There’s no better base camp from which to explore Charleston, South Carolina, a peninsula port city founded in 1670, than the Dewberry. Located on Marion Square, a 10-acre downtown park, the hotel is a mid-century modern jewel in a city best known for colonial mansions. It occupies a converted Jfk-era government building with a handsomely restored brick facade, and its spacious, woodpaneled lobby looks straight out of Mad Men. Be sure to snag a piña colada at the Citrus Club, on the rooftop terrace, the highest commercial perch in town. And for city cruising, make use of the hotel’s French-style touring bikes to navigate the live-oak and palmetto–laden historic core.
But first, breakfast. Charleston rises early, and Daps, on Ashley Avenue, is a welcome newcomer to the morning-dining lineup—and not just because it’s in the emerging cultural hub north of the Crosstown; Daps serves up one of the best stacks of pancakes in the South.
For shopping, you can’t beat Oobe Brand, a menswear staple on lower King Street that specializes in classic American cuts (field coats, fisherman sweaters, trim chinos, selvage denim) and is run by a pair of former Clemson University roommates. From there, it’s on to lunch at 167 Raw, a luxe seafood joint whose Nantucket roots mix perfectly with the fresh catch from local waters. The restaurant’s signature lobster roll is one New England import that locals have near unanimously embraced.
Offset the indulgence with an obligatory spin through White Point Garden—at the end of the Battery, a Civil War defensive seawall—which boasts views of Charleston Harbor. Wander the surrounding neighborhoods, to marvel at the 17th-century mansions and old-school row houses, before rounding out the day at Melfi’s, the pizzeria just opened by restaurateurs Brooks Reitz and Tim Mink of Leon’s and Little Jack’s fame. Head a few blocks down to Uptown Social for a nightcap. Along with rotating cocktail specials and local beers, the two-story New York City offshoot features live music and a rooftop bar—a rarity downtown.
Clockwise from above left: The crew downs oysters at luxe seafood spot 167 Raw; a stack at Daps; menswear staple Oobe Brand; drinks at the Dewberry; the live oaks of White Point Garden.