorned with intricate ironwork, breezy piazzas, and bright flower boxes—is essential for any first-time visitor. The nonprofit Historic Charleston Foundation has helped to protect the integrity of these buildings, and in the springtime many gracious homeowners welcome people in to see what’s behind those beautiful facades.
From March 13 to April 13, 2025, the Charleston Festival (formerly the Festival of Houses & Gardens) returns for its 77th year, offering tours of the opulent homes and gardens on these historic streets. A popular option is the Morning History Walks, which take place six days a week during the festival and are led by deeply knowledgeable locals. You’ll learn about the city’s history, going back to the antebellum period, and by the end of the walk you may be ready to start scanning Zillow listings.
Walk & Talk Charleston offers a wide range of topics, including one tour focused on pink houses.
Photo by Anna Zlotnicki
For the offbeat
When she left New York City more than a decade ago, Tyler Page Wright Friedman felt drawn to Charleston’s colorful homes and rich stories. The city reminded her of Bermuda, where her mother lived, and she dove into learning about it, becoming a guide and founding Walk & Talk Charleston.
Today, she and her company’s other guides relate some of the city’s most fascinating lore on a variety of special interest tours. Among the most popular is the two-hour History & Historic Gossip Tour through the heart of downtown Charleston’s historic district.“There are two quotes I love,” Friedman says. “From JFK: ‘All history is gossip.’ And from Mark Twain: ‘Never let the truth get in the way of a good story.’ There are so many characters and quirky stories in Charleston that come with a really deep and difficult history. I wondered, how do you get people to sign up for a history tour when you’re going to get into the nitty-gritty? I knew I had to also make it entertaining.”
Among the essential characters she discusses is Grace Peixotto, a Jewish woman who ran a brothel on Fulton Street and who was said to have had a longer funeral procession than pro-slavery Vice President John C. Calhoun. (Friedman admits that the latter part of the story has been debunked, but points out that the tale opens the door to important conversations about Charleston’s past.)
Looking for something even more colorful? Try Walk & Talk’s new Pink Houses Tour, which paints a near-complete picture of the city’s past and present through its pink buildings, showcasing its oldest residences, critical places to the LGBTQ+ community, and significant sites for Black history.
Frankly Charleston walking tours focus on Black history.
Courtesy of Frankly Charleston
For the historian
Speaking of Black history, this complex narrative is inextricable from the development of Charleston, but according to Franklin Williams, founder and sole tour guide at Frankly Charleston, most visitors aren’t getting the full story. A former charter bus driver who became familiar with the scripts of many tour operators in the 1990s and early 2000s, Williams learned firsthand how Charleston’s history was often being related in an incomplete fashion. He realized there was a great opportunity to help people better understand the city’s evolution, and whose hands and efforts really shaped this place. Since 2015, Williams has dedicated his company to showing visitors “the other Charleston.”
“There’s so much we don’t share with people,” Williams says. “We don’t talk about the artisans, we don’t talk about city slaves and their contribution to history and the culture. There’s more than what the average person gets.” Instead of touring well-known sites—the City Market and the plantations surrounding town—he shows groups “beneath the veneer” of popular centrally located residential areas like Radcliffeborough, Elliotborough, and Cannonborough. On his morning walking tours, Williams delivers a closer inspection of these places: their true origin stories, the contributions of the enslaved to building urban homes and neighborhoods, and how Jim Crow laws influenced life here in later decades.
“My tours are interactive,” Williams adds. “I want to hear more from guests than they hear from me. I like to enlighten people—to help them find a voice, to have uncomfortable conversations. If we don’t have these conversations with our friends and family, this history is going to go away.”
