Chess in the park, Plovdiv. Photo: Photo Beto / iStock.
For many of our readers, Bulgaria has rarely ranked high on the list. Plenty have traveled through Greece and Turkey on either side without ever crossing the border.
Time Out disagrees. The city-guide publisher, whose earlier picks included Albania and Montenegro, put Plovdiv, Bulgaria's second-largest city, first on its 2026 list of Europe's most underrated destinations and called it Europe's most underrated city. Writing for International Living magazine, Mary Charlebois and Kevin Scanlon said that a sunny Sunday on Plovdiv's main pedestrian street felt like Paris 30 years ago, with couples and families at sidewalk cafés over coffee and pastry.
Plovdiv is about two hours southeast of the capital, Sofia, and most visitors notice the unhurried pace right away. Locals have a word for it: aylyak.
The word comes from the Turkish aylak, meaning idle, but in Plovdiv it means taking your time and enjoying it. A morning coffee can turn into a long lunch with wine.
The main street
Plovdiv's main pedestrian route runs a little over a mile (about 1.75 kilometers), from Central Square to the footbridge over the Maritsa River. On warm evenings, it fills with people walking, shopping, and sitting outside at cafés. The pastry on the tables is banitsa, flaky layers of filo filled with cheese, sold by the slice from small bakeries.
Near the north end, you'll come to the curved marble seats of a Roman stadium built under the emperor Hadrian. It held up to 30,000 spectators, and most of it still lies beneath the shops. We like that it isn't set apart from daily life. People walk past it on their way to coffee.
The Old Town
Uphill from the main street is the Old Town, with cobbled lanes lined with 19th-century merchants' houses painted in bright colors. Many are now small museums and galleries that charge a few euros. Kuyumdzhioglu House holds the city's Ethnographic Museum, and its garden is a good place to sit.
At the edge of the hill is a Roman theatre, one of the best-preserved anywhere, that still hosts open-air concerts. Check the schedule before you go.
Goldsmith Street
Below the Old Town is Kapana, a few blocks of narrow lanes where craftsmen worked for five centuries. The street signs still say what was made there: Goldsmith Street, Furrier Street. Today small workshops sell leather goods, jewelry, and ceramics, often made by the person behind the counter.
In the evening, Kapana is where the city goes out, and it's where aylyak is easiest to understand, since nobody seems in a hurry to clear your table.
The cellar in Brestovitsa
Wineries surround Plovdiv, and the local red grape is Mavrud. Order it. In 2025, a European Best Destinations poll named Plovdiv Europe's best wine capital.
About 11 miles (18 kilometers) southwest, the village of Brestovitsa has one of Bulgaria's densest clusters of wineries. Bendida, a family winery there, made its first wine in 1936. Production stopped after the communist takeover in 1944, and the founder's grandson later rebuilt the cellar. He now makes the wine with his daughter, Elizabet Porteva. Book tastings ahead, especially in autumn during the harvest.
Finding your way
Bulgarian uses the Cyrillic alphabet, so street signs can be a puzzle outside the center. Menus in town often come in English, and younger people usually speak it. A translation app handles the rest.
One thing to know on your first day: traditionally, Bulgarians nod to mean "no" and shake their heads to mean "yes." Shop and restaurant staff often switch to the international gestures with visitors, but it can still catch you off guard.
Plovdiv has a reputation as one of Bulgaria's easiest, most relaxed cities, including for women traveling alone.
Getting there
Bulgaria is part of Schengen, Europe's passport-free travel area, so you won't face routine border checks arriving overland from Greece, though coming from Turkey you still cross a border. The country adopted the euro in January 2026, and buses from Sofia take a bit over two hours.
Give it three or four nights, with a day for the wine country and another for Bachkovo Monastery, about 18 miles (30 kilometers) south in the foothills of the Rhodope Mountains. If you are already going to Istanbul, Plovdiv is about seven hours away by direct bus, or overnight by sleeper train.
