The 13th-century walls that once defended Montalcino from invaders also hid it (it might be assumed) from travelers as well. It wasn’t until a few decades ago—when Brunello, the town’s signature wine, hit the market—that Montalcino began raking in visitors. Today, it’s a mecca for red wine lovers, who come to sip and dine at its scenic wine estates (Castello Banfi, Le Potazzine, and Poggio Antico are three favorites for their pairing menus and outdoor restaurants.) Another advantage to flying off the radar for this long? The resident 14th-century castle, sequestered among the region’s olive groves, is almost perfectly preserved. After a tour, bed down at the restored Castello di Velona, whose thermal spa and pool overlook the Val d’Orcia.