Don’t let the slow Southern drawl of its residents fool you—the historic port city of Charleston has a refined culinary scene that is developing at a rapid pace, making it a hot spot for haute cuisine and winecentric bars.
Get a feel for Charleston’s historic charms by staying at an inn or bed and breakfast, like the Wentworth Mansion (149 Wentworth Street). Built in 1885, the mansion is appointed with working handcarved marble fireplaces, Tiffany stained glass windows and intricate woodwork. Reese Witherspoon spent her wedding night here with Ryan Philippe—and though the marriage didn’t last, the two-room Grand Mansion Suite retains its romantic allure, sweetened by nightly Madeira and Sherry service. For more modern amenities, including a rooftop pool, opt for the upscale Charleston Place Hotel (205 Meeting Street), located inside a luxurious shopping and dining complex.
A terrific way to take in the sights in one swoop is via (comically) narrated horse-drawn carriage; try Palmetto Carriage. On the trip, you’ll scope out Civil War-era mansions along the harbor, ride through the quaint, colorful French Quarter and cruise for handmade crafts, like weaved sweetgrass baskets (a tradition brought by African slaves to the Carolinas) at the City Market near Meeting Street, housing four blocks of open-air vendors of all types. If time allows, linger for a day on the lush grounds at a nearby plantation, like the grand Magnolia Plantation and Gardens.
If you’re thinking shrimp and grits is all you’ll find in Charleston—think again. Southern specialties get gourmet treatments at Circa 1886 (149 Wentworth Street), where the carriage house setting complements the exquisite regional cuisine of chef Marc Collins. Favorites include iron skillet-cooked pork chops with an applejack molasses cure. End the evening with a glass of wine at Bin 152 (152 King Street), a casual gem hidden among a handful of antique stores that offers 30 wines by the glass (all affordably priced between $7–15), charcuterie and cheese, along with vintage knickknacks.
For lunch, try Fleet Landing (186 Concord Street), a nautical-themed seafood joint perched over the water. Try the She-crab soup, fried green tomatoes and have a sweet tea cocktail (the signature drink down south). Don’t miss Charleston Place, with its luxury shops; the complex also houses the iconic Charleston Grill (224 King Street), offering a mix of French and Lowcountry dishes with some 1,300 wine selections and live jazz to boot.
Enjoy Charleston’s bustling bar scene at Social Wine Bar (188 East Bay St), which offers affordable tasting flights and a youthful, lively atmosphere (especially on Monday nights when happy hour prices rule) or take in the views from the swanky Pavilion Bar (225 East Bay Street) featuring mojitos, martinis, a Champagne menu and Southern specialties like spiked punch.
Taste Charleston’s trendy side at FIG (232 Meeting Street), showcasing seasonal ingredients in innovative dishes (like pork trotters with a farm-fresh sunny side up egg) and custom-made cocktails such as The Quincy (made with quince fruit syrup, Bourbon, lemon juice and Tuaca-soaked cherries).
A visit to Charleston wouldn’t be complete without a stop at the plush Peninsula Grill (112 N. Market Street). The sophisticated dining room and lovely outdoor garden make it the perfect choice for your finale dinner—providing a convenient excuse to wolf down the supersized, Southern-style seven-layer coconut cake. Nearly everyone leaves the restaurant with a doggie bag.