We were introduced to Charleston by a family friend, Rahim, following his graduation from med-school. At the time, we couldnt help but imagine Charleston as our future retirement home or the site of a wedding. Well, we were married in Charleston, SC and fell in love with the city ever since. You'll love Charleston's historic architecture, amazing southern cuisine, and island hopping across the east coast's best beaches.
Day 1: The Old Soul of the City — Where Time Moves Slow and the Air Sticks to You
Charleston’s not about speed. It’s about soaking — in history, in humidity, in butter and bourbon.
Historic Charleston - Charleston is one of America's most beautiful colonial cities. Start with a walk through the heart of the city — cobblestones underfoot, iron balconies overhead, and oak trees draped in Spanish moss. Skip the guided tours; just wander. The city’s old homes whisper stories if you slow down long enough to listen.
Poogan’s Porch - Tucked inside a Victorian house on Queen Street, this is classic Charleston comfort with polish — fried green tomatoes, shrimp and grits, biscuits so soft you could sleep on them. Or, try the Chicken and Waffles, Shrimp and Grits, or Sweet Tea glazed Salmon. The ghost stories are real, or at least believable after a sweet tea or two.
Charleston City Market - This 200 year-old market has shifted from the classic shopping destination for locals to one of Charleston's top tourist traps. Yet, the City Market is a fun place to explore local food vendors and arts and crafts. We can't visit Charleston without stopping for praline pecans! Browse sweetgrass baskets woven by Gullah artisans, taste local hot sauces, and eavesdrop on conversations that blend old Charleston drawl with new Southern energy.
Husk - The kind of restaurant that made Charleston a culinary capital. Sean Brock’s philosophy: if it ain’t Southern, it ain’t on the plate. Try any of their delicious dishes on a rotating menu like Teriyaki Glazed Pig’s Ear Lettuce Wraps, Southern Fried Chicken Skin with Ranch Pimento, Heritage Pork, or the Carolina Catfish — food with roots, cooked with reverence. Also, try the Bar at Husk, a speakeasy style watering hole, just next door, while you wait for your table.
Day 2: Rivers, Roots, and Real BBQ Smoke
You can dress Charleston up, but it still smells faintly of smoke and salt — and that’s a compliment.
Mozzo Deli - The lines at Mozzo Deli tell the story. The food is amazing and locals travel from Charleston and surrounding cities travel near and far to taste it. Locals swear by Mozzo’s, but and never tell tourists about it. Yes, delis are everywhere- in cities all over America. But, this one is special. Their bagels just taste better. Their sandwiches are unique, healthy, and still taste great. It’s a must visit when in Charleston.
Boone Hall Plantation - A visit to Boone Hall is a visit through history. The Boone Hall marsh and surrounding gardens is undeniably beauiful. However, a visit is both uncomfortable and important as you digest the colonial hall and plantation that was a historically important part of Charleston's history through the era of slavery in America.
James Island County Park
Go where locals go to breathe. Walk shaded trails, spot herons and egrets, and remember this city’s connection to the marshes that shaped it. The beauty here is slow, subtle, and everywhere.Palmetto Brewing Co. - Charleston’s oldest brewery — industrial, honest, and local through and through. Grab a pale ale, listen to live music, and talk to someone at the bar. Everyone’s got a story, and most of them start with beer. If the image tells the story, we had a good evening at Palmetto Brewery. Actually, we took it easy at what we would consider to be Charleston's top brewery. But, we had to show-off Palmetto Brewery's unique bathroom works of art. Now, onto the beer. You won't be disappointed. We enjoyed several of Palmetto's unique brews while playing corn hole in the front lawn.
Day 3: The Water, the Wind, and the Whisper of Salt
You don’t fight Charleston’s coastal air. You surrender to it — salty, sticky, and alive.
Sullivan’s Island or Folly Beach - Pick your mood. Sullivan’s is calm and quiet — a morning walk, barefoot in cool sand. Folly Beach is louder, looser — surfers, dive bars, and shrimp tacos. Either way, the Atlantic’s got something to say if you’re listening.
Fleet Landing Restaurant & Bar - Right on the waterfront, it’s one of the few spots where you can actually eat over the harbor. Fried oysters, she-crab soup, cold local beer. Simple food, done right. Watch the boats drift by, and let time do the same. We definately rcommend the Whole Fried Southern Flounder with appricot glaze. The She-Crab Soup w/ Blue Crab Roe & Sherry a great starter as well!
Waterfront Park - Grab an ice cream, find a bench, and stare at the Pineapple Fountain — a symbol of Southern hospitality that feels both sincere and a little ironic in the heat. Kids splash, couples pose, and the breeze from the Cooper River gives you a moment of peace.
The Cocktail Club - Upstairs on King Street, this is Charleston’s nightcap temple — dim lights, wood, and whiskey. The cocktail club is the perfect way to spend your night in Charleston. It was actually the location for a night of fun on the eve of our wedding. You'll love the old speakeasy lounge furniture while listening to good music and while sampling carefully crafted cocktails. Try the “Southern Gentleman,” a bourbon cocktail with black tea and lemon. It tastes like a quiet rebellion against everything proper.
Day 4: Modern Charleston — Where Tradition Gets Rewritten
By now, the city’s gotten under your skin — part old South, part new world, and all heart.
The Daily - A modern café that feels like the city’s evolution in motion — avocado toast meets cold brew, but with grits on the side just in case anyone forgets where they are.
King Street Stroll - King Street is Charleston’s pulse — part luxury, part grit. Check out Blue Bicycle Books, then stop by a few art galleries tucked between boutiques and bars. Don’t rush — Charleston doesn’t like when you rush.
The Ordinary - End with seafood that honors the Lowcountry’s bounty without the fuss. Raw bar, oysters, shrimp ceviche, local fish — all served in an old bank building that feels both timeless and alive. Raise a glass to the sea that fed this city and the people who still keep it honest.
The Gin Joint - This may be my favorite bar/lounge in America right now! The setting is inspired by a 1920s speakeasy. More importantly, Gin Joint makes drinks customized to your taste. Just tell them if you like sweet, spicy, bold, smoky or a combination and you wont be disappointed.
