Pressed for time in Charleston? Here's your ultimate list of must-sees and dos in a perfect three-day itinerary.
When it comes to popular destinations, Charleston’s hundreds of years of history, art, and architecture, coupled with an iconic culinary scene has transformed this Southern city into one of the most desirable year-round locales. There’s a lot of ground to cover and no shortage of things to do, and if you’re looking for the perfect three-day itinerary, we’ve got you covered.
Soak up Some History
Start your morning at Charleston City Market, where big, buttery breakfast biscuits and pimento cheese await at fan-favorite Callie’s Hot Little Biscuits. Home to dozens of vendors selling everything from local artwork and handicrafts, this historic market has been in operation since the 1790s and is a great place to pick up some locally crafted souvenirs. Don’t miss local artist Jonathan Green’s booth, which features an array of original paintings and prints.
Exit the market on Bay Street and spend some time exploring the galleries and shops around Charleston’s French Quarter before making your way over to the waterfront where it’s a requisite to snap a few pics at the Pineapple Fountain. From there, head south and pass the pastel-colored houses known as Rainbow Row along the way. Amble your way along the waterfront, or spend some time wandering the narrow alleyways and cobblestone streets South of Broad and see old antebellum-style homes and the most meticulous and beautiful southern gardens you’ve ever seen.
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If you’re looking to lean into some of the local history, Bulldog Tours offers some of the best historical walking tours in town. Before you head to lunch, it’s worth a quick visit to The Gibbes Museum of Art, which is home to more than 10,000 pieces of artwork in a beautiful Beaux Arts building just off Meeting Street.
It’s been a power-packed morning of sightseeing, and you’ve more than earned a break. Not far from the Gibbes Museum, 167 Raw Oyster Bar offers some of the city’s best lobster rolls and fish tacos. For a leisurely lunch of elevated French fare, Chez Nous is a pint-sized restaurant that changes daily and is a special spot ideal for couples or smaller groups. For something on the more casual side, Basic Kitchen offers plenty of indoor seating as well as a back patio and is a great spot with a number of health-conscious and vegetarian-centric menu items. Otherwise, on the seventh floor of The Restoration Hotel, The Watch offers a mix of burgers, salads, and Lowcountry classics, including a skillet mac and cheese that is simply out of this world.
After lunch, it’s dealer’s choice. Take a stroll around upper King Street and walk through Marion Square Park before heading back to your hotel to freshen up for the night. Whenever you’re ready, head directly over to The Ordinary for happy hour and oysters to get the evening started in style.
Just in time for sunset, head to The Dewberry for rooftop cocktails at Citrus Club (don’t miss the Mai Tai) before making your way over to dinner at Halls Chophouse. This tried and true local steakhouse is ranked among the best restaurants in Charleston, and for good reason. Hall’s also hosts an epic Gospel Brunch every Sunday with live music.
End your night with drinks at the Champagne Bar or in the courtyard of Peninsula Grill. Cap off your night with a slice of the ultimate coconut cake for the absolute chef’s kiss of a perfect first day in Charleston.
Shop, Sail, and Savor
There’s more great food in Charleston than there is time to spare, and there’s no time to waste. Start your day today with a solid base of sweet and savory crepes at Queen Street Grocery. Of course, if you’re looking for something a bit heartier, the signature breakfast dishes at Palmetto Cafe at Charleston Place are second to none.
Walk it off and enjoy a little retail therapy as you worm your way along King Street. Home to dozens of boutiques, Croghan’s Jewel Box is a good place to start, thanks to its curated collection of high-end estate sale pieces that will set you back a pretty penny. Madison-Matthews linens and cotton dresses in a variety of fun prints and is a can’t-miss-for-all things pretty frocks that can only be found here. Speaking of pretty frocks, The Shop at Beau & Ro can’t help but spark joy. Finally, the Historic Charleston Foundation is home to a number of local treasures, from books written by local authors to Brackish feather bow ties and cufflinks.
Depending on the weather and your level of interest in Civil War history, Fort Sumter is just a ferry ride away and offers another vantage point from beautiful Charleston Harbor. There are also several Charleston Harbor Tours, and if the weather permits, spending the afternoon out on the water or joining a sunset sail is. Perfect for all ages, if you’re really looking for a hyperlocal activity, Casual Crabbing With Tia is a great way to learn how to cast a net, set bait, and trap crabs with Charleston local Tia Clark. Otherwise, if you’re in the mood for shark tooth and fossil hunting, Charleston Fossil Adventures runs tours to nearby sea islands throughout the year.
If boating isn’t your thing, there’s plenty to keep you busy on dry land, including a must-visit to The International African American Museum. Opened in 2023 along the waterfront and offers 12 permanent collections of works as well as an exhibition gallery that is not to be missed.
After you’ve had some time to unwind and get ready, head over to Zero George for pre-theatre drinks and maybe some caviar aperitifs on the patio. By far one of the most charming and elevated restaurant offerings in town, from there, it’s a quick walk to Charleston Gaillard Center, which is home to the city’s biggest productions, from ABBA tribute concerts to The Righteous Brothers and everything in between.
After the theater, catch a ride uptown, where its dealers choice between Leon’s Oyster Bar for chargrilled oysters and fried chicken or Little Jacks Tavern for burgers and comfort food. You can’t go wrong at either locally beloved spot, and hey, no judging if you end up going to both.
If you’re in the mood for some seafood, Chubby Fish is hands down one of the best spots in town. There are no reservations here, so be sure to get here early or, do as the locals do and put your name on the list and head to The Tippling House for a glass or two of wine while you wait.
End your night with a Gibson at The Den. A sexy new bar inside Emeline, drinks are strong, the vibes are good, and the music is always right on point.
Get out of Town
Today’s a good day to get out and explore the Lowcountry. Spend the morning in charming Mount Pleasant just over the Ravenel Bridge and don’t miss a chance to check out Pitt Street Pharmacy, whose soda fountain serves up the best floats in town. You might want to grab brunch on the patio at Post House Inn, a charming bed and breakfast with a wonderful neighborhood restaurant on the ground floor.
Depending on the weather, today might be a good day to check out Sullivan’s Island. About a 30-minute drive from downtown Charleston, Sullivans is a beautiful and low-key beach town that also happens to be home to several stand-out restaurants, including Italian and seafood at The Obstinate Daughter. Right next door, The Co-Op serves up ice cold frosé all day.
After the beach, head over to Sullivan’s Fish Camp for an early dinner and pineapple daiquiri before heading back to Charleston. It’s been a great visit, so it’s time to toast your time in the Holy City in style with drinks in The Backyard at Little Palm.
Related: The Best Day Trips From Charleston