Charleston may be a small town, but this city punches well above its weight. When you consider everything it has to offer—history, culture, food, charm—it’s no wonder the so-called Holy City has topped our list of the best small cities in the U.S. for nine years running. While its robust F&B scene, which includes a steady annual circuit of nationally recognized food and culture festivals, continues to be a draw, visitors are rarely prepared for the city’s good looks. Stately homes, cobblestone streets, waterfront views, and an abundance of flowering window boxes only add to its welcoming vibe. Find a seat among its many outdoor terraces for a drink, and some fresh oysters (we recommend hitting The Ordinary) and try to resist the urge to up and move here.