• Charleston is the oldest city in South Carolina and nicknamed the ‘Holy City’ because of its skyline full of church steeples
  • For over 300 years, African-American (Gullah) artisans have been weaving sweetgrass baskets
  • George Gershwin composed his well-known opera Porgy and Bess while living on Folly Beach
  • Lowcountry cuisine – sample dishes like Hoppin’ John (black eyed peas & rice) and She-crab Soup (crab bisque)
  • Traditional Charleston homes have piazzas (or porches) that face south or west to ensure there is lots of breeze
"When he saw General Sherman’s “Yanks” and “Charleston is taken!” - Shovels & Rope


  1. A Southern Mansion tour
  2. Gallery visits
  3. Shrimp & hominy (grits)
  4. Historic carriage tour
  5. Sullivan’s Island day trip
  6. Boone Hall Plantation & Gardens
  7. Porch sippin’ at Zero George
  8. Antiques on King Street
  9. Callie’s Hot Little Biscuit
  10. Oysters and champagne at Leon’s



Charleston chic
Historic luxury
Local charm



  • Palmetto Carriage Tour | Ordinarily, a carriage tour is too gimmick-y or touristy for our taste, but Charleston is the place to do it. The drivers are not merely ‘tour guides’, but licensed city historians. Testing is rigorous and candidates are required to take written and oral exams over the history, architecture and botany of Charleston. Get yourself oriented and learn a lot during the one hour narrated tour.
  • King Street | The renowned street is broken up into different shopping districts. Upper King for design and dining, middle King for fashion, and Lower King for antiques. Don’t miss John Pope Antiques, Alexandra French Antiques and George C. Birlant & Co., one of the largest and oldest antiques establishments in the southeast. Find designer goods from around the world in the beautiful space at WorthwhileHampden has a wonderful collection of women’s apparel and Billy Reid is the definition of Southern style.
  • Xiao Bao Biscuit | It might seem odd to be recommended a Thai food restaurant as your first meal in the South, but you won’t regret a meal here. Try the Okonomiyaki with all the add-ons including ‘pork candy’ and the Som Tum Chicken if you like spicy. Cocktails are creative and also delicious.
  • The George Gallery | A contemporary gallery in a historical house off of King Street with mostly Southern artists.
  • Redux Contemporary Art Center | A nonprofit organization supporting contemporary artists and their work. Be sure to peek your head into the working studios of Lulie Wallace and Teil Duncan.
  • Leon’s Oyster Shop | This place is a photographer’s dream. The attention to detail in decor is unexpected for a place with such a casual vibe. Grab a dozen oysters and sip on a local Holy City brew for an afternoon snack.
  • Holy City Barber | Next door take a peek inside the neighborhood barber shop. Grab a quick shave and enjoy this beautifully curated little space.
  • The Ordinary | Housed in an old bank, this oyster bar/restaurant specializes in seafood caught by local fishermen & crabbers. It’s a stunning space with beautiful dishes. Don’t miss the razor clams if they’re in season and take note of the daily special.
  • The Rarebit | Grab a Moscow Mule at the bar (the copper cup can be yours for $20) and enjoy the mid-century Hollywood decor.




  • Breakfast | For coffee fanatics, Black Tap Coffee is a must. The minimalist chic space is the perfect place to enjoy an iced coffee and croissant. For a larger meal, stop by the The Park Cafe across the street from Hampton Park for a fried egg sandwich and ‘Cold Brew Creation’. Enjoy a leisurely breakfast amongst locals reading the paper or sipping coffee on the patio.
  • Magnolia Cemetery | Wander through the historic site which was once a rice plantation and the final resting place for 6 Civil War generals.
  • Celadon Home | En route to the plantation, this home goods store in Mt. Pleasant is worth a stop. It’s eclectic and European-inspired with timeless pieces. Their Southern hospitality is evident in the relaxed ‘bring your pet to shop’ policy.
  • Boone Hall Plantation | Founded in 1681, a tour of the property gives great insight into life on a working plantation. The oak-lined driveway makes for a spectacular entrance. Be sure to take a look inside the row of cabins where slaves once lived.
  • Sullivan’s Island | Head to the laid-back beachy area just outside of Chucktown. Drive through the neighborhoods to check out the amazing beachfront properties. Swing by the popular Poe’s Tavern for a drink on the sunny porch. The Edgar Allen-themed joint is also known for its burgers. Just down the street, The Obstinate Daughter is a great option for a Lowcountry shrimp roll & fries.
  • College of Charleston | Founded in 1770, the beautiful campus is just steps away from King Street.
  • Zero George | If you’re not spending the weekend at the George, be sure to stop by for a drink on the patio. The expansive porch is perfect for sipping tea and quintessential Charleston.
  • Dinner | The charming little Chez Nous is romantic and cozy. Tucked away in a restored old house on a quiet neighborhood street, you’ll feel like like you’ve been transported to a bistro in France. Another option is the much-hyped brew pub, Edmund’s Oast. Their seasonal menu could hardly be described as ‘bar food’ with dishes like the ‘Carolina Gold Rice Heritage Chicken Porridge’. Not only do they have an impressive 48 unique beers on tap, but the cocktails are excellent as well.
  • Jeni’s Splendid Ice Cream | This is not your average ice cream shop. Jeni’s is made from ‘grass-grazed milk’ with unique flavors like sweet potato with torched marshmallows and sweet cream biscuits and peach jam. Scoopers will give you a taste of their favorites and good luck choosing just one!


  • Breakfast | A trip to Charleston is not complete without a visit to the Hominy Grill. The Shrimp & Grits are solid and the Nasty Biscuit is southern fried goodness. For a quick grab-and-go, do not miss Callie’s Hot Little Biscuits. Choose from a classic buttermilk, blackberry-filled or black pepper bacon. Top it with some cinnamon whipped butter and you’ll be dreaming of these biscuits for weeks on end. Just down the street, Brown’s Court Bakery offers Sriracha croissants (!) and muffins if you’re more of a pastry fan.
  • Indigo & Cotton | Stop by this carefully curated menswear shop to browse brands like Gitman Bros. and Shinola.
  • Aiken-Rhett House | This home built in 1820 remained in the family for 142 years before it was sold to the Charleston Museum. The house has a colorful history and beautiful interiors.
  • Dock Street Theatre | This cultural city was the first to have a theatre built in 1736. It’s said to be one of the most haunted places in Charleston and still hosts concerts and live performances today.
  • Old Slave Mart Museum | Located on one of Charleston’s few remaining cobblestone streets, the building once held slave auctions.
  • Battery Park | This landmark defensive seawall and promenade is also known as White Point Gardens due to its piles of bleached oyster shells. This point was occupied by Fort Broughton and Fort Wilkins during the Revolutionary War and the War of 1812. Fort Sumter is visible from the Cooper River and the area features some of the most beautiful antebellum mansions in the city.
  • Bar Hop | Head toward the cheekily named ‘SNOB’ (slightly north of Broad) for a pre-dinner cocktail. At the Gin Joint, sample a Monticello Mule or a Prize Fighter if whiskey is more your thing. Don’t miss the “Cornbread & Milk” which is exactly what it sounds like. Just a block down the road, saddle up to the bar at McCrady’s, one of Chef Sean Brock’s institutions.
  • James Beard Award-Winning Dinner | Charleston is known for it’s culinary scene, so hopefully you’ll have time to sample it all. FIG  is a local’s favorite where Chef Mike Lata serves gourmet Lowcountry fare. ‘Make Your Own Manhattan’ with dishes featuring local seafood like the fish stew in cocotte and slow baked grouper. At Husk, southern tradition meets contemporary in food and decor. Don’t miss the pig ear lettuce wraps, cornbread and the cornmeal-dusted catfish. If you can’t make it for dinner, grab drinks and appetizers at the stone building bar next door.



Includes every location mentioned above
Lauren Greenberg
Itinerary By

Founder of The Weekender

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