Sofia Airport → Plovdiv

Plovdiv has been continuously inhabited for roughly 8,000 years, making it one of the oldest cities in Europe — older than Rome, Athens or Constantinople by most estimates — and that depth of history is visible in layers as you walk through it. A beautifully restored Old Town of colourful 19th-century Revival-era mansions sits directly above a working 2nd-century Roman Theatre that still hosts concerts today, with Thracian, Roman and Ottoman remains scattered throughout the wider city centre.

Bulgaria's second-largest city was named a European Capital of Culture in 2019, and the investment that came with it turned the once-industrial Kapana ('the trap') district into a dense, walkable quarter of independent galleries, coffee roasters, craft bars and design studios. Combined with a growing food scene and its compact, pedestrian-friendly centre, Plovdiv now rivals Sofia as Bulgaria's most rewarding city to simply wander.