5 Days in Charleston Itinerary: History, Charm & Biscuits
Two things I love about Charleston: the food and the history. Add to that the scent of salt air drifting in from the harbor, Spanish moss swaying like lace curtains, and the kind of Southern charm that makes strangers call you “darlin’,” and this city keeps climbing my list of places I could happily retire. When unforeseen circumstances canceled our Panama trip, The Hubs and I turned disappointment into an excuse for a return to Charleston.
December in Charleston wasn’t exactly beach weather; it hovered in the 50s, crisp enough for a jacket but still better than shoveling snow in upstate New York. This time, instead of a chain hotel, we stayed at the John Rutledge House Inn, one of the city’s 18th-century mansions turned boutique inn. Mornings began with silver trays of warm breakfast (coffee mugs hot in our hands, eggs fragrant with herbs), afternoons paused with tea and petite cakes, and evenings ended by the crackle of a fire while rain tapped at the windows. It was the kind of stay that made the whole trip feel slower, softer, and deeply steeped in place.
Day One: Biscuits, Baby Donuts & A Cemetery That Breathes History
We set out for the City Market, where the air carried the earthy sweetness of sweetgrass baskets mingling with roasted peanuts. Since the 1790s, these market sheds have been Charleston’s heart.
Our “late breakfast” at Callie’s Hot Little Biscuit was flaky, buttery, and steaming in the cold air, the kind of biscuit that leaves your fingers greasy in the best way. The smell of butter had lured us in from half a block away. The baby donuts were so tiny they disappeared in a pop—warm and sweet, powdered sugar melting on our lips like snowflakes that didn’t stand a chance. By the time we left, a dusting of sugar still clung to my coat sleeve like confetti.
After we finishThe Old Charleston Jail came next, a hulking gray building whose heavy stone seemed to echo with clanging iron doors even though the place stood silent.
From there we slipped into the Unitarian Churchyard, where the ground is carpeted in ivy, the air damp and earthy. Birds flitted between wild vines, and the crunch of gravel underfoot was the only sound. It felt less like a graveyard than a secret woodland, holding its stories close.
That evening, the Aiken-Rhett House greeted us with creaking floors and faded wallpaper, a preserved time capsule. You could almost feel the cool plaster walls and the weight of history lingering in its emptiness.
Dinner at Prohibition had its own atmosphere: dim lights, clinking glasses, and the perfume of citrus and herbs rising from cocktails. The tuna crudo was cool and delicate, a bright counterpoint to the December chill outside.
Day Two: Cannons, Sea Oats & A Meal for the Books
Crossing the bridge to Sullivan’s Island, the briny scent of saltwater thickened in the air. At Fort Moultrie, gulls screamed overhead as cannons sat silently aimed toward Fort Sumter. Wind whipped across the parade ground, carrying the faint metallic tang of rust from old iron. Standing there, you could almost hear the imagined boom of cannon fire and the crack of sails in the harbor.
The Sullivan’s Island Nature Trail softened things: sand under our shoes, pine needles crunching, and the whisper of sea oats bending with the breeze. The ocean appeared suddenly, wide and foamy, waves collapsing with a rhythmic hush.
Dinner at The Obstinate Daughter was our highlight meal. The sharp brine of oysters gave way to the smoky char of octopus, pizza crust crackling between bites, and a crème brûlée whose caramel top cracked under the spoon with a satisfying snap. The scent of bourbon and toasted pecans lingered long after the plates were cleared.
Day Three: Confronting the Past, Ending with Gelato
The air inside the Old Slave Mart Museum was still and cool, carrying only the rustle of paper as visitors read the sobering exhibits. Words and photographs told Charleston’s role in the slave trade in a way that made the silence feel heavy. A few blocks away, the Old Exchange & Provost Dungeon smelled faintly of stone and damp earth, its underground rooms echoing with imagined footsteps.
We lightened the afternoon with a stop at Belgian Gelato. The scent of waffles and sugar wafted out the door, and we ordered gelato that melted faster than we could keep up. Powdered-sugar poffertjes arrived warm and chewy, the sweetness sticking to our fingers. We ate them near the Pineapple Fountain, where children splashed in sprays of water, laughter bouncing against stone. Around the corner, Rainbow Row glowed in pastel shades that looked even brighter against the gray winter sky.
Dinner at Fleet Landing gave us the taste of the sea one more time: she-crab soup rich and creamy, the soft crunch of crab cake on top, the faint salt of fried shrimp. The hush puppies disappointed, but the waves lapping against the pier outside carried the evening.
Day Four: Cupcakes, College Pride & Porch Dining
The Nathaniel Russell House felt like stepping into a jewel box: polished wood underfoot, the sweeping spiral staircase pulling your eyes upward in awe. The rooms smelled faintly of beeswax and old books, a sharp contrast to the peeling walls of the Aiken-Rhett House.
We wandered the College of Charleston campus, where oak branches creaked overhead and brick walkways radiated the day’s warmth back into the cool night. At Sugar Bakeshop, we hoped for red velvet cupcakes, but left with buttery cookies whose sweetness perfumed the bag until they were gone.
Dinner at Poogan’s Porch brought its own sensory indulgence: the crunch of fried green tomatoes under the fork, pimento cheese melting slightly against bacon jam, the comforting heft of she-crab soup. The dining room creaked with every footstep, a reminder that these old houses hold life in their bones.
Day Five: Gardens, Giants & A Final Oyster Toast
At Middleton Place, the air was sharp with winter greenery, and the crunch of gravel paths echoed under our shoes. Pools mirrored gray skies, and trimmed hedges stood in precise lines. Then came the moment: a bald eagle landing with a rush of wings on an ancient oak, the sound startlingly loud in the quiet garden.
Lunch at Boxcar Betty’s smelled of fried chicken and hot oil, the sandwich dripping down my wrist as I leaned over to keep it from falling. Sauces for the fries ranged from smoky to tangy, and we sampled them all, laughing at our mess.
We detoured to the Angel Oak Tree, where the air was damp and earthy, cool even in daylight. Its limbs touched the ground like resting giants, rough bark under fingertips. Beneath it, I felt very small—and very lucky.
Our final stop was The Darling Oyster Bar, buzzing with chatter, ice clinking into glasses. The briny chill of raw oysters and the citrus bite of ceviche tasted like celebration. The room smelled faintly of sea spray and lemon zest, a modern Charleston finale after days of layered history.
Reflections on Charleston
Charleston lingers long after you leave, not just in the pounds gained (four, in my case) but in the way the city seeps into your senses. I can still smell the buttery warmth of biscuits, feel the grit of sand in my shoes from Sullivan’s Island, and hear the creak of wood floors in centuries-old houses. Somewhere in memory, too, lingers the clip-clop of carriage wheels on cobblestones and the low murmur of the harbor at night. The salty sting of oysters and the sweetness of a pecan bourbon crème brûlée live side by side in memory, just as pastel houses coexist with haunted cemeteries.
I hope this inspires you to travel, to eat, and to join me as I continue sharing my journey through seven continents and infinite foods.
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If You Go – Quick Itinerary
Day 1:
City Market
Charleston Jail
Unitarian churchyard
King Steet
Prohibition (takes reservations)
Day 2:
Obstinate Daughter (takes reservations 2 weeks out)
Day 3:
Belgian Gelato
Waterfront Park
Rainbow Row
Fleet Landing (takes reservations)
Day 4:
The Battery
White Point Garden
Poogan’s Porch (takes reservations)
Day 5:
Angel Oak
The Darling Oyster Bar (takes reservations)
**I would highly recommend that you make reservations in advance when available. I always book scheduled activities and typically make dinner reservations in advance. I’ve indicated with a parenthetical any restaurants that take reservations.