A Guide to a Dreamy Week in Charleston

If you’re looking for a city that oozes Southern charm, drips in history, and has the kind of food that will make you consider moving there permanently, Charleston is calling your name. I visited in early May, and let me tell you, it was perfect. Warm but not humid, sunny but not scorching—ideal for wandering through cobblestone streets, pastel-colored homes, and waterfront views. This is your guide to spending a week soaking in Charleston’s beauty, history, and, most importantly, its insanely good food.

Strolling Through Charleston’s Historic Neighborhoods

Charleston is a city best explored on foot, so get ready to rack up those steps. Walking through neighborhoods like the French Quarter and South of Broad feels like stepping back in time. The rainbow-hued facades of Rainbow Row, iron-wrought balconies, and charming window boxes bursting with flowers make this one of the most picturesque places in the country. Every street has a story—if only these centuries-old mansions could spill the tea! As you wander, take a moment to appreciate the layers of history, the lives lived here, and the resilience of this city through centuries of change.

The Waterfront: East Battery Street & Waterfront Park

A walk along East Battery Street is a must. This stretch offers some of the best views of the Charleston Harbor, framed by grand antebellum mansions that make you wonder what life was like here centuries ago. The salt air, the gentle rustling of palm trees—there’s a certain poetry to this place.

Then, head over to Waterfront Park, home to the famous Pineapple Fountain—one of the most photographed spots in Charleston. Grab a bench, listen to the water trickle, and soak in the coastal breeze—it’s a moment of pure serenity amidst your explorations, a perfect pause to reflect on the city’s past and present.

A Free Walking Tour Through Charleston’s Rich History

Charleston has no shortage of history, and a free walking tour is one of the best ways to dive into its past. Led by knowledgeable locals, these tours take you through the city’s most significant sites while sharing stories of Charleston’s colonial beginnings, its role in the Civil War, and its architectural evolution. As you listen, imagine the footsteps of those who came before you, each street echoing with stories of triumph and tragedy. Plus, they’re free (though tipping your guide is always a good idea), making this an excellent budget-friendly activity!

Biking Through Mount Pleasant

Head over to Mount Pleasant and rent an e-bike at Rebellion Roads E-Bike Tours, Rentals, & Repair Shop—trust me, it’s worth it. Ride along the scenic Pitt Street Bridge, a hidden gem offering stunning waterfront views and a peaceful retreat from the city bustle. Then, cruise through the charming neighborhoods of Mount Pleasant, where grand oak trees and classic Southern homes create a dreamy backdrop. Continue your ride to Shem Creek Marina, where you can spot dolphins playing in the water and shrimp boats docked along the boardwalk.

After soaking in the beauty of Mount Pleasant, hop back in the car and drive across the Ben Sawyer Bridge to Sullivan’s Island. This quiet beach town is the perfect place to slow down and breathe in the salty air. Stop for lunch at Poe’s Tavern, a quirky and beloved spot dedicated to Edgar Allan Poe, where the fish tacos and burgers are legendary. End the afternoon exploring Fort Sumter and Fort Moultrie National Historical Park, where the echoes of history remind you of Charleston’s past and its role in shaping the nation.

Ferry to Fort Sumter & Exploring Fort Moultrie

For a deep dive into Charleston’s Civil War history, take the ferry to Fort Sumter National Monument. This is where the first shots of the Civil War rang out, marking a pivotal moment in American history. The boat ride over offers spectacular views of the Charleston Harbor, and once you arrive, you’ll walk through well-preserved ruins that tell the story of the fort’s role in the war. Rangers provide insightful talks, and exhibits bring history to life. Standing here, with the wind whipping off the water, it’s easy to imagine the tension and drama that unfolded on these very grounds over 160 years ago.

A Step Back in Time at Middleton Place

If you love sprawling gardens and historic estates, Middleton Place is a dream. The landscaped gardens are some of the oldest in America, but beyond the beauty, this visit is a humbling one. Middleton Place was a plantation, and it’s important to engage with the history of those who lived and labored here. Take time to learn about the enslaved people who built this estate through the site’s educational exhibits and guided tours—it’s a necessary step in truly understanding Charleston’s layered past.

For an even deeper look into life on the plantation, visit the Stableyards. This living history exhibit offers a glimpse into the working farm, complete with heritage breeds of sheep, cows, and horses. Watch skilled craftspeople demonstrate blacksmithing, pottery, and other trades that were essential to plantation life. Walking through the stable yards, you can feel the past come alive, a powerful reminder of the generations who shaped this land.

Shopping at Charleston City Market & King Street

No trip to Charleston is complete without some shopping. The Charleston City Market is the place to find local crafts, including sweetgrass baskets woven by Gullah artisans—a tradition passed down for generations. As you browse the market stalls, think of the history behind these crafts and the hands that have kept these traditions alive. For more upscale and trendy finds, King Street is where it’s at—boutiques, high-end brands, and cute cafés line this famous shopping street. Whether you’re looking for souvenirs or just window shopping, these spots are a treat.

Old Slave Mart Museum: A Somber but Necessary Visit

Charleston’s beauty is undeniable, but it’s important to acknowledge its dark history as well. The Old Slave Mart Museum is a small but powerful museum located in what was once a slave auction house. The exhibits are deeply moving, offering firsthand accounts and historical documents that shed light on the realities of slavery in Charleston. As you stand within these walls, remember the lives impacted here. It’s not an easy visit, but it’s an essential one for understanding the full history of this city.

Let’s Talk About the Food (AKA Heaven on a Plate)

Charleston is legendary for its food, and you’d be doing yourself a disservice if you didn’t indulge. My absolute favorite restaurant? Magnolias—hands down, one of the best meals I’ve ever had. Think upscale Southern comfort food that will leave you speechless (get the fried chicken or shrimp and grits!). While I did a food tour, it wasn’t as impressive as I expected—honestly, just hopping from restaurant to restaurant on your own is the way to go. Other must-eats: Husk (for locally sourced, innovative Southern dishes), Leon’s Oyster Shop (for crispy fried chicken and fresh oysters), and Callie’s Hot Little Biscuit (because you need a good biscuit in Charleston).

Charleston is a city that invites you to slow down, wander aimlessly, and soak in its charm. Whether you’re strolling through historic streets, learning about its layered past, biking by the water, or indulging in some of the best food the South has to offer, this city is a solo traveler’s dream. But don’t just see Charleston—feel it. Let its history humble you, its beauty enchant you, and its spirit stay with you long after you leave. Pack your cutest sundress, bring comfy shoes, and get ready to fall in love with Charleston—because trust me, you will.