The Ultimate Weekend in Charleston, South Carolina

Charleston is the epitome of Southern charm. Quaint streets lined with sprawling, pastel homes and palm trees. Some of the nicest people I’ve ever met. And, seriously good eats.

After spending a long weekend in downtown Charleston, I realized nothing is truer than this statement: north is a direction, south is a lifestyle.


Interesting Attractions

  • Explore Charleston on foot: A walking tour hadn’t been on our list of things to do until we found a great Groupon deal ($10 for a 2 hour tour of Historic Charleston). I’m so glad we decided to do this! Strolling through the streets of Charleston and listening to Paulette share interesting facts was a fun way to get a real feel for the city and its history. As you’re wandering, you’ll see a lot of carriage tours, but I prefer the walking version because it feels more personal and you’re able to take photos as you wish. Paulette also offers a ghost tour at night for those who want to learn about Charleston’s spooky side
  • See Historic Charleston: Parts of Charleston feel suspended in time, thanks to its antebellum architecture. The window boxes Charleston is known for were one of my favorite things to check out as we wandered around town. Also, the secret gardens tucked away in alleyways are absolutely adorable
    • A fun fact I learned on our walking tour- a lot of the homes in Charleston use a layout called the Charleston single house. Well-suited to long, narrow lots, which were laid out in early Charleston, a single house has a narrow side with a gable end along the street and a longer side running perpendicular to the street


  • Head to the Waterfront Park: Home to the Pineapple Fountain, this park is perfect for a picnic or relaxing in shade on a sunny afternoon
    • Wondering about the Pineapple Fountain? Back in the day, before returning to Charleston, a sea captain’s last stop would likely be somewhere tropical. As part of their loot, they’d bring home a slew of tropical fruits. Upon arriving home after a long voyage, the captain would spear a pineapple on his fence post to let friends know he had returned safely. Seen as a symbol of hospitality, the pineapple became an invitation to come over for drinks and stories of adventure


  • Check out Rainbow Row: A Charleston staple, there are a few rumors about how the series of thirteen Caribbean colored homes got their name. Historians believe homes on Rainbow Row were painted their pastel hues when one woman bought and renovated several of them to save from demolition. In actuality, that’s probably what happened, but I prefer the local myth, which claims the houses were painted in various colors so intoxicated sailors coming in from port could remember which houses they were staying in
    • After you check out the pastel-hued homes, continue heading south to the Battery & White Point Gardens. It’s a public park at the tip of the peninsula, shaded by stately oak trees and surrounded by breathtaking mansions


  • Stroll through Old City Market: Boasting 300 local vendors, this open-air market stretches four city blocks and is one of the oldest city markets in America. Vendors change daily and sell everything from sweetgrass baskets to handmade jewelry and candied pralines


  • Go Shopping on King Street: The best stretch of shopping is from Marion Square to Lower King Street, a few of my favorites:
    • Candlefish: Gorgeous shop selling its own brand of candles and carefully curated selection of small gifts. We weren’t able to try one of their famed candle making classes, but we did spend time at the candle library- blindly sniffing scents until we found ones we loved. Such a fun and charming shop to visit, and all of their hand-poured candles are soy-based
    • Savannah Bee Company: Come here to taste different varieties of honey, including whipped honey
    • Impeccable Pig: Cute clothing boutique
    • Also, Mac & Murphy is a cute local stationery shop not located on King Street, but it’s a short walk (reco checking it out if you visit Hominy Grill to eat)


  • Visit a plantation: Plantations are part of Charleston’s history. On our trip, we took the Greyline to Boone Hall, which is still a working farm. The plantation itself has a lot of history- on our visit, we toured the house, watched a Gullah presentation, strolled down the Avenue of the Oaks and took time to take in the well-preserved slave cabins


  • Old Slave Mart Museum: ~40% of all enslaved Africans coming into the United States in the 18th century came in through the Port of Charleston. This museum is the only known former slave auction gallery still in existence


  • Hampton Park: If you’re staying nearby, as we were in an Airbnb, this park is a great place to go for a morning walk or run- beautiful and well-kept gardens


Where to Get Coffee:

  • Black Tap Coffee: Loved this place so much, we came back twice. Cold brew is great, but the coffee cocktails were my favorite thing on the menu. Recommend trying the Black Julep- espresso, cold brew, mint and honey
  • Kudu Coffee: Liked the vibe of this place a lot, plenty of indoor and outdoor garden seating
  • Tricera Coffee: Coffee & dinosaurs? Two of my favorite things! Tricera’s close-location to King Street makes it a good place to stop if you need a mid-afternoon pick-me-up from shopping/wandering


Where to Eat:

  • HUSK: Unable to get a dinner reservation here, we came for lunch on our first day in Charleston. Everything we tried was delicious. Using only ingredients from the south, HUSK nails hearty home cooking
  • Hominy Grill: Located in a historic Charleston single house, Hominy Grill feels as though it has been open for generations. It’s southern food perfection, you have to try the shrimp and cheese grits
  • Callie’s Hot Little Biscuit: Is there anything better than bacon, egg and pimento cheese on a fresh baked biscuit for breakfast?
  • Glazed Gourmet: Come here early for delicious doughnuts with quirky flavors- we loved the apple bacon fritter and lemon old fashioned
  • Butcher & Bee: Located on Upper King Street, this sandwich shop is right by The Daily. The menu changes daily, but we tried a grilled cheese with zucchini ribbons and brunch biscuit sandwich. Be sure to stop by The Daily before you leave for homemade cold-pressed juice or cold brew
  • Jeni’s Splendid: This place has been on my to-try list forever, but somehow, I never make it to one of their locations when I’m in LA or Chicago. Went a little crazy here and ordered a double scoop with brambleberry crisp and salted caramel ice creams, topped with salted caramel sauce and bitter chocolate fudge. Simply amazing, crossing my fingers Jeni’s opens a NYC outpost soon
  • Poogan’s Porch: Southern classics done right. The pimento cheese fritters were delicious. While we enjoyed having dinner outside on the front porch, if I had to choose between here and HUSK, I’d dine at the latter
  • Coast Bar & Grill: We came here one night after a few cocktails and were pleased to find a chill environment to enjoy a few appetizers (fried green tomatoes!). The full dinner menu looked good, so I’d consider this a solid option if you’re on King Street and need somewhere to grab a bite
  • Mercantile & Mash: Charleston’s first fancy food court, it’s a good place to grab lunch if you’re nearby
  • Kaminsky’s: You can’t come to the south and leave without having pie. Bonus: Kaminsky’s also has a full bar. Order the Tollhouse Cookie Pie & Brandy Alexander
  • Sugar Bakeshop: The cupcakes are delicious, but the courtyard was our favorite part of this little bakery


Where to Drink:

  • The Gin Joint: One of my favorite cocktail bars in Charleston, this place revamps their menu seasonally. We came a week after they introduced the spring menu and weren’t disappointed. If you’re there when the Studmuffin (Charleston Madeira, Hoodoo Chicory Liqueur, St. George Coffee Liqueur, Amaro Sibilla, Sumac Bay Leaf Ice Cubes) is on the menu, I highly recommend ordering it
  • Proof: Another one of my favorite bars in Charleston. They have a great happy hour, but also a solid cocktail menu. Grab a seat at the bar and work your way through their drink list- my favorite one: the Martinez, served with a cheese slice garnish
  • The Belmont: Cozy bar with old black and white movies playing on the side wall
  • The Cocktail Club: Great cocktail menu, nice bar area and plenty of seating. We visited on a warm spring night and enjoyed sipping drinks on the rooftop
  • The bar at HUSK: Outstanding selection of bourbon and whiskey. I’m a big Madeira fan and appreciated the ones they have on the menu here
  • The Griffin: A dive located near HUSK, it’s been a local staple for 20+ years
  • Bay Street Biergarten: Perfect place for a few beers in the afternoon sun
  • Amen: Come for the afternoon happy hour (4-7 pm at the bar weekdays). Great drink specials and half-price fresh oysters
  • McCrady’s: I’ve heard good things about the tasting menu here, but we came for cocktails. If you’re a Madeira fan, this is a good place to try a few varieties


A few other recommended restaurants/cafes we didn’t have a chance to check out:

  • Taco Boy: Margaritas + tacos
  • FIG: I’ve heard this place is as good as HUSK, will def check it out on a return trip
  • Wildflour Pastry: Doughnut muffins!
  • Caviar & Bananas: Said to be similar to Dean & Deluca, come for brunch
  • Indaco: Recommended for brunch and burrata
  • Two Boroughs Larder: Hipster southern grocery store with great noodle bowels
  • Edmonds Oast: Local favorite with a top notch beer selection

We spent most of our time in downtown Charleston, but if you want to see more of the surrounding area, I’d suggest renting a car and checking out Isle of Palms, Sullivans Island, or Folly Beach- all barrier islands off the coast.

Because we stayed close to Harleston Village, we opted not to rent a car- walking everywhere was really easy, our longest walk was ~15 minutes. On late nights out, we took Uber home. At the time of our visit, Uber rates had just been lowered, and most rides cost us $2-6 (super cheap!). To put it into context, we took an Uber from Harleston Village to the airport outside of downtown for $14- taxi rides covering the same distance are over double that.

Have you ever been to Charleston? What was your must-visit attraction or place to eat?

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A First-timer’s Guide to Charleston, South Carolina: Where to Visit, Eat, Shop, and Sleep

A First-Timer's Guide to Charleston, South Carolina |

After my First-Timer’s Guide to Savannah, Georgia, made some waves, I figured that the time was right for me to impart my knowledge about my beloved hometown of Charleston, South Carolina. I was born here, and other than an eight-year-gap when I lived elsewhere in South Carolina, I’ve called Charleston my home my entire life.

From school field trips to my own wanderings, I’ve seen most of what the Holy City has to offer. If you’re heading this way on a trip, here are a few ways to make the most of your stay.

Where to Stay

If you’re staying in downtown Charleston (aka the Peninsula), there are plenty of options for every budget.

  • The Holiday Inn Charleston Historic District is one of the newest hotels on the peninsula. It’s just a block from the Visitors Center and within easy walking distance of Marion Square and King Street.
  • The Days Inn and the King Charles Inn (both on Market Street) are two of the lower priced options in the downtown area that are still in safe, walkable areas. Note that both of them have been there for as long as I can remember, so I can’t speak to how well they’ve been updated.
  • On the other end of the spectrum, Charleston has some amazing high-end hotels. Book a stay at the Wentworth Mansion, the Charleston Place, or the Francis Marion Hotel to experience luxurious accommodations in the middle of the historic district.
  • There are also many smaller boutique hotels such as Zero George, 2 Meeting Street Inn, Planters Inn, Fulton Lane Inn, Ansonborough Inn, and Vendue Inn if you’re looking for a more intimate experience.
  • If you’re willing to drive over the Ravenel Bridge to Mount Pleasant or the Ashley River Bridge to West Ashley, you can get some great deals on large chain hotels such as Hampton Inn, Extended Stay America, and Quality Inn.
What to Eat

Charleston has so many great places that I don’t think you can really go wrong no matter your budget, tastes, or style. I’ve broken down some of my favorite restaurants into a few different categories, and then suggested favorite dishes at each (since I’m allergic to shellfish, any recommendations for seafood have come from family and friends). Note that not all of these are in the historic district!

A First-Timer's Guide to Charleston, South Carolina |
Fuel Restaurant


  • The Ordinary (downtown): oysters on the half shell
  • O-ku (downtown): sushi, chicken teriyaki
  • Red’s Ice House (Mt. Pleasant and Seabrook Island): fish and chips
  • Husk (downtown): the menu rotates seasonally since all of the ingredients are locally sourced
  • Fuel (downtown): braised pork tacos, hoe cakes
  • Poe’s (Sullivans Island): blue cheese coldslaw, any of their burgers

Classically Southern 

  • Poogan’s Porch (downtown): fried green tomato BLT, crab cakes, ham macaroni and cheese
  • Jestine’s (downtown): pecan fried chicken, fried okra, sweet tea
  • Sewee Restaurant (Awendaw): fried flounder, potato salad, any dessert
  • Virginia’s on King (downtown): pecan fried chicken, macaroni and cheese


  • Groucho’s (downtown and West Ashley): mushroom cheese melt or the Pink Moose
  • Fire Grill (downtown): chicken teriyaki
  • Tzakiki’s (downtown and Mt. Pleasant): traditional gyro
  • Andolini’s (Mt. Pleasant, West Ashley, North Charleston): standard cheese pizza or calzone


  • Eli’s Table (downtown): filet mignon, pimento cheese and tomato appetizer
  • Peninsula Grill (downtown): the coconut cake


  •  Hominy Grill (downtown): omelet, biscuits
  • Acme Cantina (Isle of Palms): the Southerner (sweet tea fried chicken on a biscuit)
  • Charleston Cafe (Mt. Pleasant): waffles, Amber’s Choice (egg-topped crab cake)
What to See

Charleston has some tried and true attractions–I’m a firm believer that some things are popular because they’re good. So, while you’re here, try out a few of the big attractions, but don’t forget to mix in a few hidden favorites as well!

A First-Timer's Guide to Charleston, South Carolina |
Hampton Plantation, McClellanville

Plantations are a part of Charleston’s history, so if you’d like to learn more, you need to head out to see the Ashley River Road plantation district. The big three areMiddleton Plantation, Drayton Hall, and Magnolia Plantation. Of the three, Magnolia is my favorite since there’s a great petting zoo, extensive gardens, a butterfly house, and restored slave quarters in addition to a tour of the main house. If you’re willing to drive further away from downtown, Hampton Plantation in McClellanvilleis never crowded and, with its wide front porch and classical architecture, looks more like a stereotypical antebellum plantation.

Many of the rich planters also had fashionable “city” homes in downtown Charleston, so you can get the full story by visiting both the plantations and the houses in the historic district. The Edmonston-Alston House, the Nathaniel Russell House, and the Aiken-Rhett House are all within easy walking distance of the rest of the historic district.

A First-Timer's Guide to Charleston, South Carolina |
My husband and our dog on Isle of Palms

If you’d like to see more of the Charleston area, I highly recommend renting a car or taking a cab out to one of the beaches. Isle of Palms, Sullivans Island, and Folly Beach are all barrier islands just off the coast of Charleston, and each has its individual charms.

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