A First-Timer’s Trip to Charleston

A couple walk down a plant-lined path

You’ve seen the many lists with Charleston rated as one of the country’s top destinations. You’ve read articles and heard friends rave about the restaurant scene, the historic houses and plantations, and the immaculately restored inns and new boutique hotels. And now you’ve decided it is long past time that you experience the city yourself. The extensive list of things that make Charleston such a popular destination, however, can also make it a little intimidating. Where to begin?

Josh Alexander, a luxury travel advisor at ProTravel and a member of the AFAR Travel Advisory Council, knows Charleston intimately from many visits and he is ready to help. He has created a four-day introduction that combines must-see sights with some of his own personal favorites. Don’t worry about trying to see it all, however. We’re confident that you’ll be back for more once you fall for Charleston’s charms.

A man playing saxophone


Gospel Brunch

Halls Chophouse’s Sunday gospel brunch has become a Charleston ritual, and tables are coveted, but Josh will make sure you have a reservation. You can dine on South Carolina favorites like shrimp and grits and biscuits and gravy, but the stars of the show are the gospel performers who will have you tapping your toes if not jumping to your feet.
Josh Alexander


Josh Alexander

With five years experience in the industry, Josh Alexander of Protravel specializes in luxury and exotic travel that is tailor made and bespoke for all budgets. He has strong relationships with hotels and tour operators, which allows him to gain value for his diverse clientele at top hotels in Canada and around the globe.
A man drives a carriage in front of a large arched gate.

DAY 1Arrive in Charleston

Among Josh’s top choices of places to stay are one that embraces the city’s long history and one of the hottest newcomers. The building that houses the 64-room Planters Inn, at the corner of Meeting and North Market, was built in 1844 and has been meticulously restored to reflect that moment in Charleston history. Antiques fill the common areas, rooms have four-poster beds, and carriage lanterns illuminate the popular Peninsula Grill’s courtyard at night.

As soon as you walk into the glass-walled lobby of the Dewberry, which opened in 2016, you’ll realize that this is a decidedly different, and contemporary, Charleston hotel. Guest rooms are elegantly understated, with floor-to-ceiling windows overlooking the city. Even with the hotel’s modern edge when it comes to its decor, you can expect an old-fashioned warm Southern welcome.

After checking in at the property of your choice, get the lay of the land with a bike ride, a walking tour, or a horse-drawn carriage ride through Charleston’s historic district. You’ll pass the colorful Rainbow Row, the Battery at the tip of the peninsula, and the stately homes south of Broad Street, among other sites. Have dinner tonight at 82 Queen, a restaurant that helped lead the renewed interest in Lowcountry cuisine when it opened in 1982. Ever since then it’s been serving signature Charleston dishes—Carolina crab cakes, fried green tomatoes, and she-crab soup. It’s located in three restored buildings, with 11 different dining rooms, all around a courtyard, where you can dine al fresco if you prefer.
An antique house with portraits on the walls

DAY 2History 101

Start your day with a hearty breakfast of shrimp and grits or the famous Charleston Nasty biscuit at Hominy Grill, a longtime local favorite that’s won national acclaim.

Next, head to one of the city’s prominent historic houses, the Aiken-Rhett House Museum, which was built around 1820 and meticulously restored to its 1840s condition. From its grand reception rooms to the kitchen and slave quarters, a visit to the house provides a look at the everyday lives of all of Charleston’s residents in the 19th century.

For lunch, Leon’s Fine Poultry & Oyster Shop announces its specialties in its name, but the menu also includes salads, catfish sandwiches, and avocado toasts. You’ll want to leave room for some soft-serve ice cream after your meal.

In the afternoon, set sail to see the Charleston skyline from the water. The SpiritLine Cruises excursion includes sights from Fort Sumter, where the first shots of the Civil War were fired in 1861, to the soaring Arthur Ravenel Jr. Bridge, which opened in 2005 and connects Charleston to Mount Pleasant, on the opposite side of the Cooper River.

Once you are back on dry land, prepare for an elegant night out with dinner at one of the city’s top restaurants, the Charleston Grill at the Belmond Charleston Place. Chef Michelle Weaver has been at the helm of the restaurant for five years, preparing updated versions of classic Southern dishes, as well as international choices on a “Cosmopolitan” menu—ahi tuna in an aguachile sauce, Iberico ham with piquillo peppers, and sturgeon salad with cornmeal blinis.
A saxophonist plays while a man in a hat plays piano. They are in front of a brick wall with a painting

DAY 3Gospel and Ghosts

If you’re in town on a Sunday, the most coveted tables for brunch are at Halls Chophouse, but Josh will make sure you get a reservation. At the family-owned and operated steakhouse, Sunday brunch is paired with joyous song. While the popovers, crab benedict, and, of course, the steaks are standout dishes, it’s the gospel performers who steal the show.

Spend the afternoon exploring one of Charleston’s plantations. Each has its particular appeals: the gardens at Middleton Place are historic and legendary; Boone Hall features the much-photographed Avenue of Oaks and also does an excellent job introducing visitors to Gullah culture; and Magnolia Plantation offers opportunities for wildlife sightings in its wetlands. Drayton Hall, however, is unique for eschewing every modern convenience. The Georgian-Palladian home has been conserved, rather than restored, and its state of suspended decay creates an evocative atmosphere. It’s easy to feel like its original residents may join your tour at any moment.

Sean Brock is one of Charleston’s most celebrated chefs, beloved by diners for the delicious dishes he prepares and by local farmers for being a passionate advocate for farm-to-table cooking. Tonight you’ll have the chance to experience what his approach to cooking is all about. The menu at Husk, on Queen Street, features the produce of Lowcountry farms and the catches of local fishermen. The menu changes daily, but you can expect a mix of Southern classics as well as the occasional international dish that incorporates fresh South Carolina ingredients.
Three people ride bikes down the beach

DAY 4A Day at the Beach

Pack up early this morning, but keep your swimsuit handy, as you’ll head to the seaside before you start your journey home. Several different beach communities are near Charleston. Folly Beach is a lively choice, with food trucks and beachside bars, and a festive feel. Isle of Palms is a popular family destination with miles of beach waiting for sandcastle builders to arrive. Kiawah Island, Seabrook, and Sullivan’s Island are quieter destinations where you can find yourself alone with the dunes and the crashing surf.

Have a late lunch on Sullivan’s Island, where Home Team BBQ is one of Josh’s favorite places for a barbeque meal. The menu includes dry-rubbed chicken, pulled pork, salt-and-pepper brisket, and other local specialties. It’s a fitting end to your first, but surely not last, visit to Charleston. If you think that more than one day at the beach is essential—we do—ask Josh about extending your visit to Charleston with several nights at Kiawah Island Golf Resort, a 10,000-acre barrier island that is home to a resort with an amazing beach and world-class golf and tennis facilities.