Plovdiv’s Old Town is one of the oldest continuously inhabited cities in Europe, with evidence of settlement stretching back over 8,000 years. Spread across three of the city’s original seven hills, the cobblestone district is an open-air museum of layered history — Roman amphitheaters, Ottoman mosques, Bulgarian Revival mansions, and contemporary art galleries all coexist within a few hundred meters. The centerpiece is the magnificently preserved 2nd-century Roman Amphitheatre, still used for live performances today and offering sweeping views across the Thracian Plain.

The steep, cobbled streets are lined with colorful 19th-century National Revival period houses, their upper floors jutting out over the narrow lanes in a distinctive style unique to this region. Many have been converted into museums, galleries, and atmospheric restaurants. The Ethnographic Museum, housed in the stunning Kuyumdzhioglu House, and the Philippopolis Art Gallery are particular highlights.

Pro tip: Start your exploration at the Roman Amphitheatre and work your way uphill through the quieter residential streets to the Nebet Tepe hilltop, where the oldest settlement remains in Plovdiv offer panoramic views and a wonderfully peaceful escape from the busier lower streets. In the evening, head to Kapana, the creative district just below the Old Town, for craft cocktails and live music in converted workshops.