Okay, full transparency, we were actually in Charleston for four days. But here’s the thing about that city: you could spend four days there and still feel like you only scratched the surface. Or, if you plan it right, you could have one of the most memorable weekends of your life in 36 hours flat.
We were hosted by Explore Charleston and what I came away with – beyond a serious biscuit obsession — was this: Charleston, South Carolina is one of those rare cities where history isn’t just on a plaque. It lives in the food, the architecture, the people, and the stories that pour out of every cobblestone alley.
Below is how I’d spend 36 hours in Charleston if I were heading back. And being just four hours down the road from Raleigh, I very much intend to. If you choose to experience several of the attractions/tours in Charleston (many we mention in this post) you might want to purchase a Charleston Tour Pass – it will save you around 40% on prices.
Friday Lunch: Arrive and Wander Historic Neighborhoods
Check in somewhere beautiful and give yourself a couple of hours to just wander the French Quarter and South of Broad neighborhoods, and the Battery. This is downtown Historic Charleston at its best. We left Raleigh at 7am to arrive by lunch.
Accommodation: French Quarter Inn
We stayed at the French Quarter Inn on Church Street, and it set the tone for everything. Named a top 5 hotel in the U.S. four years running on TripAdvisor, it’s a 50-room boutique that absolutely earns that title — champagne on arrival, locally sourced artisanal breakfast, wine and cheese pairings in the afternoon, milk cookies and port at night, impeccable Southern hospitality, free bike rental, and a pillow menu. A pillow menu. Seven options. I didn’t know I had preferences until I had options. Those pillow menu options come with turn down service and bedside chocolates of an evening! See rooms and availability here.
And the French Quarter Inn’s location was everything. Steps away from the historic City Market, Restaurant Row, boutique shopping on King Street, the Pineapple Fountain at the waterfront, and the hidden alleys and cobblestone streets of one of Charleston’s oldest neighborhoods. P.S. I do feel I need to warn you: The French Quarter Inn has mini-M&M’s available 24 hours at the front desk. My daughter and I had no self-control.
Lunch: Poogan’s Porch
We asked our Facebook community for their Charleston tips before we left, and the most-recommended answer by a mile was Poogan’s Porch. I’m so glad we listened, because Poogan came up on practically every tour we did after that, which tells you everything! Poogan was a little dog whose favorite spot was the porch of what had just become a restaurant in 1976, his family’s former home. He became so beloved by diners (who, let’s be honest, kept slipping him morsels) that he never really left. He’s buried right beside the porch stairs. Legend has it that if you feel a wet brush against your leg during dinner, it’s Poogan’s ghost still hoping for a bite.
The food gives him plenty of reasons to haunt the place. Expect proper Southern — (famous) shrimp and grits, biscuits and gravy, Lowcountry hash. But the star of our table was Savannah’s chicken and waffles with peaches and bourbon huckleberry syrup. Honestly? No wonder the poor pup’s heart gave out.
French Quarter District ➡️ The Battery
The French Quarter only got its official name in 1973, the same year it earned a spot on the National Register of Historic Places — but it’s been a French neighborhood since the 1600s, when Huguenot Protestants settled here. That history is still written into the streetscape if you know where to look. Here’s what I’d suggest for the afternoon. Pick and choose to suit your pace or save some for your free time later in the trip.
Harken Café
If you need a caffeine fix (and you will), the foliage-covered porch at Harken Cafe is exactly the right speed for a leisurely Friday afternoon. Best coffee and ambiance in Charleston, in our opinion. We went twice. We saw lines snaking out the door on a couple of bike rides past throughout our stay. (Pssst. We’re Aussies, we know great coffee!)
Iconic buildings and photos
Stroll past the pink French Huguenot Church, one of the most photographed buildings in the city. Then cross the street and turn back toward St. Philip’s Church steeple — ideally timed with a passing horse and carriage — and you have one genuinely epic Charleston shot. While you’re there, pop your head into the gorgeous Dock Street Theatre for a quick self-guided look at its extraordinary interior. It’s free and takes ten minutes.
The Old Slave Mart Museum
Sobering, important, and not optional if you want to understand Charleston honestly. The Old Slave Mart Museum documents the slave trade and the lives of enslaved African Americans in one of the most significant slave trading regions in the country. The museum is housed in the old Ryan’s Mart, where enslaved people were bought and sold. It’s uncomfortable, as it should be. This, combined with the Gullah experiences we had later in the trip, helped me come home with a fuller understanding of this region I now call home. The South’s story is complicated and layered, the more we lean into that, really listen and really learn, the better neighbors and community members we become.
South of Broad and the Battery
Stroll past the grand piazza houses, those long narrow single-style homes designed to catch the Lowcountry breeze, down to White Point Garden. When we visited, the live oaks gave the birds space to sit and poop on my dress (lol #keepingitreal) and the azaleas were in full bloom. The views take in the Ashley River, the Cooper River, and Fort Sumter — where the first shots of the Civil War were fired — all at once. The Battery promenade and seawall runs along East Battery Street, named after the artillery battery that once stood nearby.
Historic home tours
We tried to squeeze one in and couldn’t quite time it. If you can, these three are worth it:
- Nathaniel Russell House, famous for its soaring free-flying spiral staircase (you can wander the gardens for free and stand slack-jawed in front of the towering magnolia tree)
- Edmonston-Alston House, a Greek Revival and Federal blend with harbor views
- Heyward-Washington House, one of the oldest surviving residences in Charleston and a place where George Washington actually slept.
- NOTE: Entry to these homes are included in the Charleston Tour Pass.
Rainbow Row
On your way back, turn onto East Bay Street for the obligatory photo in front of Rainbow Row, the 13 pastel-painted terrace homes. Yes, it’s on every tourist’s feed. Do it anyway. They really are that pretty. Go early in the morning if you want to beat the crowds!
Pineapple Fountain
End at Waterfront Park, where the Pineapple Fountain is a classic Charleston photo and a genuinely lovely spot to cool off. Even better at night when it’s lit up.
Charleston City Market
Pop into the Charleston City Market on your way back. Browse. Let yourself be tempted by local artisan works, including sweetgrass baskets — those handwoven beauties are priced by the hours it takes to make them, and the women who weave them are continuing a Gullah tradition that goes back centuries. Knowing that changes how you look at them. Faith told us this is mistakenly referred to as the old Slave Market instead of the old Slave’s Market. Slaves were never bought and sold here, but it was the market slaves would often come to, to buy or sell produce for their slave owners.
NOTE: If you are staying at the French Quarter Inn, feel peckish, and want a break in the sun before dinner, head to their free wine and cheese in the courtyard. I was quite impressed with the selection of cheese and snacks available.
Dinner: Rancho Lewis
I loved that dining at Rancho Lewis allowed us to wander outside the downtown area to experience a different side of culinary Charleston. Don’t let the West Texas theme throw you — chef John Lewis, owner of the legendary Lewis Barbeque, brings serious wood-fired skills and an interior design and menu that’s rooted in his El Paso upbringing. Unexpected for Charleston. Completely worth it.
Our menu picks (also recommended by our server): Queso Asado (signature and delicious) Smoked biscuit enchiladas, Rancho fajitas with steak, North Mesa Street Tacos, and a flan for dessert. Note: Their homemade corn tortillas were the best I’ve had outside of the maya tortillas I had in Belize AND almost everything on the menu can be made gluten free! Yay!
If you want to eat in downtown Charleston, Faith recommended these restaurants: 82 Queen, The Ordinary, The Darling Oyster Bar, La farfalle, Fleeting Landing on Water, and Magnolias (shrimp & grits)
Saturday Morning: The Food Tour You Actually Need to Take
The food tour does not start until 11am, so you can fill your morning with a sleep in, buffet breakfast at the hotel or at a local restaurant/cafe, more historic Charleston wanderings, or like Craig and I did, a bike ride through the French Quarter and the Battery, stopping at the local-not-touristy Second State Coffee for a break.
Charleston Food Walking Tour
Block out your whole morning for Bulldog Tours’ Savor the Flavors walking tour. This is not a “here’s a sample, now buy the cookbook” kind of food tour. This is two and a half hours of walking through the streets with a guide who treats the food as the lens through which you understand everything about Charleston — the Indigenous influence on grits and crops, the enslaved Africans who brought okra, boiled peanuts, and collard greens (and whose agricultural knowledge literally made the rice industry possible), the hurricanes and liquor law changes that shaped the modern restaurant scene.
Our guide Faith was extraordinary, part food historian, part storyteller, part warm human who made our teenager feel completely included. She explained how Hurricane Hugo in 1989, which pushed a 25-foot storm surge through the city and wiped out most of the chain restaurants, was inadvertently responsible for the incredible local food culture that exists today. The rebuilding left room for local hospitality to move in.
Savor the Flavor highlights along the way: biscuits with a history lesson attached (the South didn’t invent them but absolutely perfected them), pimento cheese made properly — sharp cheddar, Duke’s mayo, that’s it — the sustainability of Charleston’s oyster farming program, and she-crab soup, which was invented right here when a Charleston mayor told his butler to make crab soup for President Taft and told him to “make it fancy.” He added crab roe and sherry. Taft loved it enough that the recipe went straight to the White House.
Don’t worry if you have a dietary restriction, I am gluten free, and a fellow tourist was seafood free, and we were adequately catered to. The BBQ pork sampled at Poogan’s BBQ (yes that Poogan) was some of the best I’ve ever had! Craig and Savannah loved their fried chicken biscuit with Tasso gravy at Ruby Slippers. I came home with a bag of spices and creamy tomato soup mix (thanks to that tasting) at the Spice and Tae Exchange where we ended the tour! By the time you finish, you’ll understand Charleston in a way that no museum can give you. Check tour availability.
Saturday Afternoon: Stories on Horseback and Rooftops at Sunset
Horse-Drawn Carriage Tour
Old South Carriage Company does what it sounds like — horse-drawn carriage tours through the historic district — but don’t dismiss it as a tourist cliché. The guides are Palmetto Guild Certified, the Belgian and Percheron horses are genuinely well looked-after (they have a 110-acre farm called “Horse Heaven” for rest days), and the architecture hits differently when you’re moving slowly through it at horse pace.
We learned that 40% of the city is built on reclaimed land, that the church steeple of St. Michael’s Anglican leans slightly from the 1886 earthquake (the second most seismically active fault line on the East Coast, apparently — who knew), and that the narrow shape of those single-style homes reduces interior temperature by 10-15 degrees without any air conditioning. The city was an engineering comfort centuries before HVAC existed.
Our guide Emerson had a gentle and friendly personality, and balanced wit with cliché jokes throughout his engaging story telling. His horse, ACE, was simply adorable and I loved giving him a gentle neck gratitude scratch after. Check tour availability.
Sunset Dinner: Difficult Choices
Since you’re probably only staying in Charleston for two nights, your dinner decision tonight may be difficult. We recommend heading to a rooftop to take in sunset views of Charleston. It is known as the Holy City with over 400 churches, see how many you can count from your rooftop view. Here are the two rooftop sunset view restaurants we experienced:
The Rooftop at Vendue Inn
The Rooftop at Vendue has been voted Best Rooftop Bar by Charleston City Paper since 2007. Live music, casual vibe, and a view of the harbor that makes you want to stay until dark. It’s very casual and feels more local. The menu is small and more bar style with tacos, burgers, salads, lobster roll, and steak frites. (Limited if gluten free).
The sunset views are beautiful with the iconic St Phillip’s steeple featuring prominently. Another wonder to enjoy here is the exceptional art gallery on display inside the Vendue Art Hotel on the ground floor on the way to the rooftop elevator. Wow that was a Charleston surprise!
The Watch Rooftop Kitchen & Spirits
The Watch Rooftop Kitchen and Spirits is located at The Restoration Hotel, just off King St. Farm-to-table, Lowcountry staples, panoramic views. On one side is the harbor and the other sunset views over the city. We recommend this side. The prominent steeple here is Grace Episcopal Church. The food and ambiance here was more elevated. On our plates: Sweet & spicy dry rub buffalo wings and deviled eggs for shareables; braised duck tagliatelle, sriracha teriyaki glazed chicken, and shrimp and chorizo bowl for mains.
Note: Charleston Gold Rice was the crop that made Charleston so wealthy. It is now a gourmet rice – hard to find and expensive and has a different flavor profile to normal rice – rich, buttery and nutty. You can’t come to Charleston and not eat it. Savannah and I were stoked that it came with our dishes.
SUNSET DINNER VERDICT: For its all-round experience, The Watch is the sunset rooftop restaurant we would recommend for you. If you can squeeze in a pre-dinner drink to enjoy different views from the Vendue Inn, I would do that! Decisions are difficult in Charleston.
Carmella’s Cafe and Dessert Bar
Cap the night at Carmella’s Cafe and Dessert Bar on East Bay Street in Restaurant Row— open until midnight, with lots of gluten-free options, and serving gelato, sorbet, and desserts that feel like someone’s grandmother’s best recipes with a gourmet twist. Order something you wouldn’t normally order. Be warned Carmella’s is popular and a line may snake out the door, but it moves quickly! Why not pair a dessert with a late-night cocktail? We capped up an extraordinary Charleston food experience with a gluten free raspberry tart, berry cheesecake, and cannoli!
Sunday Morning: Biscuits First, Then the Road
Callie’s Hot Little Biscuit
Carrie Morey started with her mother Callie’s recipe — a bite-sized biscuit made with country ham, Dijon mustard, and butter that became a made-in-Charleston sensation and ended up in Saveur, Food & Wine, and The New York Times. The biscuits are absurdly good. Get several. Callie’s Hot Little Biscuit has two locations: King St and the City Market. Both are more grab and go style (which I love!), but King St does have a small seating area. They have a variety of biscuits with sweet and savory fillings, mini biscuits perfect for sampling, as well as grits and bowls.
They have gluten free biscuits which made me so happy – they were buttery and delicious made even more so by the bacon, egg, and pimento cheese filling. It’s the south y’all! I was fascinated to hear the story that the owner, her mother, and her daughter all have the name Caroline – like me. But unlike me, they came up with Carrie and Callie as iterations. Mine? Caz and Ca.
King St Wanderings
Spend your remaining time on King Street — coffee at Kudu Coffee (lovely outdoor garden, more local crowd), and if you have teenagers in tow, King Street is the best shopping stretch in the city with big name brands and local boutique stores. It’s a pretty street to walk down and is buzzing with activity.
Another cafe worth mentioning is Hidden House. tucked away off King St. The coffee wasn’t as great as the other cafes, but still decent. You will delight in its setting inside an old house! (Also, a wine bar of you prefer that!)
Ashley River Road Estates
On the drive home to Raleigh, if you have an hour to spare, the Ashley River Road is worth the detour. We stopped at Magnolia Plantation and Gardens (spring gardens are gorgeous) and Drayton Hall — the only original plantation house still standing in the area, now a working archaeological site.
Dayton Hall is mostly empty inside, which makes it more haunting than most finished houses. Historians work there daily to preserve what’s left. I did originally want to go to Middleton Place but somehow ended up at Magnolia. I still haven’t figured out what went wrong.
Worth Your Time (If You’re Staying Longer)
These additional tours below are worth your time if staying longer. We have a 4 day Charleston itinerary on our travel blog.
Gullah Tours with Alfonso Brown
Alfonso, owner of Gullah Tours, is passionate, funny, high-energy, and will teach you things about Charleston’s history — the language, the culture, the cuisine, the ironwork gates made by master blacksmith Philip Simmons, the creation of ketchup — that you will not find anywhere else. We stood by the Anson Street African Burial Memorial, where recent fountain renovations uncovered graves of enslaved and free people — a circle of hands reaching upward from the water fountain.
The Gullah people were descendants of enslaved Africans who settled on the Lowcountry barrier islands and developed their own language, a creole blend of English, French, Portuguese, and West African languages. “Kumbaya,” it turns out, is a Gullah word. It means “come by here.”
Alfonso will also tell you that “kombiyah” is what happened when people were trying to communicate across language barriers — and that feels like the most Charleston thing possible. A city built on collision and survival, where the food, the language, and the architecture all carry the weight of that history in the same breath as the beauty. It’s an eye-opening Charleston tour that will, like the Old Slave Mart, deepen your understanding of the African American story.
Note: At times it can be a challenge to understand Alfonso, but he will repeat it and explain the Gullah language he infuses along the way. You will spend most of the time inside a bus, and there is a lot of information to take in, so it may not be a good choice for younger kids.
Go Down a History Rabbit Hole
Consider adding the Old Exchange & Provost Dungeon to your day (recommended by several in our Facebook community). It sits beneath the Old Exchange Building — the same grand structure where the Declaration of Independence was read aloud to Charlestonians on July 4th, 1776. Below it, British officers imprisoned Continental Army soldiers in conditions that are difficult to hear about and impossible to forget. The dungeon was also where tea tax contraband sat for years until the British could collect payment — a small footnote to the Boston Tea Party narrative we all learned in school.
The Exchange building was also where George Washington danced through two pairs of shoes when he visited in 1791. You can see the Great Hall upstairs where this happened! History here layers like that, the profound and the playful sitting right next to each other.
The Logistics
- Getting there from Raleigh: About 4.5 hours on I-40 E to I-26 S. Easy drive, worth every minute.
- Where to stay: French Quarter is a good district for a splurge. Check out this cool loft in the French Quarter. Plenty of good options on King Street for every budget.
- Don’t miss: The Charleston Tour Pass gives access to 40+ attractions and is a great way to save money on Charleston attractions.
- Eat and drink: Rancho Lewis, The Watch Rooftop, Carmella’s, Callie’s Biscuit, Harken Coffee, Kudu Coffee. Add Poogans Porch and Poogan’s Smokehouse if you have extra time — the pulled pork sliders and skillet cornbread are the real deal.
- For the history lovers: Bulldog Tours food tour, Provost Dungeon, Gullah Tours, Old Slave Mart.
Map of Charleston Experiences
To use the map below, Click the top right button to open it in a full page. From there, click the top left drop down to make a copy of the map. Then you can adjust it as needed for your personal use. Or click the star next to the map, to add it to your Google Maps account. You’ll then find it under Your Places on the menu tab in google maps.
Charleston is the kind of city that rewards curiosity. Go hungry — for food, for history, for stories. It will not let you down. Have you been to Charleston from Raleigh? What’s your must-do? Drop it in the comments — I’d love to know what I missed.
Frequently Asked Questions About Visiting Charleston from Raleigh
How far is Charleston from Raleigh?
Charleston is roughly 5.5 hours from Raleigh via I-40 East to I-26 South. It’s an easy, mostly highway drive with plenty of good stops along the way if you want to break it up. Put on a good podcast and it goes quickly.
How many days do you need in Charleston?
Two full days gives you a solid trip if you plan well — which is exactly what this guide is for. Three days lets you breathe a little more, catch a day trip to Folly Beach or Kiawah Island, and linger over meals instead of rushing through them. Four days (what we had) and you’re starting to feel like a local. Honestly, there’s no version of this trip that feels too long.
Is parking difficult in Charleston?
It can be. Downtown parking is limited and fills up fast, especially on weekends. Our honest advice: stay somewhere central (as we did at the French Quarter Inn), park once when you arrive, and walk or grab an Uber for anything further afield. There are parking garages near the Visitor Center on Meeting Street and near the City Market, but factor in the cost — downtown garage parking adds up over a weekend. If you’re day tripping, arriving early makes a real difference. (Our parking garage cost $24 a night)
Do I need to book restaurants in advance?
For the popular spots — yes, and don’t leave it too late. Poogan’s Porch, The Watch Rooftop, and Rancho Lewis all book up, especially on Friday and Saturday nights. I’d recommend locking in dinner reservations at least a week ahead for a weekend visit. Lunch tends to be more forgiving.
Is Charleston good for families?
Really good, actually. The history is accessible for kids at almost every age, the food scene has something for everyone, and the carriage tours, City Market, Waterfront Park, and the South Carolina Aquarium all work well with younger visitors. Our teenager had a genuinely great time — which, as any parent knows, is not always a given on a history-heavy trip.
What is the best time of year to visit Charleston?
Spring is magical — azaleas blooming, mild temperatures, the city at its most photogenic. We visited in late March/early April and it was perfect. Fall is equally lovely. Summer is hot and humid in a way that requires respect, and hurricane season runs June through November. Winter is mild by most standards, though some attractions run reduced hours.
Is the Bulldog Tours food tour worth it
One of the best things we did on the entire trip — and I don’t say that lightly. It’s two and a half hours, but it goes fast because the stories are so good. If you only do one structured activity in Charleston, make it this one. Book ahead as spots are limited.
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