Bulgaria’s ancient and romantic second city, Plovdiv is the 2019 European Capital of Culture for good reason. Ramble around the cobblestoned streets of the old town, have a peek at the 19th-century Bulgarian Revival–style mansions and climb at least one of its seven hills. The 200m-high Nebet Tepe (Prayer Hill) is particularly worth visiting for a stunning panoramic view; it also boasts the ruins of Eumolpias, a Thracian settlement dating from 5000 BC. Other highlights include the majestic Roman amphitheatre, built in the AD 2nd century under the reign of Emperor Trajan, and the Kapana artistic quarter, famous for its music and art festival that’s usually held in early June.
Getting there: Reaching Plovdiv takes just 90 minutes by car from Sofia (or even less due to the highway speed limit of 140 km/h). Buses and trains also run regularly; buses are more expensive but faster (it’s about two hours by bus and around three hours by train).