Nestled in a dip amidst Macedonia’s sun-scorched southern mountains, Prilep marks the beginning of the Pelagonian Plain. A dash of red-tiled roofs encased in a buffer zone of tobacco plantations, the town is primarily an industrial hub that bears the recognisable names of some of the world’s biggest cigarette brands. However, there’s also a taste of both history and the new age Macedonia here, with the crumbling remnants of the great Markovi Kuli Fortress crowning the hillsides above town and one shiny new central square that bustles with local chatter right throughout the summer. The town’s Clock tower leads travellers to the orthogonal streets of the Old Bazaar, where its incumbent food joints serve up gritty Greek coffees and paprika-flavoured shirdan on the menus. A little off the city centre, the Archangel Michael Monastery rises out of the rocks, where Prilep tour guides showcase amongst other monuments, the famous St Nikola Church, a masterpiece from the middle ages. A couple of Byzantine monasteries – Treskavec and Zrze – also crown the limestone ridges around the city, worth a trip for their medieval frescos and dramatic perches atop bluffs and cliffs.