Start with the Old Town – the highlight of the city where its more than 8,000-year old history started. Visit a few of the old houses turned into museums – the Ethnographic Museum and the Renaissance Exhibition of the Regional History Museum have the most extensive collections of historical items, retro-styled rooms, and explanation of what life used to be here two centuries ago. Balabanov House often hosts concerts and literature readings, while the Gallery of Zlatyu Boyadzhiev will introduce you to one of the most iconic Bulgarian painters.
Stop for lunch at the restaurant with one of the best views in Plovdiv, Philippolis. It is actually part of a complex with a private museum, art gallery, and art shop.
Explore the pedestrian Knyaz Alexander I Street, one of the longest walking streets in Bulgaria. Take a look at the Dzhumaya Mosque and find a refuge from the heat in the tiny park behind it, where you can see the names of famous Bulgarian authors written on the ground. Right next to the mosque, one level below, you can visit the remains of the Roman stadium where sports events took place. There is a hall where you can watch a short 3D animated movie about the history of the stadium.
Save the evening for one of the more recently renovated attractions favored by the residents of Plovdiv, the Singing Fountains. In the summer after dark, the fountain splashes playfully while you listen to retro Bulgarian songs, classical music, and famous tango melodies. The colorful lights shimmer, following the rhythm and creating that feeling for the dancing waters. The show takes place a few days a week, but as the dates vary, it’s better to ask for information at the local Tourist Information Center (+359 32 656 794; +359 32 620 229).
The fountains are off before midnight, so you can go to the Kapana district (between the mosque and the Maritsa River) to check the best craft beers and wine selections in town.
Get back to Kapana for your morning coffee, or drop by the nearby Dzhumaya Turkish Coffee and Pastry Shop (it is basically housed in part of the Dzhumaya Mosque). Indulge in some people-watching as Plovdiv dwellers normally do, especially on weekends. You can check the main pedestrian Knyaz Alexander I Street for shopping opportunities, from clothes (mainly local brands but a few international brands stores are available as well) to souvenirs.
A 10-minute walk from the pedestrian zone, the impressive Ancient Theater towers with its ancient columns (some of them restored, others recreated). It is located right over a traffic tunnel and you can see the cars passing below. The theater was used for theater performances and gladiator fights, and it is still in use today, hosting a number of opera performances and concerts under the stars in the summer.
Plovdiv is located on and around several hills, and the best sunset spots are on top one of them. The easiest to access is the point on top of the Old Town (where the Puldin Fortress used to be, though nothing but a few stones remain today) where friends and couples gather to watch the sun setting over the buildings and the river. Make sure you camera’s battery is charged, as you may want to take advantage of the perfect photo opportunities.