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If your grandmother spent the 70s mastering the jet-set bohemian look—picking up caftans on Capri and making shell bangles on St. Barths—combing her attic trunks for treasure just may be your favorite past time. The giddy pleasure you get from nicking her gilded hand-me-downs? Much like wandering around Charleston, an enclave of easy elegance. Enlist your best friend, peruse our Charleston style guide on Pinterest, and pack your bags. It’s time for a jaunt to Charleston!

Charleston has an affinity for curious customs. Take, for instance, the peculiar postal identities of some downtown dwellings. The darling stationary showroom Mac & Murphy can be found at 74 ½ Cannon Street, while bite-sized Sugar Bakeshop is a hop away at 59 ½ Cannon Street. The “½” often means a historic kitchen or carriage house is tucked away on the property, but sometimes it is merely a flight of fancy! Meanwhile, Zero George gets its name from its capricious address: 0 George Street. Comprised of three historic residences and two carriage houses, and the property’s bemusing “zero” simply adds to the its charm. The 18 guest rooms are a collection of muted colors, natural linen fabrics, heart pine floors, and marble bathrooms, which earned a 2013 Best New Hotel nod from Travel + Leisure. Check in, hang your clothing in the armoire, and ask the concierge to point you in the direction of King Street.

Day 1: Light Lunch
Pause for a moment. Contemplate Audrey Hepburn-turned-Holly Golightly in an effortlessly chic black column dress as she alights from a taxi to casually window shop on 5th Avenue at dawn with a pastry in one hand and small coffee in the other. Could there be a more beguiling mix of high and lowbrow? That’s the vision we have every time someone mentions Caviar & Bananas, the cleverly named gourmet market located three blocks from your hotel. Try the Southern, a mix of speckled butter beans, assorted peas, fresh herbs, and arugula in a parmesan vinaigrette. Equally tasty is the Prohibition: lemon poached shrimp, roasted carrots, radishes, grape tomatoes, roasted macadamia nuts, and mixed greens tossed in a green goddess dressing.

Day 1: Time to Shop King Street
King Street, recently named on of the 10 Best Shopping Streets in America, is your next stop. We hope there is room in your suitcase for new treasures… Like the buttery soft leather goods dyed in decadent-looking jewel tones that will draw you into Campo Marzio. SoHo meets Southern Boho on the racks at Hampden Clothing, a fashion-forward boutique stocked with owner Stacy Smallwood’s personal selections from runways in Paris and New York. At Croghan’s Jewel Box, a glass case full of gleaming curios—a collection of vintage cameo brooches, golden lockets, and burnished sundries—await. Be sure to ask about the Goldbug Necklace, designed and sold exclusively at this local institution now run by the third generation of its founding family. Sight of Society Street means it is time for a slight detour. Nip into Christophe Artisan Chocolatier-Pâtissier to indulge in one divine bite—the lavender caramel truffle is our reigning favorite flavor. Next stop: the Charleston City Market, one of the oldest public markets in America. The selection of soft, seemingly weightless scarves at the Historic Charleston Foundation shop means you now have a fabulous travel accessory. Check out the Charleston Shoe Company and the Charleston Hat Shop as well.

Day 1: Dinner in a Garden
Take a cue from Charleston gal-cum-Vogue editor Alexandra Macon’s list of favorites and have dinner in the garden courtyard at Peninsula Grill. Flickering carriage lanterns and candles make for a fabulous al fresco setting. “Everyone in Charleston knows the food at Peninsula Grill is incredible,” writes Macon, “but the bar there also makes a mean martini.” One more tip: order the Peninsula Grill Ultimate Coconut Cake® for dessert. Trust us. After supper, soak up the nighttime skyline while sipping a nightcap beneath the stars at the Market Pavilion rooftop bar.

Start your day in the gaze of confection-colored antebellum mansions. Charleston is a repository for decorative arts and one of North America’s most architecturally significant destinations. Meander through the quiet South of Broad neighborhoods. Catch the scent of tea olive and hear the sound of garden fountains as you discover some of the city’s oldest dwellings. Snag a seat overlooking King Street at Kitchen 208 for breakfast with a people-watching view. The Bridge Runner yogurt and granola parfait has a Lowcountry twist—benne seeds. Or dive right into local flavors with The Lowcountry—eggs, cheddar grits, and bacon served with stewed tomatoes and okra.

Day 2: Picture Yourself Here
Waltz through unrivaled 18th century Charlestonian grandeur at the Nathaniel Russell House, where the exuberant wall colors are startling—particularly when you remember the home is more than two hundred years old. Love the unexpected peacock-esque pageantry? The oval dining room’s bright turquoise hue can go home with you. It’s part of the Colors of Historic Charleston Paint Palette. Be sure to  visit the museum’s lovely garden and take a moment to discover the joggling board (hint: it’s a long plank suspended between two rockers).

Day 2: Dinner on Upper King
Begin the evening with a mojito amid the blowfish lights at Coast Bar & Grill. The cocktail menu includes four award-winning mojito variations. Ask if bar manager John Aquino is around—he is a trip! Then head one block over to Hall’s Chophouse for dinner on upper King Street. At this family-owned steakhouse, the vibe is decidedly see-and-be-seen and the piano playing is live (when making a reservation, request a table near the front window). For a taste of classic Charleston, order She Crab soup to start. Then enjoy collard greens and pepperjack grits with a chop of your choice. Continue your evening fun at The Cocktail Club. The extensive selection of house-made infusions, rare spirits, and farm-to-shaker beverages is impressive enough, but the clever drink names are utterly charming. Do you want the Manilla Ice or the Hibiscus Kiss? Round out the night at Bay Street Biergarten, and brush elbows with a local crowd. Although the craft beer menu seemingly goes on for days, this new spot offers plenty of other beverage options. And even if beer is not your thing, try the beer-boiled peanuts!

Take today to slow down, unwind, and truly soak of the city’s splendor.

Day 3: Southern Allure
When colonists settled Charleston in 1680, an urban development plan called the Grand Model established an orderly grid of streets. It is fun to wander and discover but difficult to get lost in the historic district. Spend the morning pedaling past the city’s many charms with beach cruiser rentals from Affordabike Bicycle Shop.

Day 3: Say ahhhhh….
Rejuvenate and replenish amid the 14-foot vaulted ceilings, exposed beams, and rustic beauty of Wentworth Spa, the historic stables-turned-luxury spa located in the garden of the Wentworth Mansion. Opt for an Aromatic Scalp and Body Massage with lime and cedar wood essential oils vigorously applied to the scalp, neck, and shoulders followed by a full body massage restoring both body and mind. Then enjoy a Hydrating Wrap with a blend of rich cocoa butter, soothing shea butter, and warm oil. If you are really ready for a treat—opt for both!

Day 3: Kiss the Sky
See the Holy City skyline from the water with a harbor cruise aboard this 84-foot, three mast wooden Schooner Pride. Sail past historic landmarks, barrier islands and the longest cable-stay bridge in North America for this cruise through nation’s most picturesque harbors. As the sunsets on this blissful day, you’re visit to Charleston draws to a close… for now. We will—we are sure—see you again soon.

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