Charleston, SC: The South's Most Charming City

If you've never been to Charleston, South Carolina, I want you to picture this: a warm evening in April, the scent of jasmine drifting through streets lined with pastel-painted antebellum homes, the clinking of glasses at a rooftop bar overlooking the harbor, and a dinner that rivals anything you'd find in New York or San Francisco. That's Charleston — and it's one of the most consistently underrated luxury destinations in the entire country.

Jay and I have sent dozens of clients to Charleston over the years, and without exception, every single one comes back saying the same thing: "We had no idea it was that good." If you're looking for a long weekend that punches far above its weight class, Charleston is your answer.

The Neighborhoods Worth Exploring

Charleston's magic is concentrated in a walkable peninsula, and understanding the different neighborhoods makes all the difference in your experience. The Historic District is where most visitors start — and for good reason. The Battery promenade, Rainbow Row (those famous pastel facades along East Bay Street), and the antebellum mansions of South of Broad are genuinely jaw-dropping.

But the neighborhood Jay and I are most excited about right now is Upper King Street. This is Charleston's culinary and cocktail epicenter, with new restaurants, cocktail bars, and boutiques opening seemingly every month. If you want to eat and drink well — and you do — this is where you'll spend your evenings.

For a quieter, more residential feel, wander into Harleston Village or stroll along the French Quarter, where art galleries, hidden courtyards, and the St. Philip's Episcopal Church steeple dominate the skyline. And don't skip the Market District — the Old City Market has been operating since the 1790s and remains one of the great sensory experiences in American travel.

Where to Eat: A Serious Food City

Charleston has quietly become one of the best food cities in the American South — perhaps in the entire country. The culinary scene is rooted in Lowcountry tradition (think shrimp and grits, she-crab soup, and pimento cheese) but elevated by a generation of James Beard Award-winning chefs who've chosen Charleston as their canvas.

Where to Stay: Charleston's Finest Hotels

The hotel scene in Charleston has elevated dramatically over the past decade. Here are the properties we recommend to our clients most frequently, depending on their travel style.

The Dewberry is our top recommendation for the design-forward traveler. Set in a beautifully restored 1960s federal building, it has the feel of a private club — mid-century modern design, a spectacular rooftop bar, and a lobby bar (The Living Room) that's become a social institution. Walking distance to everything in the Historic District.

Zero George Street is what we recommend for couples seeking something more intimate. A collection of restored antebellum buildings around a courtyard, with just 18 rooms and suites. The evening cocktail hour, the exceptional breakfasts, and the genuinely warm service make it feel like staying at an elegant private home.

Belmond Charleston Place is the grande dame — the most traditional luxury choice, with a rooftop pool, full-service spa, and a central King Street location that can't be beaten. If you want the full service hotel experience, this is it.

Day Trips Worth Taking

One of Charleston's great advantages is its location. Within an easy drive are some of the most beautiful natural and historic sites on the East Coast.

When to Go

Charleston is a year-round destination, but timing makes a meaningful difference. Spring (March through May) is peak season for good reason — the azaleas are in bloom, the weather is perfect, and the city is alive. Book early if you're traveling in spring.

Fall (September through November) is our personal favorite time to visit. The heat of summer has broken, the crowds have thinned, and the light is golden in a way that makes every photograph look like a painting. October in Charleston is genuinely one of the great travel experiences in the American South.

Summer is hot, humid, and busy — but if that's when your schedule allows, Charleston handles summer well. The beaches are gorgeous, the restaurants are all fully staffed, and the energy is high. Just stay near the waterfront where the sea breeze helps.

Winter is the secret season. December through February brings cool but mild weather (average highs in the 50s°F), minimal crowds, and some of the best restaurant availability of the year. Holiday lights in the Historic District in December are genuinely magical.