Art of the City, Charleston: How to Travel Like a Local in the Holy City

Charleston, South Carolina remains one of the most popular urban travel destinations in the world for good reason. But what should you do when you finally get to go? Here, we mix it up with locals and share some of their favorite things to do in Charleston.

The bells are ringing and folks are heading into church dressed in their Sunday best. I happen to be on the southern end of Marion Square named after South Carolina’s Francis Marion — an early advocate of the guerrilla warfare that won the American Revolutionary War, but also a slave owner who fought groups of freed slaves and led ruthless campaigns against the Cherokee. A block away from this monument representing the most idolized and reviled aspects of our history sits Emanuel African Methodist Episcopal.

“Those people are a lot stronger than I am,” says Darren referring to the congregation. Darren’s a Charleston transplant with gray-peppered hair who moved with his wife, a local, six years ago from Kansas City. “I don’t think I could’ve ever forgiven him.”

Walking by the church just before noon, there’s no apparent, lingering reminders of that horrific day, only the soft hum of service underway inside.

A Rare Commodity

The history of this town can be both charming and ugly with ghosts of the past lingering in the present. At the same time, Charleston is a rare commodity in the United States. Whereas so many other cities have retrofitted historic, walkable centers into wide thoroughfares and parking lots, Charleston has a legacy of historic preservation — and it’s drawing tourists in record numbers with magazines proclaiming it a top travel destination, not just in the United States, but worldwide.

Few casual observers will dispute that Charleston is looking good these days. The peninsula, indeed, is a treat to walk, especially on Second Sunday when King Street is blocked off to vehicular traffic. But what also can’t be disputed are the numbers. Charleston has changed drastically from a minority-majority city in 1980 (two-thirds black) to 73.2 percent white in 2017. The city’s historic black population has been moving to the suburbs in response to increasing rents pushed up by the influx of upscale restaurants, and yes, boutique hotels to help respond to the growing number of tourists visiting the city — 6.9 million in 2017, up from 5.44 million in 2016 and 5.15 million in 2015.

This blast of information isn’t meant to guilt you out of visiting Charleston. To the contrary, you should go, appreciate the city’s culture of preservation, and bring that appreciation back to your hometown to demand a more walkable city. But given certain realities, it’s especially important to travel respectfully here.

Maybe think twice about the carriage horse ride, derided by many locals as animal cruelty with looming questions over how well the animals really tolerate working in the 90-degree summer heat. Do splurge on that romantic night out, but also check out local stomping grounds like Jestine’s and Moe’s Crosstown. Pollution is a concern, too, with cruise ships damaging the water and air, so maybe think about coming in by train if you can. (Amtrak’s Palmetto line arrives at 10 a.m. and the Silver Meteor at 9:17 p.m.)

Charleston is and will remain a special place. It’s a city of good food, affable smiles, and palpable romanticism unlike anything else in the United States. Follow our list of things to do in Charleston, ranging from bars and restaurants to art museums, and parks and there’s no doubt you’ll be joining the choir.

Downtown Abbey goes Stateside at the Wentworth Mansion


“We try to differentiate ourselves by delivering the very best service,” says Richard Widman, founder of Charming Inns, a family-owned collection of historic inns in Charleston, including the Wentworth Mansion.  “You can have a beautiful property and it can be ruined by the staff.”

Indeed, that high-level of service has been recognized time and time again with the Wentworth Mansion winning trivago Awards honors in 2017 and 2018. Of course, the property itself wins guests over with its attention to detail. Italian crystal chandeliers greet you in the lobby with hand-carved marble fireplaces in the next room over where you can have a glass of wine in the afternoon with hors-d’oeuvres..

By the end of the stay, you’ll feel like Downtown Abbey came Stateside.

Wentworth Mansion

Top rated
10.0 Excellent (406 reviews)

Refined Lowcountry


There’s a sleek, modern ambiance to The Restoration, another trivago Award-winner on the corner of Wentworth and King streets stretched across five buildings. Exposed brick walls are a motif throughout the establishment from shared sitting areas to some of the guest rooms. You can sense that you’re in a reused space (because it is) that’s lived different lives since the building was first constructed.

Today, the property is firmly at home as a four-star luxury property with its Amethyst Spa & Nail Bar offerings and the rooftop view of the Holy City’s collection of steeples reaching out to the sky above. The Restoration set out for a refined look that blends the best of luxury and Lowcountry and they’ve done it in spades. Welcome to the New South.

Hotel The Restoration

Top rated
9.6 Excellent (2131 reviews)

Places to Eat in Charleston, SC

“One thing about Charleston,” says Omar, born and raised Charlestonian, “You will not go hungry.” This sentiment, the pride in the local cuisine, is shared across town.

“The culinary aspect has developed over the last 10 years with the Charleston Food and Wine Festival and James Beard chefs,” says Wentworth man, a longtime Charleston transplant from Cleveland. “I’d put our top five restaurants up against almost anywhere.”

Before You Leave The Hotel...

The highlight of a stay at the Wentworth Mansion might be the breakfast next door at Circa 1886 with Chef Marc Collins bringing to the table a healthy spin on classic Lowcountry cuisine. You can’t help by spoil yourself with some sweet breakfast pastries on the side of a breakfast frittata with asparagus, Monterey Jack Cheese, and mushrooms served with grits and applewood smoked bacon (or sausage)

Charleston Grill

The Charleston Grill, attached to the five-star Belmond Charleston Place, is the kind of place you visit for a special occasion. Come dressed in your Sunday best as you dive into one of the most celebrated restaurants in Charleston.

The Sturgeon, an import from the Pacific Northwest, is a staff favorite. But set yourself up for the seafood theme with an order of crab cakes with shrimp and half-sliced tomatoes in a lime-dill vinaigrette. Between bites, take a moment to enjoy the live music. One night might feature a guitar-violin duo, with a repertoire ranging from French chanson to American rock covers. Come another night and you might hear Brazilian melodies or even a bit of classical guitar.

Millers All Day

Brunch all day — three words that when combined together produce a phenomenal idea. It’s the modus operandi of the recently-opened Millers All Day on King and Broad. The interior has the feel of an updated 1950s diner in a grand space. Coffee and cakes are served up front for folks on the go, but if you have time, grab a seat and stay a while.

Following a waitress recommendation, I go with the strata blending grits, roasted vegetables, parmesan, basil. On the side, a plate of homefries dusted with garlic, salt, cayenne pepper, brown sugar, and paprika — “The perfect amount of crispiness and soft inside,” the waitress tells me. I could be misremembering, but I swear I blinked and my plate was clear.

No room for dessert? You’ll get a friendly twist of the arm before you agree to a brown butter coconut pie. Never has “say uncle” tasted so good.

The Darling Oyster Bar

Hankering for some more seafood, I can’t help myself but indulge at The Darling Oyster Bar, starting with oysters. You’ve got options off the Raw Bar from as nearby as Seabrook Island and Bull’s Bay to all the way out from Prince Edward Island, Canada, each offering something a bit different for your palate.

For a main, I’m drawn to the squid ink tagliatelle with Prince Edward Island mussels, ricotta, and creamy tomato sauce. Anything with pasta has the tendency to disappear from my plate in the blink of an eye, but I manage to slow down and enjoy the rush of flavor. Next time, I’ve got my eye on the charred octopus salad.

Jestine's Kitchen

“Are you going to be joining us?” a host asks, catching me as I have a look at the menu.  There’s a familial tone to his voice that sticks out over the more typical, “How many?” that customers are asked stepping into a restaurant.

Jestine’s Kitchen is a veritable Charleston staple on Meeting Street. Restaurants have come and gone (though mostly coming at this point), but Jestine’s has been around since long before Charleston became the culinary celebration it is today.

The name comes from Jestine Matthews, born in the Lowcountry in 1885 to a Native American mother and a father who himself was the son of a freed slave. In her early 40s, she started working for the Ellison family, forging a lifelong friendship. Dana Berlin is the daughter of the Ellisons’ only child and is the owner of Jestine’s Kitchen today, named for the “wonderful style of home cooking and the warm atmosphere that Jestine provided for generations of friends and family.”

I tell myself I’m in the mood for something healthy, but can’t quite take my eye off the pecan-fried boneless chicken breast with fries. Then I see on the menu, “Jestine died at the age of 112…” Well, if it’s good enough for Jestine, it’s damn sure good enough for you.

Bars in Charleston, SC

Before heading to bed, check out The Watch Rooftop Kitchen and Spirts, attached to The Restoration. You can camp out on the rooftop or stay huddled indoors at the bar to enjoy diverse libations ranging from cocktails, beer, and wine to a selection of spirits that will plenty satisfy bourbon and scotch drinkers. Try their take on a Lowcountry classic, the Spoleto signature cocktail. You’ve got Virgil Kaine Ginger Bourbon mixed with Fernet Branca and lemon shrub served over crushed ice topped with a burnt lemon peel. Drink up and know what a craft cocktail really is.

Victor Social Club

Many things can be said about Ernest Hemmingway, but rather than talk about the notorious author, they’d rather drink to him at Victor Social Club. The casual nightspot is a homage to the author, who certainly enjoyed imbibing, with oil paintings referencing his life and work.

Cocktails, too, make special mention of some of Hemmingway’s literary works. Men Without Women, a collection of short stories, is also Victor Social Club’s take on an Old Fashioned using Jim Beam Rye, ginger-black pepper syrup, bitters, and a lemon peel. Feeling experimental? Hemingway Heat takes jalapeno-infused tequila, blending it with St. Germain and strawberry. (Yes, you will feel the heat.)

Head down the alley off Hutson Street — the brick building is covered in ivy — and grab a seat during happy hour (Monday through Friday between 4:30 and 7 p.m.). Consider this the start to your night out in Charleston.

Moe's Crosstown Tavern

Moe’s Crosstown Tavern sits on Rutledge Avenue a block away from Hampton Park. The neighborhood here in Wagener Terrace is a couple of miles north of downtown Charleston and frankly feels a bit like another city with its mid-20th-century housing stock, drive-through food joints, and suburban-style parking lots in front of the Food Lion grocery store and the beige CVS that seems to always come with it. (Still have the palmetto trees, though.)

But with the drastic shift in character comes a different kind of crowd. You won’t find the folks trotting off the cruise ships up here. Instead, you’ll find locals kicking back a Revelry IPA in Moe’s Crosstown Tavern, a sparingly lit sports bar that’s not quite sticky enough to classify as a hole-in-the-wall. Moe’s is one of those bars that looks like it was built into the first floor of a single-family home on a sidewalk with weeds sticking out of the cracks, surrounded by residential buildings. Across the street is a red, white, and blue “Charleston Strong” mural, memorializing the church shooting, on the third base wall of the neighborhood baseball field.

Want to feel like a Charleston local? Ride a bike up here (or take the 20 bus) and have a drink with the working crowd.


There’s a modern, mid-century atmosphere to The Dewberry, just on the edge of historic Charleston and Marion Square. The Dewberry is yet another luxury Charleston hotel, but I’m here for the cocktails in the aptly-named Living Room. Bartenders are dressed in a suit and tie, mixing up drinks on a gold-colored bar and lighting to match.

Struggling to go outside of my box, I order an Old-Fashioned. (Hey, the liver wants what the liver wants.) The Dewberry’s take doesn’t disappoint with perhaps a more potent kick of bitters. And just in case you forgot where you’re drinking, a stylized letter D is forged into the cube of ice.

Charleston Outdoors

Like Paris or New York City, this is a city meant to be explored by foot. Not only has the city taken care to preserve its historic housing stock, giving you plenty to ogle during afternoon jaunts, but Charleston has done an admirable job in incorporating public green spaces within the city where you can find some shade from the punishing summer sun or relax on a bench looking out over the Atlantic.

Rainbow Road

Rainbow Row on East Bay Street is a collection of brightly-colored green, light blue, yellow, and pink 19th-century homes stacked together neatly as if curated specifically for your Instagram account. In reality, it took the likes of preservationist Susan Pringle Frost to turn the collection from a rundown, post-Civil War slum to the tapestry of pastel pink and robust roses admired by camera-clicking tourists today.

Waterfront Park

Waterfront Park opens the Atlantic harbor to pedestrians and cyclists alike. Crushed gravel walking paths trace manicured green spaces lined with palmetto trees. The Pineapple Fountain (labeled cleverly on your Google Maps as ‘Famous Pineapple Fountain’) is the scene of the many-a-posed photograph before couples or families continue over to the railing to watch the sailboats come and go. Grab a seat on a wooden park bench, breathe in that fresh saltwater air, and stay a while.

White Point Garden

On the southern tip of the peninsula sits White Point Garden. The grassy space is lined with sprawling trees crisscrossed with short, more crushed gravel walking paths to the various monuments located in the park, including a variety of Civil War cannons. Controversially, a number of monuments celebrating the failed and pro-slavery Confederacy still stand despite a tide following the racially-motivated killings in 2015 moving in the direction of shunning Confederate symbols to the hallways of museums.

Hampton Park

This is arguably the nicest green space in all of Charleston with nary a tourist in sight. Come here in the early evening hours (perhaps just before a Moe’s Crosstown happy hour) and people-watch the joggers and couples meandering around the gardens. March down the wooded paths with fresh flowers by your side and revel in this lesser-traveled corner of Charleston.

Charleston Art

“The story of American art in this region starts in the 16th century,” says Angela Mack, Executive Director and Chief Curator at the Gibbes Museum of Art. “People came from all over the colonies and Europe because they knew it was a wealthy city, so they could make money on portraits.” That fledgling artistic legacy quickly formed a foundation and by the Civil War, Charleston was a full-fledged artistic hub. “The two armies were the biggest patrons of the arts,” says Mack, noting that both sides commissioned artists to commemorate battles.

Become The Artist

The Restoration offers an Artist In Residency Program that promises artists an “immersive, 16 month opportunity to share their work and have it incorporated in the very DNA of the hotel.” Artists work with the hotel on works that will be integrated into guest rooms, corridors, hallways — even key cards.

Inaugural Artist In Residence, photographer Gately Williams, covers travel, adventure, and exploration in his work, touching on the romanticism and independent spirit that’s felt throughout the United States. Guests can find his limited edition prints throughout the hotel with a select series of custom photos available for sale

Gibbes Museum of Art

Welcome to one of the oldest art museums in the country — the Gibbes Museum of Art. “It was a huge to-do in the art world,” says Executive Director and Chief Curator Angela Mack, referring to the museum’s opening in 1905. “The idea was to create a space in the city, thinking of the city’s state during Reconstruction, to teach young people the ability to have a creative life.”

Besides a museum, the building is once again a working space for artists following a 30-month renovation process two years ago. “We took the building back to its original use,” says Mack, allowing artists to work and teach classes from pre-kindergarten through 12th-grade as well as adults.

As of this writing, there are a number of ongoing exhibits at Gibbes that tell the story of Charleston and the American South. There are the works of the self-taught local artist, Alice Ravenel Huger Smith, a lifelong resident of Charleston and credited as a catalyst of the Charleston Renaissance in the early 20th Century.

Her watercolors and sketches focus on Charleston, but between 1917 and 1919, she became enamored with Japanese-style prints, producing her own work, which can be viewed in the permanent collection. Hale Woodruff’s lithographs depicting the African-American experience and living conditions in the segregated South are likewise not to be missed.