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72 Hours in Charleston

How to make the most out of the Holy City, Charleston, South Carolina.


Charleston residents have a favorite story to tell. After the Civil War, as General Sherman traveled through the South burning and destroying its cities, he had mercy on Charleston. He was so taken by Charleston’s beauty (or that of a Charleston woman, depending on who you ask) that he spared it, refusing to destroy it in the way he had destroyed other cities.

Many of the same historic homes, parks and cobblestone streets that charmed Sherman in 1864 still remain today, and the story of Charleston’s resilience gives its residents a palpable sense of pride. But a fast-growing population of young people (from 80 to 100 new residents arrive daily, depending on who you ask) is slowly changing Charleston from its historical and traditional roots. Liquor stores still close on Sunday, but young people flood downtown every week for Sunday day drinking. Civil War-era, historic homes now find their antithesis in new apartment communities. Horse-drawn carriages share the road with cyclists and surfboard-toting Jeep drivers.

What seems to remain unchanged in Charleston, though, is its charm — carried both visually and through the merits of Southern hospitality. Charleston lacks nothing in the way of great restaurants, bars, places to stay, activities to enjoy and conversations to have. Whatever your interest, here’s how to make the most of a weekend in this Southern city full of contrast.

Introduction and additional reporting by Caitlyn Girardi.

Where to Stay

A Brand-New Boutique with a View, or an Old Standby

Photo: The Dewberry

The hotel scene in Charleston has, until recently, failed to keep up with the city’s surge in tourism. But The Dewberry, opening in mid-June with 155 rooms on the east side of Marion Square in downtown Charleston, will help to fix those vacancy issues; it’ll also be the nicest digs in town, filling the old Mendel L. Rivers Federal Building with “modern Southern” design and transforming the parking lot out back into a verdant garden lined with live oaks and palmettos.

The other luxe-traveler favorite is Belmond Charleston Place, rated #1 by Conde Nast Traveler readers in 2014. Amid its stately marble interior is just about anything a spoiled guest could want: an in-house restaurant, a wealth of fancy shops, a saltwater infinity pool under a retractable glass ceiling, and so on.

Francis Marion Hotel | $170+/night | francismarionhotel.com
Iconic, traditional, and located, like the Dewberry, directly on Marion Square.

Restoration on King | $239+/night | restorationonking.com
Apartment-style, exposed-brick rooms give you the city experience not typically associated with the South. Feel like a resident with your own kitchen, but enjoy the spoils of being at a hotel with grocery delivery, in-room wine and snacks, rooftop terrace, bike rentals and nightly wine-and-cheese reception.

NotSo Hostel | $28+/night | notsohostel.com
It might be the town’s best accommodations for young people looking for a place to sleep, grab breakfast and then go. It’s made it to the pages of local papers and the New York Times alike, offers comfortable, safe accommodations, organic coffee and bagels, and a community feel typically associated with European travel.

Where to Eat

Seafood, Italian, and More Seafood


Charleston is one of America’s greatest foodie destinations — and the competition tastes delicious. Start your day at Kudu, the city’s purveyor of locally roasted coffee and local craft beer. You won’t be expecting good Italian on this East Coast peninsula, which makes chef Ken Vedrinski’s Tuscan fare at Trattoria Lucca pack an even greater wallop. (Travel & Leisure recently listed it as one of the top 20 Italian Restaurants in the US.) Chef Mike Lata has the best local seafood in Charleston at The Ordinary, located in an old bank downtown; his former protégé, restaurateur Brooks Reitz, just opened Leon’s Fine Poultry and Oysters in up-and-coming North Charleston for a more small-bites feel that works perfectly for lunch.

End the evening by challenging yourself: try to find the Burns Alley bar (without GPS) by locating the secret map hidden under a restroom floor tile at La Hacienda on King Street. The map also doubles as a free beer coupon (this is not a drill).

Hominy Grill | $$ | hominygrill.com
For the quintessential Southern breakfast or brunch (or lunch or dinner, for that matter), have the shrimp and grits.

Pink Bellies | $ | pinkbellies.com
A food truck camped out on George St., good for anything from a sumptuous Banh Mi to a broth bowl.

Husk | $$ | huskrestaurant.com
Talked-about to death — for a reason. In the words of chef Hugh Acheson, “what Travis Grimes is doing with the native foods of the area, under the leadership of Sean Brock, is a true look at the Lowcountry.”

Tip from a Local


“Charleston and Sullivan’s Island have celebrated and claimed Edgar Allan Poe over the years, even given the fact that there’s really nothing to go off of. He was here for a year, but he left really no traces. There’s no marker at Fort Moultrie, but I think a lot of Poe aficionados go there, because there’s still a portion of the fort that was there when Poe was stationed there in 1828. There are a few streets named for him — there’s an Edgar Allan Poe street, a Gold Bug, I think there’s a Raven street. There’s a little island right when you come onto Sullivan’s Island that’s called Gold Bug Island.

“The biggest thing is probably Annabel Lee. It’s very much made up — a true urban legend. At some point in the 1960s, people started talking about the possibility that the poem Annabel Lee was about a woman Poe met when he was stationed here at Fort Moultrie. There is no historical evidence for that whatsoever. He wrote the poem the last year of his life. He hadn’t been in Charleston in twenty years. And if it is directly about anybody it would almost certainly be about his wife who had died a couple years earlier.

“But a woman who’s still alive and still writes letters to the local newspaper wrote a letter to the local newspaper in 1969, sort of jokingly saying, basically, ‘Why don’t we start telling tourists that Annabel Lee is buried in Charleston?’ Because at that time, Charleston wasn’t nearly the tourist destination that it is now. She said, we can really attract some visitors if we promote this legend of her being a Charleston belle. That letter then got reprinted in a sort of souvenir-book edition of The Gold-bug. It’s really just a tourist souvenir. I have a copy of it now. There’s an afterword where they talk about this legend. And from then on it starts to get treated as if it’s really true.

“When I was doing my research, I called the woman who had written the letter, and just asked her about it. She was really fun to talk to. She just said, we basically made that up. And she was very amused by the fact that people are still talking about it years later… Charlestonians have been repeating it ever since.”

– Professor Scott Peeples, over dinner at Poe’s Tavern, Sullivan’s Island

What to Do

Slow Things Down


Any one of the city’s tours — ghost tours, historic home tours, walking tours — are worth the money to get acquainted with the city; even better, rent a bike at The Bicycle Shoppe or Affordabike and take the Battery2Beach path over the Ravenel Bridge to Sullivan’s Island, or “Sully’s,” as locals call it. Lock up your bikes where the pavement meets the boardwalk, and enjoy Charleston’s comparatively less touristy beach; make sure to stop at Shem Creek along the way. Finish the evening with a hot dog and a River Dogs baseball game.

Westbrook Brewery | $$ | westbrookbrewing.com
Charleston’s best beer, with a focus on funky stuff. Don’t miss the Mexican Cake, a chocolate chili stout that tops many lists of the style’s best.

The Mezz | $$ | mezzdowntown.com
Perfect if you’re in the mood for a night of local jazz music, drinks and dessert downtown.

Charleston Municipal Course | $ | charleston.gov/golf
If you’re not heading to Kiawah, it’s a great local links.

What to Pack

The Gear You’ll Want

Standard Adjustable Cap by Ebbets Field Flannels $65

3 Button Blazer by Beams Plus $449

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