Arts & Culture, Discovery, Featured, Sip & Savor

Your Essential Charleston Itinerary

As beautiful now as she was 350 years ago, Charleston is a perfect juxtaposition of centuries old charm and cultured sophistication. Shaped by the city’s two rivers, the Ashley and the Cooper, Charleston bristles with an energy and vibrancy reserved for only the finest cities in the world. Glorious weather shines down, while locals and visitors alike amble down narrow cobblestone streets in search of reluctant artists, boutique shops and the country’s best restaurants. Whether it’s your first visit or your tenth, it’s easy to be seduced by Charleston’s charm. Crowned the Number 1 City in the United States for the last ten years, read on for our essential Charleston guide.

The perfect trip to Charleston starts with cocktails al fresco. Rooftop bars are plentiful and the Clocktower Terrace is one of the few in town that offers a perch overlooking historic King Street. Sip a Belmond Breeze while you admire views of the city skyline. Then, set out in search of local delicacies. Oysters are a crowd-favorite and can be found on menus throughout the city. Two of our favorite spots for fresh seafood? The Ordinary and The Darling Oyster Bar, both located a few shorts blocks from Belmond Charleston Place

The next morning, set out at first light with a private trainer for a run over the Ravenel Bridge. See if you can spot Fort Sumter, where the first shots of the Civil War were fired, and the Sullivans Island lighthouse in the distance. After working up an appetite, head to Callie’s Hot Little Biscuit, for a true taste of the South. Located in the historic City Market, afterwards, peruse the sweetgrass baskets which have been made by hand according to Gullah Geeche traditions for years. Then, plan to wander away the morning exploring historic Charleston. Stop by Waterfront Park to see its famous Pineapple Fountain, walk past the candy-colored homes of Rainbow Row and then onto the Battery, where Antebellum mansions overlook Charleston harbor. Allow us to pack you a picnic lunch and sit a spell under the enormous oaks of White Point Gardens.

Continue your downtown adventure by spending the afternoon on one of the country’s most famous streets – King Street. Peppered with national labels, boutique shops, art galleries and antique stores also dot the shopping district. Peacock proud locals delight in showing their wares and sharing the unique stories behind their products with curious travelers. After shopping, take a rickshaw ride to upper King Street, where lively restaurants and bars await. One of our favorite ways to try all of Charleston’s mouthwatering cuisine? Create your own dine around experience. Start with drinks at the speak-easy like Cocktail Club, move on to appetizers at the farm-to-table eatery Macintosh and then sample the sophisticated pizzas and pastas from Indaco. If you aren’t ready to say goodnight, a nightcap at Halls Chophouse is in order. Their Sunday gospel brunch is also a Charleston classic, beloved by locals and visitors.  

A city surrounded by water, rise with the tide the next morning as dawn breaks over the Atlantic. Embrace the Lowcountry lifestyle, take a walk on the wild side, and uncover secret sea islands with Coastal Expeditions. Admire the sculpture-like branches of Boneyard Beach. Stroll along the maritime forest, gathering shells and spotting alligators and bottlenose dolphins. After a full day of exploration, relaxation is in order. Laze away the afternoon at our horizon-edge mineral pool or indulge in a signature spa treatment.

No trip to Charleston is complete without a cosmopolitan night on the town. Start with a cocktail and live music at the clubby Thoroughbred Club before indulging in some of the city’s finest fare at Charleston Grill. Perfectly paired wines complement the global cuisine while live jazz sets the tone for a vibrant night. After dinner, head to the Gin Joint, for a cozy cocktail in their 1920s-inspired setting. Then, wander hand in hand down cobblestone streets as gas lanterns flicker in the evening light. Then, end your Charleston adventure as the sunset casts pink and orange hues over the Ashley River. You may just spot a bottlenose dolphin while a local jazz artist serenades the setting sun on his trumpet. These are the precious moments through which memories are shaped, endearing Charleston to locals and visitors alike.