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A note: Our Charleston trip was hosted in partnership with Explore Charleston, who provided our itinerary, accommodation, and access to tours. As always, all opinions — and every rabbit hole we tumbled down — are our own.
Craig and I first fell in love with Charleston years ago — before kids, before yTravel Blog, when we were traveling on the kind of budget that meant a horse and carriage ride was basically the splurge.
We didn’t do much beyond wander the streets and gawk at the homes, but that was enough. Charleston got us. It became one of our favorite cities in the US, and honestly, it’s one of the quiet drawcards of living in Raleigh — the knowledge that this place is just under four hours away whenever we need it.
This trip was different. Craig, Savannah, and I came back with time, with intention, and with the kind of access that lets you dig into a city rather than just admire it from the outside. We did the food tour. We did the Gullah tour. We drove the Ashley River Road on the way home. We went back to the same coffee shop twice because it was that good.
What we found was a city of extraordinary layers — culinary, historical, architectural, deeply human — and a place that tells its own story honestly, including the parts that are difficult to hear.
Charleston surprised us all over again,. We loved how three nights/ four days allowed us to hit the tourist spots but balance that with slow wanderings, café bumming, morning bike rides, and beyond the surface discoveries. Here’s how to make the most of four days.
Practical Details Before You Go
Getting There:
Charleston is in South Carolina on the east coast. It’s at the end of Hwy26 which meets the I95. It’s two hours from Savannah and Myrtle Beach, and four and a half hours from Raleigh. If you’re flying, Charleston International Airport (CHS) has direct connections from most major US cities.
When to Go: Spring (March–May) is stunning — warm, flowering, and before the heavy summer humidity sets in. We visited in late March, and the azaleas were in bloom everywhere and the jasmine was about to arrive. Note that Charleston floods on full moon high tides — water comes up through storm drains and can reach knee depth in spots. It’s interesting rather than alarming, but worth knowing.
Budget Notes: Charleston skews upscale, especially for dining and accommodation. Budget travelers can manage by choosing a few splurge experiences (the food tour is worth every cent) and using free time wisely — the walking, the battery, the market, the dock theatre are all free or nearly so. The Charleston Tour Pass gives access to 40+ attractions, museums, and historic houses, at a price that helps you save 40% on attraction prices. It is an excellent value if you plan to explore the city deeply.
Getting Around: You genuinely don’t need a car once you’re in the historic district. We walked most of the city, the hotel had bikes available (more on that), and Uber/Lyft can fill any gap if you need to. Traffic in Downtown Charleston is a headache with the narrow streets, horses and carriages, and pedestrians. Save the car for the drive home along the Ashley River Road — which we highly recommend. Check rates here if you need a rental car.
Where to Stay: We stayed at the French Quarter Inn on Church Street, and it set the tone for everything. Named a top 5 hotel in the US by TripAdvisor’s Travelers’ Choice Awards four years running, it’s a 50-room luxury boutique property in the heart of the historic district. What makes it feel special isn’t the thread count (though that’s excellent), it’s the daily artisanal breakfast, the wine and cheese pairing in the afternoon, milk and cookies and port at night, the excellent hospitality, and the turndown service with hand-crafted chocolates and a sleep pillow menu. See rates and availability.
Day 1: Arrive, Historic Strolls, Eat Well
Check-in: French Quarter Inn
Arrive, enjoy a complimentary glass of champagne, drop your bags, walk out the front door. You’re already in the middle of everything you came to see.
Lunch: Poogan’s Porch
Poogan’s Porch was mentioned on every tour we did and by our Raleigh Facebook community as a must-not-miss Charleston restaurant. So, we made it our first stop to savor proper Charleson cuisine like (famous) shrimp and grits, biscuits and gravy, and Lowcountry hash. But the star of our table was Savannah’s chicken and waffles with peaches and bourbon huckleberry syrup. Honestly?
It’s not just the food that makes this restaurant in an old house famous, but the little dog – Poogan – whose favorite spot was the porch of what had just become a restaurant (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.
Afternoon: Wander the French Quarter
The blocks immediately around the hotel are among the most architecturally significant in the city. Take yourself on a slow wander toward the Battery — the historic seawall at the southern tip of the peninsula where the Ashley and Cooper Rivers meet the Atlantic.
The homes flanking White Point Garden are extraordinary: Antebellum style, Queen Anne Victorian, Second Empire, all lined up along the water with their long narrow footprint (designed for air circulation in the heat, we’d later learn — one room wide to reduce temperature by 10–15 degrees).
Here is what we recommend including:
- Start with coffee at Harken Coffee. It became our go-to. We went twice in four days. Enough said.
- The pink French Huguenot Church, one of the most photographed buildings in the city.
- 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.
- Stop in at the Dock Street Theatre across the road. It’s free, self-guided, and genuinely beautiful inside — one of America’s oldest theatre buildings. Don’t rush it. But you only really need 5 mins.
- Tour a historic home (we couldn’t time it right, but had these on our radar) Included in the Charleston Tour Pass
- 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.
- Rainbow Row: Brush your hair, apply your lippy and head to East Bay Street for the obligatory photo in front of the 13 pastel-painted terrace homes.
- 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.
- Pop into the Charleston City Market. 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.
- Pop down cobblestone side streets and alleyways to gaze at more colorful rows of old homes. Philadelphia Alley near the Old Slave Mart is a good one!
- Consider Old Slave Mart & Exchange Building & Provost Dungeon if time (more below as we did them on different days)
Dinner: Rancho Lewis, 1503 King Street
Our first dinner surprised us. Rancho Lewis is the newer restaurant from John Lewis, the acclaimed pitmaster behind Lewis Barbecue — but here he’s riffing on his West Texas and New Mexico childhood rather than his Carolina BBQ credentials.
The atmosphere is warm and Western, the food is excellent, and it’s a good reminder that Charleston’s culinary scene is broader than Low Country tradition (though you’ll get plenty of that too). We loved how this took us out of the historic district for a more local Charleston experience.
What you don’t want to miss is their signature Queso Asado ( never had a queso like that before), their smoked brisket enchiladas and a flan to tie it all together! 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!
Day 2: The History Is in the Food
This is your big day. Don’t shortchange it. Wear stretchy pants.
Slow Start: Bike Ride
Since your first activity does not start until 11, you have several hours in the morning to fill in. Most attractions open at 10am so I recommend a leisurely snack-sized breakfast at the hotel (great buffet spread), or a gentle walk through the French Quarter (always a new alley to explore),
Craig and I snuck in an early morning bike ride (the hotel provides bikes) — cycling around the Battery before the streets filled up and stopping at Second State Coffee (they have pastries), which has more of a local neighborhood feel. If you can fit this in, do it. There’s something about Charleston at 7am that the rest of the day can’t quite replicate.
Morning: Bulldog Tours — Savor the Flavors Food Tour (11am, ~2.5 hours)
Book this. We cannot recommend the Savor the Flavors food tour highly enough.
Our guide Faith — a Charleston-born, Maine-wintered storyteller with the kind of warmth that makes a teenager feel genuinely included — spent two and a half hours walking us through the city’s food history, and what we got was something richer than any museum exhibit.
A few things we learned that genuinely changed how we tasted the food afterward:
Charleston’s culinary identity is deeply rooted in the contributions of enslaved people. More than half the city’s population was enslaved at various points in history, and it was their knowledge — of okra, boiled peanuts, collard greens, rice cultivation — that formed the backbone of what we now call Southern food. The collard green, indigenous to Greece, was brought to the Carolinas by enslaved Africans who carried seeds through their hair. The collard green, it turns out, cleanses salt from the soil — which helped rice grow. It took time to communicate this, and the Gullah language evolved in part out of the necessity of bridging multiple African languages and English. That “Kumbayah” we all know? It’s Gullah. It means “come by here.”
Carolina Gold Rice — the crop that made Charleston wealthy beyond almost any other crop combined — is too expensive to be found in most restaurants today. It was exported by the millions of pounds through the Exchange Building in the 1700s. Almost none of it is grown in Charleston now. After slavery ended, no one wanted to grow it — the fields attracted mosquitoes, alligators, snakes. The rice industry collapsed, and it survives only as a gourmet commodity in the Carolinas.
Hurricane Hugo, which hit in 1989 with a storm surge of 17–25 feet, wiped out most of the chain restaurants in the historic district. Local hospitality moved in during the rebuilding process, and the restaurant scene that grew up over the following decade and a half is the one you’re eating in now. Charleston has very few chains downtown. Johnson & Wales culinary school opened here, and South Carolina didn’t allow full liquor measures in restaurants until 2006. (Before that: two ounces maximum. No specialty cocktails.) The restaurant culture is almost entirely post-1989 in character.
We stopped at several spots along the way, fried chicken biscuits with Tasso gravy at Ruby Slipper (a rare chain and one we visited at Orange Beach Alabama) and Poogan’s Smokehouse (from the same family institution as Poogan’s Porch —, where Faith explained that in Charleston, BBQ means pulled pork unless otherwise specified. Full stop. Living in North Carolina means I have eaten a lot of pulled pork BBQ; this was one of my favorites.
A Charleston food tour must dip into the oyster story. It’s not on the menu as they’ve learned it often doesn’t slide down well. But you can learn about Charleston’s extraordinary sustainable oyster farming: harvested shells are bleached, returned to the water as substrate, and new oysters grow on them within three years. She-crab soup — the Lowcountry classic made with crab roe — was invented here when President Taft visited and his host’s butler was told to make crab soup, but fancier. The butler added roe and a splash of sherry. Taft loved it and it ended up on the White House menu.
The tour ended at The Spice & Tea Exchange in Charleston Market (next door to our hotel), a specialty spice store where we sampled the most life-changing pimento cheese — made with fresh-grated cheddar, Duke’s Mayonnaise (created in Greenville, SC, sugar-free since wartime rationing), a yummy tomato soup, and a house spice blend including dried datil pepper. We bought the soup mix and spice blend.
Faith was exceptional. Her knowledge, her warmth, her easy way of presenting the history honestly — including the painful parts — made this the highlight of the trip.
And if you have dietary concerns, you will be looked after. My gluten free body had something yummy to eat at every stop and a fellow no-seafood tourist was catered to! Just let them know in advance. See rates and availability here.
Afternoon: Old South Carriage Company (3:15pm)
After the food tour, a carriage ride is the perfect pace-shift. Our experienced guide Emerson was unhurried, genuinely knowledgeable, dry wit deployed with precision. He wasn’t performing a script; he was talking about a city he clearly loves.
The horses are Belgian and Percheron draft breeds — our horse, Ace, weighed around 2,000 pounds and had the placid confidence of an animal who knows he’s the most impressive thing in the room. I reaffirmed that after the tour with a neck scratch, The company owns a 110-acre farm where horses rest between duties and retire into equine therapy work. The city regulates their working hours, and it’s considered among the most regulated horse-and-carriage operations in the country. Learn how the Old South Carriage Company cares for the horses.
What we learned: about 40% of the city is built on landfill. A significant earthquake (7.2 magnitude) caused a church steeple to lean slightly — and the city is about 40 years overdue for another major quake, the second most active fault zone on the eastern seaboard. The cobblestone streets are made from ballast stones brought over on ships from the Thames. The homes along the Battery with “single house” style — one room wide, long piazzas facing southeast to catch the breeze — were built to survive without air conditioning in a climate that didn’t forgive poor design.
You never know what route you are going to get on the tours until you pull up the carriage up to the traffic control center! This is my fourth horse and carriage ride in Charleston, and I think I’ve had the same route almost every time! But I learn new perspectives and stories each time! See rates and availability here.
Evening: Vendue Inn Rooftop Bar (6:30pm)
The Rooftop at Vendue has been voted best rooftop bar in Charleston since 2007. The views of the church steeples and the harbor at sunset are worth the trip alone. Come for drinks and let the day settle.
The menu here leans more on the casual bar food side and is limited, especially if gluten free. An option is to enjoy sunset drinks here and some appetizers (the trio of dips is an option) and then cross the road to Magnolia’s for more upscale foodie dining. We had many recommendations from our This is Raleigh Facebook community for this iconic restaurant and news on the street is it has the best shrimp and grits in town – a Carolina classic!
Add in a bit of time before going up to the rooftop to enjoy the impressive art exhibitions on the bottom level of the Vendue Art Hotel. Almost more wow worthy than the sunset beside St Phillip’s Church steeple. Almost.
Day 3: The Soul of the City
Again, you have another slow start to the morning. We decided to walk 20 minutes along King St to our Gullah Tour check in, stopping at Hidden House along the way. Harken Coffee was better, but this was worth it for its stunning setting inside – you guessed it – a historic house, all modernized with swanky style. Also, doubles as a wine bar.
Morning: Gullah Tours (11am, ~2 hours)
If the food tour taught us Charleston’s culinary history, the Gullah tour taught us its soul.
Alphonso Brown leads this tour with the kind of passion and warmth that fills a street. He opened with a Gullah language lesson — a creole language with deep roots in West African languages, formally recognized in 1939 as linked to Sierra Leone. “Kumbaya” is Gullah. “Buckra” means white people, which Alphonso deployed with excellent comedic timing. “Anna” means “you all.” The Gullah people, descendants of enslaved Africans brought to the Carolina Lowcountry, developed a distinct culture, language, and cuisine that is woven into everything Charleston is.
We drove past the Philip Simmons Gate — an intricate ironwork fish gate around St. John’s Episcopal Church, made by the master ironworker whose work now hangs in the Smithsonian’s American History Museum. We passed the slave quarters at the Aiken-Rhett house, which still stands. 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.
Alphonso talked honestly about the complexity of Charleston’s history: free Black men of significant wealth, like the D. Reef family (one of the richest free men in the city, who owned land and rental properties and was exempt from the free Black man tax because his mother was Native American). The caste system. The origins of the Charleston dance. The whipping house and jail that’s now a haunted building no one wants to go into. The Daughters of the Confederacy who Alphonso credits with rewriting the history books (not in a good way). He said what needed to be said, without flinching, and with enormous love for the city.
One detail that stayed with us: the indigo blue painted on many Charleston porch ceilings and around doorframes — what’s called “haint blue” — comes from Gullah tradition. Blue was believed to ward off evil spirits. Something borrowed, something blue. It’s everywhere once you start looking.
Afternoon: Free time — King Street and the Market
King Street Shopping
King Street is excellent for shopping and people-watching. King St is one of Charleston’s major thoroughfares and a central hub for shopping, dining and entertainment. It features a mix of antique shops, local boutique stores, several local bookstores, and big-name brands. Of course, during our spring break visit, it was buzzing with teenage girls, especially Brandy Melville, which Savannah dragged us into.
We grabbed coffee at Kudu Coffee — worth it for the courtyard garden alone — before a late lunch at Port of Call Food & Brew near the City Market, a laid-back spot that was a perfect midafternoon meal with a teenager. I really enjoyed my starter bowl of chicken bog (#soCharleston) tasty, affordable ($10) and filling, but not too large!)
The Old Slave Mart Museum
The Old Slave Mart Museum doesn’t need long — maybe 45 minutes — but it earns its place in the itinerary. The history of the domestic slave trade through Charleston is confronting and important. Sullivan’s Island, just across the harbor, was the entry point for over 40% of all enslaved Africans brought to North America.
Housed in Ryan’s Mart, now the Old Slave Mart, where enslaved people were bought and sold, it tells the story of South Carolina’s slave trading history through a series of informative exhibits. The Old Slave Mart Charleston doesn’t look away from this, and you shouldn’t either.
Evening: The Watch Rooftop Kitchen & Spirits (6pm)
The Watch Rooftop Kitchen and Spirits is a farm-to-table upscale restaurant on the roof of The Restoration Hotel with 360-degree views of the city. The menu leans into Low Country staples with a Southern flair and the handcrafted cocktails (order The Irresponsible Jalapeño) are worth the post-2006 liquor law appreciation. This was our favorite dinner of the trip.
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. The buzz for Savannah and I was having Carolina rice as the base of our bowls. After learning so much about it on this Charleston visit it was great to taste this rare, gourmet, buttery and nutty rice. #sogood
The other buzz: panaramoic views over Charleston – this time sunset beside the Grace Episcopal Church steeple. And on the other side of the restuarant, Charleston harbor. Do the sunset steeple side.
After Dinner: Carmella’s Cafe and Dessert Bar (8pm)
Did I mention stretchy pants in this post yet? You’re about to find out just another reason why Charleston has become a Southern foodie haven.
Carmella’s Cafe and Dessert Bar on East Bay Street is open until midnight and the answer to every question you have about dessert. Gluten-free options throughout the menu. The gelato alone will bring you back.
My gluten free almond raspberry tart was delicious, and I totally forgot to save some for tomorrow. Craig’s cannoli and Savannah’s berry cheesecake did make the takeout box though – after their stomachs put up the entrance closed sign. If you’re in the mood, they also serve cocktails!
Day 4: Morning Light, Biscuits, and the Drive Home
Breakfast: Callie’s Hot Little Biscuit (8am)
Carrie Morey left investment banking to rescue her mother Callie’s biscuit recipe – filled with country ham, Dijon, and butter – and it became a Charleston sensation that’s appeared in Saveur, Food & Wine, the New York Times, and about a dozen other places that know good food.
Callie’s Hot Little Biscuit has a variety of biscuits with fillings as well as grits and bowls. I devoured their gluten free biscuit filled with 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.
To enjoy this even more, ride the bikes from the French Quarter Inn! They also have a location inside City Market (10 steps from the French Quarter Inn)
Morning: One more wander down under
If you haven’t done it yet, this is the morning for the Provost Dungeon beneath the Exchange Building — the story of pirates (Steve Bonnet and Blackbeard both have Charleston chapters), the Revolutionary War, the 42-day siege, the ratification of the Constitution. The half-moon battery was only uncovered by archaeologists relatively recently.
The building itself is where the Declaration of Independence was first read publicly in South Carolina on July 4, 1776. You can also go upstairs in the Exchange Building to learn more and see the Great Hall where George Washington wore through two pairs of shoes dancing at a party filled with 400 Charlestonians.
The Drive Home: Ashley River Road
Do not take the highway directly home. Instead, drive out along the Ashley River Road (SC Highway 61), one of the most beautiful stretches of road in the South. You’ll pass through a canopy of live oaks draped with Spanish moss — and you can stop at:
- Drayton Hall — the only original antebellum plantation house on the Ashley River still standing in its original form. The interior is deliberately unfurnished; it’s an active archaeological site with conservators working daily. History buffs will find it genuinely fascinating for exactly that reason.
- Magnolia Plantation and Gardens — the gardens are at their best in spring, and they have a lot of additional activities like train tours and boat rides along the Ashley River. Tours of the house book up quickly – we missed out and settled for a wander around the gardens and slave cabins.
- Middleton Place (slightly further along) is also worth considering (so I heard) if you have time. I intended to go here but somehow turned up to Magnolia Gardens — that’s what happens when you navigate by vibes rather than GPS. Progress.
The Honest Take
Charleston is one of those cities where the longer you stay, the more you understand there’s still more to learn. The food tour alone gave us a completely different lens for everything we ate afterward. The Gullah tour reframed the contribution of the African American slaves to the culture and prosperity of the South, the architecture, the ironwork, the painted porch ceilings, the layout of the streets. The carriage ride connected it all geographically.
Go with curiosity. Walk slowly. Ask questions. Eat the biscuit. Savor the sunsets.
Have you been to Charleston? I’d love to hear what you discovered — drop it in the comments below.
Quick Reference
| Where to Stay | French Quarter Inn, 166 Church Street |
| Best Coffee | Harken Coffee (twice), Kudu Coffee (for the garden), Second State Coffee (for the local feel), Hidden House (for unique surprise) |
| Don’t Miss Tours | Bulldog Tours food walk, Old South Carriage, Gullah Tours |
| Best Dinners | The Watch Rooftop; Rancho Lewis |
| Worth Your Time | Provost Dungeon, Old Slave Mart Museum, Dock Street Theatre (free) |
| Save Money | Walk, hotel breakfast & free wine & cheese, free attractions, Charleston Tour Pass |
| On the Way Home | Ashley River Road, Drayton Hall, Magnolia Plantation, Middleton Place |
| For Teens | Kudu Coffee courtyard, Port Call lunch, King St shopping, the food tour (Faith is great with all ages) |
Frequently Asked Questions About Visiting Charleston
Is Charleston worth visiting?
Genuinely one of the best cities in the US, and we don’t say that lightly after nearly 30 years of travel. The history is extraordinary, the food scene is exceptional, and the city tells its own story honestly — including the difficult chapters. It rewards slow, curious travel more than almost anywhere we’ve been.
What is the best area to stay in Charleston?
The historic French Quarter district puts you within walking distance of virtually everything — the Battery, King Street, the City Market, the best restaurants and tours. Staying here means you barely need to think about transport. You may want to stay in a cute historic home.
What is Charleston known for?
Its layered history (more Revolutionary War battles than any other state), its Gullah culture and language, its extraordinary food scene rooted in African and Indigenous culinary traditions, its antebellum architecture, and its concentration of churches — over 400, which is why it’s known as the Holy City.
Is Charleston good for families with teenagers?
Yes — more than you might expect. The food tour, carriage tour, and Gullah tour all work well for teens who are curious and engaged. King Street is great for shopping. Gibbes Museum of Art is great for art loving teens. Beaches are nearby. The history is presented honestly and accessibly, which makes for real conversations rather than just sightseeing.
What is Gullah culture?
The Gullah people are descendants of enslaved Africans brought to the South Carolina and Georgia Lowcountry, who developed a distinct language, culture, and cuisine. The Gullah language — a creole with deep roots in West African languages — was formally recognized in 1939 as linked to Sierra Leone. Gullah influence is woven through Charleston’s food, architecture, ironwork, and traditions. Taking a Gullah tour is one of the most meaningful things you can do in the city.
What should I eat in Charleston?
Shrimp and grits, she-crab soup (invented here), pulled pork BBQ, biscuits, pimento cheese, boiled peanuts, and anything with Carolina Gold Rice if you can find it. Save room for the gelato at Carmella’s.
