“History loves company” is a favorite Charleston saying, and when spending 72 hours in one of our favorite southern cities, expect sweeping plantations, ghost tours of storied landmarks, and a culinary scene that rivals most any urban outpost. Fusing a laidback coastal vibe with uptown sophistication, this intriguing city is defined by a decadent and delightful point of view. 

Day 1  

Kiawah Island Scenic Drive, Carriage Ride, & Top Tables  

Start your day with Palmetto Carriage Works for an insider’s tour into the heart of Charleston, during which you’ll learn historical tales and did-you-know city facts. Afterward, walk along The Battery, past Rainbow Row to Waterfront Park, and spot Charleston’s larger-than-life-sized pineapple (a sign of Southern hospitality) in fountain form.

Refuel with a casual lunch at Home Team BBQ, then it’s off to Halsey Institute of Contemporary Art at the College of Charleston School of the Arts. This multidisciplinary laboratory showcases the talent of innovative visual artists, emphasizing the historical, social, and cultural importance of modern-day art. Any visit to Charleston must include dinner at Magnolia’s, where upscale Southern cuisine awaits, including Fried Green Tomatoes, Charleston Crab Cakes, and Blue Crab Bisque — all complemented by southern-inspired cocktails.  

Day 2  

Art, Architecture, & Oysters

First up, visit the Gibbes Museum of Art. Discover 10,000-plus works of art among the museum’s permanent collection, in addition to annual rotating exhibitions. Next, experience the historic Nathaniel Russell House, constructed in 1808 and considered an important neoclassical structure. Don’t miss the joggling board (Charleston’s answer to the rocking chair) in the formal gardens — a uniquely Charleston invention. Happy hour today is at The Darling Oyster Bar. Expect vintage Charleston vibes in a 115-year-old storefront, where the raw bar is as enticing as the restaurant’s ambiance and King Street location.

Early afternoon is the ideal time for a brief walking tour of downtown Charleston with Two Sisters Tours — Mary Helen Dantzler and Therese Smythe are seventh-generation native Charlestonians whose family first arrived in the Lowcountry in 1793. Learn of their hometown knowledge and the city’s rich history, from abundant colonial days to the turbulent Civil War era. Finally, cap the day with an unforgettable tasting menu at Wild Common, which celebrates cuisine by James Beard Award 2021 Semi-Finalist Executive Chef Orlando Pagán.  

Day 3

Sailing, Boutique Hopping, & Theater

If a Saturday or Sunday, savor a tasty meal at High Cotton Brunch, which serves up some of the finest city cuisine. Then it’s off to favorite Charleston boutiques - including Rhodes, Juliska, Julep, Hampden, and Croghan’s.

Next, climb aboard the Schooner Pride for an unforgettable afternoon sail in Charleston Harbor. Tonight, it’s dinner and theater. Start your eve with artisan cocktails and coastal-inspired cuisine at Gingerline (opt for the colorful patio if weather permits), and then it’s off to 34 West Theater Company, known for inventive live theater written by the theater’s actors and designers. Until next time, Charleston!