Your base in Charleston will be one of two new hotels, the Grand Bohemian Hotel or The Spectator Hotel.

The Grand Bohemian Hotel, part of Marriott’s Autograph Collection, is on Wentworth, just off of King Street. The 50-room hotel eschews the four-poster beds and vintage furniture found at many Charleston properties in favor of a bright, colorful, and dramatic decor. It has its own art gallery, and Eleve, a restaurant serving contemporary American cuisine with views of the skyline.

Two blocks away, the Spectator Hotel is another notable newcomer. The interiors are inspired by 1920s style, and rooms have private patios with views of the French Quarter—one of Charleston’s oldest neighborhoods—or the steeple of the historic St Philip’s Church.

Your first taste of Charleston comes courtesy of Poogan’s Porch, the city's oldest independent restaurant. While it is located in a Victorian house, the interpretations of classic Southern dishes are decidedly contemporary. It’s only a 10-minute walk down Meeting Street from the Grand Bohemian to Poogan’s Porch, yet John recommends dropping into some of the stores along the way.

After your meal, set out to explore historic Charleston. It’s about a mile and a half from White Point Garden, at the tip of the peninsula, to Marion Square, near the northern end of historic Charleston, making the area ideal for leisurely strolling. But if you would prefer a carriage or rickshaw tour or a bicycle rental, John can arrange it. (Also, if you are staying at the Spectator, the hotel provides complimentary use of their bicycles.)

Return to the Grand Bohemian for a personal wine-blending seminar. Even serious oenophiles will learn some new aspects of wine appreciation from the hotel’s sommeliers and you will end the 90-minute session with a bottle containing your own personal blend.

Tonight you will dine at Hall’s Chophouse on King Street. The restaurant has all you would hope for from an old-school steakhouse, starting with the clubby feel, paneled walls hung with vintage prints, and comfortable leather seats. The steaks are flown in from Chicago, while the she-crab soup and shrimp & grits on the menu are reminders you are in Charleston.

Start your day with the Chefs’ Kitchen Tour with Culinary Tours Of Charleston. You’ll go behind the scenes, and into the kitchens, with some of the chefs who have led the city’s culinary renaissance. On this three-hour tour, you’ll walk and dine—learning from top chefs as you eat your way through town, ending with artisanal pastries and coffee.

After a morning of grazing, you’ll be able to wait till later in the day to eat again. Head over to the Charleston City Market after your tour, where you can shop for both gourmet and craft gifts, including sweetgrass baskets. You can also stop into some of Charleston’s many historic churches as you explore the neighborhood.

In the late afternoon, head to Virginia’s on King for a southern supper. You’ll eat your fill of popular South Carolina dishes: boiled peanuts, tomato pie, chicken and dumplings, and crab cakes.

Today you’ll head out to Boone Hall Plantation in Mount Pleasant, roughly 20 minutes by car from your hotel, for the highlight of your trip, the annual Lowcountry Oyster Festival. This estate counts 738 acres and was founded in 1681 as a cotton plantation. You’ll have a chance to explore the house and grounds before joining the festival fun, showcasing oysters from South Carolina and Virginia along with live musical performances all day. Gloves and shucking knives are given away at the event, and you’ll soon get the hang of shucking oysters with the help of friendly, knowledgeable locals. Vendors sell local and imported beers and wines, and there are also a number of food trucks serving dishes besides oysters.

Have breakfast at your hotel or fit in a stop at Hominy Grill, one of Charleston’s go-to breakfast spots, before heading to the airport for your flight back home.