A 3-Day Itinerary for Charleston, the South's Most Charming City

WRITTEN BY THE CITRINE COMPASS FOUNDER, KALYN SALINAS

 

There is just something about a southern city that always draws me in. Maybe it’s the romance of the 18th century historic homes, maybe it’s the warm, sweet air, but I think it’s most likely that southern hospitality.

Charleston has quickly become one of my favorite cities in the United States. You can find old world charm, an incredible food scene and a warm welcome from everyone you meet. It’s that combo that make it the perfect place to have a long weekend.

We hadn’t been in Charleston for more than 24 hours before receiving two handwritten notes from locals detailing the best spots to eat and drink. I thought this might have been a fluke - we just happened to forge a deeper connection than most with our waitress and the owner of the antique store we stumbled into.

But then the extensive recommendations kept coming; the patron sitting next to us at the rooftop bar, the owner of our inn, the clerk at the antique shop. Everyone was willing to recommend a hidden gem to have a cocktail or their favorite burger in town, all for the sake of being helpful.

What’s more is that the locals are extremely proud of Charleston; the historic sites, the culinary explosion, the historical preservation and the art. They truly and madly want you to enjoy all that Charleston has to offer.


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UPON ARRIVAL

You will fly into Charleston International Airport and then check in to newly redone Hotel Emeline* centrally located in downtown Charleston near the French Quarter. Keep it easy and dine at Frannie & The Fox, a trendy Italian eatery in the hotel; sit in the twinkling courtyard if weather permits, get a craft cocktail and don’t sleep on the meatballs.

*Hotel Emeline is part of The Citrine Compass’s partner portfolio and we are able to get members of our community VIP perks such as complimentary breakfast for two each morning, hotel credit, early check-in, late check-out and room upgrades, subject to availability. Reach out to us here to access our insider connections!


3-DAY CHARLESTON ITINERARY

DAY ONE

Start the first day with coffee in your room, hand-delivered by Hotel Emeline’s staff, and then a quick spin on the Peloton in their fitness center to prepare for the coming indulgences.

You’ll spend today getting acquainted with the city, seeing the lay of the land and deciding where you might want to spend more time. The Historic Charleston City Market is a flea market style, open air arcade that is walking distance from the hotel and is a great place to start the day. After shopping for some tchotchkes, begin your stroll in the French Quarter, a historic district which is chock-full of art studios, restaurants and boutiques.

Get your caffeine fix at Harken Cafe and delight in whatever baked good they are whipping up fresh that day. We were lucky enough to nab quiche and coffee cake but once something sells out for the day, it’s gone for good.

You’re now fueled up for your walking tour. The "holy city" as Charleston is familiarly called, was founded in 1670 so it’s history is incredibly rich and the stories shared on the guided tour will give nuanced context to the city. There are tons of good ones on Tripadvisor, so pick your poison depending on your interests and strap on those walking shoes.

We chose an offbeat tour offered by Lowcountry Walking Tours called called “Charleston's Alleys and Hidden Passages” that started at the Old Exchange in the historic center of Charleston but quickly veered into the neighborhood’s quiet alleys and cobblestone streets. Our guide took us past The Williams Mansion (formerly called The Calhoun Mansion) which is the largest single-family residence in Charleston and jam-packed with opulent antiques. We then ambled through the serene drives south of Broad Street to hear stories about the meaning behind the beautiful architecture, palm trees and unseen alleyways.

We got a quick history on the Civil War in White Point Garden and strolled on The Battery, a seawall promenade overlooking the Charleston Harbor. Your tour will probably take you past Rainbow Row, a stretch of tightly packed, brightly colored homes on East Bay Street but if it doesn’t, make it a point to walk along one of Charleston’s most photographed streets.

You’ll work up an appetite with all that walking so put your name in at 167 Raw for fresh seafood (and put your name in as early as possible, it’s popular) before spending the afternoon exploring the quaint boutiques and antique shops a short walk away on Queen Street and King Street. Don’t miss the Preservation Society of Charleston for a curated selection of local artisan crafts and books.

After lunch, head over to Waterfront Park to see the famous Pineapple Fountain (pineapples are a sign of hospitality in the American South) and imagine the port city that Charleston once was. Head home along East Bay Street where you can shop for souvenirs, pop into a few art galleries and grab a happy hour craft cocktail at Doar, where the bar seats stay warm and the truffle popcorn stays delicious.

Dine al fresco tonight at La Farfalle, an upscale Italian eatery with a twinkling courtyard that is just a quick jaunt from Hotel Emeline and located in Charleston's downtown area.


DAY TWO

The Emeline has complimentary bike rentals so pedal down to Millers All Day and get on the list for brunch; the wait, amazingly, never seems to drop below an hour and thirty minutes.

Pass the time soaking in the grandiose homes south of Broad, which quickly became some of my favorites streets in the south. You’ll see Bahamian-inspired colors, plantation-style “single houses” built long and narrow so the breeze could reach as much residential real estate as possible in the humid South Carolina summer and antebellum estates complete with water features and manicured gardens. The homes along the waterfront are quite amazing too so take advantage of those bikes and cover some ground.

When you’re ready to rest your feet check out of Hotel Emeline and head uptown to your next accommodation, 86 Cannon Inn, a renovated 1800s home turned into one of Charleston SC’s chicest boutique B&Bs. The hotel entrance is unassuming but you will quickly find the property to be an oasis, complete with two piazzas (the southern term for porch), a private garden and a reading room in the loft.

European style breakfast is served daily with pastries that the taste-making couple that run 86 Cannon collect fresh from Baba’s Restaurant down the street as well as homemade yogurt and granola. Later in the afternoon you will be served an artisanal wine and cheese pairing to tide you over in the afternoon and local chocolates hung with care on your door every night. If the hotel isn't completely booked up be sure to ask Marion, the owner and a former architect, to take you on a quick tour of the inn’s four unique rooms to share details on the inspired design.

If you loved the tours of Charleston's historic buildings and want more staged nostalgia, Aiken-Rhett House Museum and the Joseph Aiken Mansion & Carriage House are both up this way; for more modern home and design delights, check out Fritz Porter boutique.

Dinner tonight is at Tempest, which will be jam-packed, vibrant, and serving up exquisite seafood. I still find myself dreaming about the hot buns and seaweed butter.

If you have room, Carmella’s is a dessert bar around the corner and worth the line that usually wraps around the building. The night owls can find many a venue playing live music, with The Cocktail Club and Vintage Lounge being some of the most popular.


DAY THREE

Today is your day to venture out of the city and explore some of the historic plantations. If you can’t tell, I love antiques, so head across Ashley River to South Seventeen on your way out of town to pick through their old world delights.

There is amazing down home cooking in the south but you’ll be lunching al fresco at James Beard award-winning Rodney Scott BBQ. Get ready for one of the best meals of your trip!


 
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