Charleston, South Carolina has become one of the most popular destinations in the United States for good reason. Lined with cobblestone streets and historic buildings, the southern city has no shortage of charm.
Anyone who visits it is sure to be won over by its incredible sights, award-winning restaurants and ever-expanding cultural offerings. To walk the rustic streets of Charleston is to truly transport yourself to a different era. Spend a weekend here exploring its intersection of history and modernity and you’ll be booking your next trip back in no time.
As always, check for travel restrictions and closures before planning your trip.
Friday: Walk in the Steps of History
Start your weekend in Charleston with a hearty meal at Millers All Day, a downtown eatery that, as the name suggests, serves breakfast all day. After eating your weight in southern classics like fluffy biscuits, grits and pancakes in the cozy dining room, head to the Charleston City Market, one of the oldest public markets in the United States and a must-visit spot on any trip to the city. There, you can meet local vendors, like Swamp Thang Crafts and Easterling Novels and Books, to shop local crafts and stock up on souvenirs
If you’re not still full from breakfast, stop by Queen Street Grocery for a quick crepe or sandwich, as you watch carriage tours go by. Or to continue your tour of the neighborhood’s historic architecture, stop by the Delaney Oyster House at Hotel Bella Grace to grab a quick bite at their renowned raw bar and learn a bit about the hotel’s 200 years of history.
Then, make your way to the Old Slave Mart Museum, Charleston’s oldest museum of African American history and the first museum on the history of slavery in America. The museum educates visitors about the past and is staffed by many people who can actually trace their personal history to people who were forced to work in the area.
Spend the rest of the afternoon exploring the French Quarter neighborhood, from the stunning Waterfront, to the only French Huguenot Church in the United States to Gibbes Museum of Art, focusing on American artists and, especially, work that helps tell the Charleston story.
Finish the evening with dinner at FIG, an innovative eatery that gets creative with seasonal ingredients — and remains a favorite even after 20 years since it was founded. And if you still have energy left after your eventful day, grab a “Certified Lover Boy” or “Vaxxed and Waxxed” drink at Cocktail Club, where the creativity is just as strong as the liquor.
Saturday: Architecture Perusing and Afternoon Cruising
For your second day in Charleston, head down to the South of Broad neighborhood, the southernmost area of the city. With sweeping views of the water, the tip of the peninsula has long been the most exclusive region in town, so you can spend the morning taking in gorgeous homes of the past and present.
Start with Rainbow Row, a street of brightly colored historic houses in the Georgian style. Then, explore the nearby Edmondston-Alston House, Heyward-Washington House and Nathaniel Russell House, all mansions that once belonged to the Charleston elite.
For lunch, make your way over to Husk, an award-winning restaurant in the historic district, where you can get Carolina catfish, a glass of bourbon and a little break from all the action. Spend the rest of the day seeing Charleston from the best place possible: the water. Hop on a boat tour and cruise around the harbor, as you take in important landmarks, like Castle Pinckney, Fort Sumter, Waterfront Park, The Battery and the Arthur Ravenel Jr. Bridge.
As the sun sets and you step back on dry land, find your way north for dinner at one of Charleston’s most iconic restaurants, Leon’s Oyster Shop. Located inside a retrofitted auto body shop, it’s known for fried chicken, an impressive raw bar and great champagne, but you can’t go wrong with anything on the menu.
Sunday: Great Views and Even Better Food
It’s your last day in Charleston and you deserve to start it off with something sweet, so head to Sugar Bakeshop in the Cannonborough/Elliotborough neighborhood. Try a cinnamon bun, crumb cake, raspberry lemon cupcake or peanut butter cookie. Walk around the area and pop your head into cool vintage shops and bookstores and grab a few goodies to remember your trip.
From here, cross the Arthur Ravenel Jr Bridge to Mount Pleasant, where you’ll be able to bike around the area, see some of the city’s most impressive views and look onto downtown Charleston from afar. Rent a bike from Holy Spokes, the city’s bike share program, and weave your way through the neighborhood.
Grab lunch at Page’s Okra Grill, a welcoming diner that serves up southern favorites, like a pimiento cheese-topped burger. After clearing your plate, check out some of the neighborhood’s sites, such as the picturesque Fisherman’s Dock in Shem Creek Park, a greenspace with a boardwalk and trails.
Finally, make your way back across the bridge and up to Charleston’s East Central area to have dinner at one of the city’s most famous restaurants, Rodney Scott’s BBQ. Owned by James-Beard-winning pitmaster Rodney Scott, this is thought to be the best barbecue in town and maybe even in the country. Order a ribeye sandwich or smokey pulled pork — don’t forget the mac and cheese and the cornbread.
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