Hilton Head Island Day Trip: A Day in Charleston, South Carolina

Less than two hours north of Hilton Head Island, Charleston is a must-do day trip full of Southern charm.

Before my husband and I had kids, we decided to move from our Midwestern abode and try something new. We chose Charleston, South Carolina, where I’d spent a summer interning in college, and we grew to love the area’s historic homes, hanging moss and coastal location.

Eight years later, I’m a Charleston expert. And while it’s hard to fully experience the city in a day, I’ll show you some of most celebrated — and off-the-beaten-path — things to do on a day trip from Hilton Head Island.

Experience the Living History

Charleston is as close as it gets to stepping into the antebellum South. Set within Charleston Harbour is Fort Sumter, where the Civil War began. Visitors can tour the fort by taking a boat to the island, which is visible from downtown Charleston. During the city’s hot summer months, head out as early as possible to avoid the noonday sun.

Locals have bought and sold goods at the historic City Market since the late 1700s, including a rage of fresh veggies, shrimp and fish, and, of course, the city’s famed sweetgrass baskets. These baskets can go for a pretty penny, but don’t be intimidated by the ladies weaving them as they sit at their stalls; they do negotiate!

If you want that full southern plantation experience, the Charleston area offers several options. Boone Hall Plantation is one of my favorites — its Avenue of Oaks is picture-perfect. Drayton Hall is one of the few plantations where the original home still stands, dating back to 1738.

For lovers of all things floral, don’t miss the lovely Magnolia Plantation and Gardens or Middleton Place. Both estates feature grandly manicured gardens along the Ashley River, a scenic waterway with diverse wildlife.

Quick Tip:

Simple strolling through the historic downtown is one of the best ways to see Charleston. Along the way, you can admire the architecture, historic features like old hitching posts, and gorgeous gardens glimpsed through wrought iron gates.

Enjoy a Stroll in this City on the Water

Set between the Wando and Ashley Rivers, historic downtown Charleston is literally surrounded by water. One of my favorite weekend or evening activities — perfect to do on a day trip — is a walk along the Battery downtown. My husband and I look out into the harbor and let our kids search for dolphins and toss rocks into the sea.

As we walk along the Battery, we also enjoy admiring the colorfully-painted homes that make up Rainbow Row, taking a dip in the city’s famous Pineapple Fountain (which my kids can never resist on a hot Charleston day!), and sitting on the leisurely swing in Waterfront Park.

Take a Trip to the Beach

Within just 30 minutes of the city are multiple islands with beaches, each with its own personality, and filled largely with locals instead of tourists. On the north side of Charleston, my family enjoys the elegant Isle of Palms and Sullivan’s Island. Both are authentic beach communities where beautiful pastel-colored beach homes fill the shoreline.

Charleston’s southern side is home to Folly Beach, which has a funkier and younger feel; the natural John’s Island; and the getaway of the wealthy, Kiawah Island. To really feel like a local, I recommend exploring two secret spots. The old Sullivan’s Island bridge once connected the mainland to the island, but it’s now a charming pedestrian walkway. Meanwhile, the Morris Island Lighthouse is a slice of fascinating local history: It’s the site of a battle led by the 54th Massachusetts Infantry, a black regiment, the story of which was told in the movie “Glory” with Denzel Washington. Today the lighthouse eerily stands alone and surrounded by the sea.

Quick Tip:

Spring is one of the best times to visit Charleston, as the vibrantly-hued azaleas begin to bloom. These southern flowers grow not only in gardens, but in lushly wild proportions by the side of the road as well!

Feast in South Carolina’s Culinary Capital

During our time in Charleston, the area has transformed from a fairly small town to a much more vibrant metropolis. The food scene, which was always fabulous, has also grown in the past decade; many restaurants and chefs have rightly gained national acclaim.

The lovely Circa 1886 is an upscale eatery set in the former mansion of a wealthy Charlestonian. It’s the ideal dinner spot for anniversaries and celebrations. For mouth-watering French food, don’t miss 39 Rue de Jean — the fluffy quiches pomme frites are the best around — and 82 Queen, which is set in a charming old home. To visit a local hangout, plan your Charleston day trip around lunch at The Mustard Seed in Mount Pleasant, which is just across the Wando River.

While you could easily spend a week in Charleston, it’s certainly worth a day trip, as well. Explore the history, spend time along the water and grab a delicious lunch and dinner filled with the fresh seafood before making your way back to Hilton Head Island for unparalleled golfing, adventure and relaxation.

Quick Tips:

The Charleston Food + Wine Festival, held each February and March, is a great way to sample the city’s outstanding food scene.


Where to Stay:

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