15 Spots You Must Sip, Dine and Stay in Charleston

No matter the season, we’re always fallin’ for Charleston.

I’ve gotta new crush—his name is Chuck(town). We’ve been out a dozen times before—but this time was different. A week felt like a summer fling I never wanted to end. 

He’s at once laid back and luxe. A vibe in all his hip-meets-historic Lowcountry casual-chic glory. His stately soaring steeple-dotted skyline (~400 churches to be exact) gives regal—while his cobblestone streets snaking through downtown bring whimsy. Never mind the herd of horse-drawn carriages, retail for days, esteemed edifices and architecture, pastel antebellum houses, Charleston Harbor (that at once, well, harbors history and a hip hang)—or the smattering of cafes, bars and restos that never met a hankering they couldn’t fix. Like any good fling, our time together wasn’t enough—but somewhere over the rainbow (row) we’ll meet again. Until then, the highlights.

Chic Boutique Stay

Bring the outside in palatial piazza-style via one of the newest boutique hotels to join the ~100 in Downtown. She’s a total mood. From the verdant lobby abloom with literal live plants and outdoor fans to the massive porch swing (get you a Noah to read to your Allie a la The Notebook) to the rooftop vistas worth a short (or long) respite, The Loutrel is pure poetry. The embodiment of modern Charleston with a nod to its history, it’s precisely where you want to lay your head… or laze in the Veranda Lounge over—what else—botanical-inspired boozy ’tails and Mediterranean bites. Bonus: Its prime position in the heart of Charleston’s Historic District just steps from the famed City Market and King Street beckons you out, while the finely appointed rooms with live botanicals, Matouk linens and—ahem—Dyson hair dryers (!) pull you back into the lap of luxury for refuge in a Southern sanctuary like none other. Hey, it wasn’t named the top Charleston hotel by Travel + Leisure for nothin’. @theloutrelcharleston

Live Like a Local

If Carrie Bradshaw had a Charleston crash pad, this would be it. The Restoration will lull you, woo you and restore you—then send you off into the bosom of the retail district to shop, eat and drink your heart out. (Jimmy Choos not recommended.) With two distinct stay ops to select, the choose-your-own-adventure historic hotel serves up a boutique modern experience via spacious hotel suites; or, homey one- and two-bedroom suites for the live-like-a-local-feel we chose. 

The Restoration Charleston

Positioned off King Street, history and hip collide in the latter, serving up rustic-chic spacious well-appointed flats with mod tech and exposed brick—and, well, that “I live here” nonpareil feel. Rise and shine daily to a doorside basket of gourmet goodies (from fruit and yogurt to freshly made breakfast croissant sammies). While there—or just passing by—make it a point to pop down to The Rise coffee bar (pro tip: in season, best lavender latte in town), or, later, level up to The Watch rooftop (ask for Lucas) to join sundry locals and guests alike for lunch, tipples, dinner, views or all of the above (yes, please). And just like that… from coffee to cocktail to slumber, you’re restored. @therestorationhotel; facebook.com/therisecoffeebar; @thewatchrooftop

Culture Vultures on High

It’s a colorful life at The Vendue. If you haven’t heard of this hot spot for its exhibits, artful accommodations or even dining selects, you’ve likely heard of it for its views—and if you haven’t, well, thank us when you’re feeling on top of the world. Elevate your stay by posting up for some sips on The Rooftop with perspective or book a night here—especially for the aesthetes. Either way, add this mod hôtel des arts with historic bones and primo location to your Charleston bucket list. 

The iconic space merges two historic buildings with two distinct well-appointed experiences—each with their own vibe. The common spaces adorned in ~200 art pieces (“a good excuse to show off”) deliver an intentional experience—while on the layered rooftop regal decor turns to welcome reverie… and all are welcome. “Art hotel, not hotel art,” the MO alone reveals what Vendue serves in spades: contagious energy, undeniable flair and inspiration for days (the red-hued ground-floor-level grand piano room has the elevated mystique of House of Cards so much so that I expected Robin Wright to saunter into the room). Color me impressed—though still hopeful for that Wright run-in. @thevendue; @venduerooftop 

Aw, Shucks 

167 Raw, The Darling or Leon’s. Shuck amongst yourselves—we’ll wait. While there may never be an answer to the great Chucktown oyster debate… oh, darling, you can be sure you’ll feast like kings on King Street. They’re all pearls—and, honestly, it just comes down to a vibe check. If you’re the reservation type seeking that classic feel straight out of Southern Charm—aka oozing Charleston from door to food to decor to floor—lean The Darling (and, pro tip: besides oysters (obv), lobster roll. Period). If you have time to spare (and I cannot emphasize this enough—make some), 167 Raw will wow you from the ’tails to the bivalves to the bevvy of fresh selects (those shrimp tacos are borderline criminal). First-come first-serve it like a pro by rounding the corner to Bar 167 to take sanctuary indoors or take to the terrace under the apropos mod “Drugs” decor to fuel your fortitude with Mediterranean-inspired drinks and dishes. 

And locals will tell you that there’s just no slurping oysters in CHS if you haven’t rolled up for bivalves at 2020 James Beard semifinalist Leon’s. A diamond in the rough (er, sea of pearls), Leon’s come-as-you-are garage-chic poultry and oyster shop is a veritable haven of cheap beer (even Miller High Life ponies), “kickass salads,” on-tap rosé and frozen G&Ts, plus ’tails for days—all married in an old garage that accepts walk-ins or reservations for crews rolling six deep or more. @167_raw; @bar167_charleston; @darling_oyster_bar; @leonsoystershop

Carriage ride Charleston

The carriage ride may sound corny, but it’s worth a slow hoof through the Holy City while taking in fun facts like the fact that the “haint” Carolina blue paint on the piazza ceilings is meant to spook the ghosts. Or, wait for it, per my brainy host (find her on Jeopardy soon), pre-AC when fully clothed regal locals needed air in the sultry summer (pun intended) they sat naked on their private piazza—but since those porches are still open on one side, should a nude woman be spotted, her onlooker was forced to propose.

So Nice, Had to Do It Twice

When it’s that good, you go back again. And it’s always Millers time in Charleston. We first told you about Millers All Day last year—but all day means every day for liquid “prescriptions” (the apt sign-emblazoned bar is just what the doctor ordered) or coffee bar sips… and, well,  just to feed the soul with whatever soothes you, all-day breakfast, brunch, lunch or pies by the slice. 

The same rings true for Rancho Lewis—go ravenous and thank us later. (Fun fact: The off-the-beaten-path locale at Pacific Box & Crate is worth its own several-hour brewery, play yard, glutinous adventure). Austin and Charleston collide in this brainchild of Texas-bred top toque John Lewis of Lewis Barbecue fame (like people stand in long lines for this—even on weekdays), honoring the multicultural trifecta of West Texas; New Mexico; and Chihuahua, Mexico, via “border food-meets-cowboy cuisine” that promises to ruin the rest of your Mexican resto dinners in the best way—which is precisely why we returned. Bless this Mex. @millersallday; @rancholewis

Rancho Lewis

Let’s Get This Bread

Scratchmade biscuits and bennies 🤝 mimosa flights and full bar—say less. At Ruby Sunshine, “brunch is a lifestyle.” Read: They live for it—and you will too once you bite into #thatbrunchlife. Hey, if the ruby slipper fits, we’ll eat it. (Pro tip: The Downtown East Bay Street digs are perfectly positioned to fuel you for your short jaunt to the waterfront, Rainbow Row and more.) 

If you’re in more of an “empire state of mind” you’re gonna wanna “Be” the “Yoncé” you wish to see in the world and nab that Jay-Z energy at NYC-inspired open-all-day Bodega. One promise: a droolworthy (and ’Gram-worthy) cheese pull. Situated in an 8K-square-foot train depot alongside Share House—and serving up colossal cheekily dubbed breakfast sandwiches—the graffiti-laden locale transports “concrete jungle where dreams are made of” into the Holy City a la executive chef Alec Gropman’s childhood. Go for the vibes alone, fuel up on the bites and bevs (think morning-pick-me-up cuppas from its coffee bar), and stay for the best espresso martini we found in town (no, seriously)—or any of its craft cocktails really. TBH, Bodega is so good we literally ate there twice. @rubysunshinebrunch; @eatdrinkbodega

Color Us Obsessed

If you want to grab ole Chuck by the horns, post up on Meeting Street at recently bowed Matador, from owner NC native Zak Melang. Go for the transcendent tacos and scratchmade super-fresh seasonal authentic Mexican bites—stay for the Gen X/millennial bangers and rustic hacienda-inspired style. We see your vibrant stained-glass window and Old-World Mexican-style antiques and groovy reclaimed wood bar and raise you a custom-built metal fireplace—NTM a spacious patio. Then take flight (literally, order flights) with agave sips from one of the largest tequila programs in the Carolinas. Open daily, the newest hot spot also serves another lunch op to hungry revelers, business-trippers (word) and locals alike. Oh, and late-night happy hour is a thing. @thematadorsouth

Matador Charleston

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About the Author

Angela Brown
Angela Brown is the author of our Business & Economy section.