You wouldn’t expect a place so steeped in history to be so hip, but Charleston’s full of surprises. On the surface, this well-heeled city is the epitome of southern charm. Warmth and hospitality are practically baked into the well-manicured streets. But once you get to know your way around, an unexpected and trendy hotspot emerges, bustling with fashion, nightlife, gourmet food and plenty of Southern grace. After all, no one said that historical had to mean stuffy. And the longer you stay, the easier it is to be seduced by this city.

Exploring Charleston’s historic sites is one of the best ways to appreciate the city’s deep Southern roots. And if your U.S. history is a bit foggy, here’s a refresher: Fort Sumter wrote Charleston into the history books when it became the place where the first shots of the American Civil War were fired. A quick boat journey will deliver you to the Fort Sumter National Monument, where you can spend an afternoon exploring the original ammunitions and fortifications from this momentous time in history.

If historic dwellings are more your speed, Charleston doesn’t disappoint. The city’s historic district is punctuated with plenty of antebellum architecture, perfect for an afternoon of pretending to be an elite 19th century socialite. The Nathaniel Russell House is particularly stunning, featuring a breathtaking spiral staircase and a drawing room lined with 1,000 sheets of 24k gold leaf. If you’re looking for more sights, grab your camera and head to lower East Bay Street for a stroll and a photo op alongside the candy-colored homes lining Rainbow Row. There’s a reason it’s one of the most photographed spots in the city.

When the sun sets, nearly everyone retreats immediately to their favorite rooftop bar. This unique Charleston tradition also comes with a sweet reward—stunning views of the historic cityscape. You shouldn’t have trouble finding one (they’re literally everywhere) but just in case, here’s a few recommendations. The Vendue Hotel offers a tasteful and artful atmosphere, handcrafted cocktails, and soaring views of the French Quarter and the Charleston harbor. If you want to add a dash of funk to your nighttime hangout, head to Élevé, located on the rooftop of the Grand Bohemian Hotel. With its deep wine list, specialty cocktails, and décor that looks like it was curated from the Mad Hatter’s private collection, your night will take on an eclectic and stylish vibe. And if you have a large group in tow, check out Stars on King Street. They’re famous for their frozen Bellinis and being the only place in the city to boast a full 360-degree view of the historic district.