Four Days in Charleston and Beyond
Charleston is a place where Southern charm truly comes to life. Beyond the distinct accents, chivalry, and warm manners, the city offers an array of delightful experiences—from enchanting gardens and historic homes to scenic carriage rides through storied streets.
I arrived in Charleston in time for the annual History Festival (formerly the House and Garden Festival), a beloved spring event that celebrates the city’s rich history and stunning architecture. For the first part of my journey, I explored the old part of town, a perfect blend of old-world preservation and the city’s evolving beauty.
On the next leg, I headed south to Hilton Head Island, a former plantation hub known for its statuesque palm trees and pristine beaches. Here, I toured the beautiful island as well as the antebellum towns of Bluffton and Beaufort, where the past and present meet in a captivating way.
Where to Begin
For an unforgettable start to your trip, make your base downtown Charleston, where you can easily walk to most of the city’s iconic sites. I eschewed a car and took Uber to my hotel, the Andrew Pinckney Inn, where I could explore on foot. The Inn is conveniently situated near the Old City Market and the waterfront, and is the perfect spot to immerse yourself in Charleston’s quintessential charm. History buffs may recognize the Pinckney name from Charles Pinckney, a Founding Father and American diplomat, and Thomas Pinckney, a former governor of South Carolina. Andrew Pinckney, the inn’s namesake, was a distant relative.
As is tradition in maintaining the city’s history, the inn is housed in two restored buildings, with cozy rooms spread across several floors. The top floor features a rooftop solarium offering stunning views—perfect for enjoying the complimentary continental breakfast and daily happy hour.
Beautiful Homes
Since my visit coincided with the History Festival, I arrive ready to see Charleston’s finest private homes and gardens. My choice is the Broad Street tour, a candy store of one Revolutionary-era home after another. We visit a beautifully restored house now owned by a writer offers a spectacular wall of windows overlooking a lush Southern garden. Then we tour a lovely old house restored with its high ceilings and hardwood floors and rear door opening to a delightful courtyard.
My day wraps up late afternoon, giving me time to explore King Street, Charleston’s oldest and most famous thoroughfare. This is the place to browse colorful historic buildings housing assorted restaurants, shops, and boutiques. The historic Francis Marion Hotel and the luxurious Charleston Place hotel are also located here.
The weather is balmy and the evening is young, so I cap off my day with a horse-drawn carriage ride through some of Charleston’s most beautiful neighborhoods. The ride offers glimpses of old churches, cemeteries, and The Battery, a historic seawall and promenade that’s one of the city’s most popular spots.
More History
The next day I set my sights on Rainbow Row, 13 Georgian homes built in the 1700s lining East Bay Street. Originally, these homes housed merchants who ran their businesses on the ground floor while living on the upper floors. After the Civil War, the neighborhood fell into disrepair until a Charleston couple purchased several houses and painted them pastel colors, sparking a transformation into the iconic rainbow street we see today.
After visiting Rainbow Row, I have several options for the next stop: stay on East Bay Street for a detour to the waterfront to catch a glimpse of Fort Sumter, a small island that was the site of the first battle of the Civil War. Or head to the Heyward-Washington House, a handsomely restored mansion that tells the story of a wealthy Charleston businessman.
Yet another option is touring the Aiken-Rhett House, a once elegant mansion that has been preserved (not restored). Untouched for years, the house gives a fascinating glimpse into the past, with its rusty chandeliers, peeling wallpaper and overall faded grandeur.
Come late afternoon, I head to Charleston City Market, established in the 1790s and one of the oldest public markets in the U.S. This is the ideal time to stroll through the stalls, where you’ll find everything from handmade soaps to woven baskets. A popular dinner destination is the nearby Hyman’s Seafood, serving fresh seafood since the 1890s.
Hilton Head
After one more morning and one more walk through Charleston’s historic district—detouring down Tradd Street with its lovely, tree-lined sidewalks—I pick up my rental car for the roughly two-hour drive to Hilton Head Island. This paradise of white sand beaches lies just south of Charleston, and was once home to dozens of plantations before evolving into a mix of private communities offering accommodations, recreation, and shopping.
On the Beach
I check into the Hilton Beachfront Resort and Spa, a light and airy hotel with direct access to the beach. Other coastal hotels include the Omni Hilton Head Oceanfront Resort and the Hilton Head Marriott Resort and Spa. After a long day of exploring and driving, I unwind by taking in the beautiful sunset from a chair near the water.
Venturing Out
The next day starts with a leisure morning followed by a stroll along the coastal trails of Hilton Head. Golf is always a popular activity here and there are famed courses to choose from. I am driving to Bluffton, a beautifully preserved Lowcountry town on the banks of the May River. Bluffton is home to the largest collection of antebellum buildings in the South. A walk through Old Town reveals structures dating back to pre-Civil War times. The downtown is charming but now sports a mix of old and new cafes, boutiques and restaurants. For a taste of local culture, make a short trek out of the downtown to The Bluffton Oyster Company, South Carolina’s last hand-shucking house, where you can sample May River oysters, clams, and mussels.
With its waterfront location, Bluffton is a popular destination for maritime activities, and during the summer months, the town’s only boat launch becomes a gathering spot for boaters.
If Time Permits
The drive back to Hilton Head is a short one. If you have time en route, consider a visit to Harbour Town in Sea Pines Plantation. The entrance fee gives you access to the shopping area, restaurants, and historic sights, including the Sea Pines Forest Preserve, home to ancient shell rings from the native tribes that once inhabited the island.
One More Jewel
I have one more oceanfront night in Hilton Head before heading back to Charleston. On the drive back I make a detour to Beaufort, the Civil War-era town set on the Beaufort River. First discovered in 1514, Beaufort has row after row of streets lined with beautifully restored mansions and moss-draped oaks.
Beaufort is also home to a wealthy neighborhood known as The Point, where antebellum mansions like the Fripp House (featured in The Big Chill and The Great Santini) stand as reminders of the area’s rich history. Enjoy a relaxed walk through the neighborhood before heading downtown to browse antique shops and enjoy a meal at one of the local cafes. If this is your final stop, linger. It’s just a short drive from here to the Charleston airport for your return trip home.
-Rose