Despite their increasingly updated and expanded content, maps of the Balkan Peninsula in the Renaissance largely iterated the frame and format of an older, almost archetypal regional map, Ptolemy’s tabula nona Europae. An agreed rationale behind Ptolemy’s dominance is the collapse of antiquity into modernity through which humanists were able to establish the ancient cartographer as both a classical authority and a model for scientific renewal. Yet a closer look at these maps reveals a more complex history than the one suggested by univocal accounts of the origin of modern cartography. On the one hand, it helps relocate the Balkan Peninsula at the crossroads rather than at the periphery of the routes through which cartographic knowledge was transferred, circulated, and developed between East and West. On the other hand, it multiplies the range of places, actors, and motives involved in cartographic initiatives whose claim to modernity set them apart from other forms of mapmaking steeped in nautical and military practices. In this view, the philological quest which at the end of the thirteenth century led Byzantine scholar Maximos Planudes to rediscover Ptolemy’s work would a century later give way to the political hopes of Manuel Chrysoloras and the ethical ambitions of Coluccio Salutati. Later, this legacy would be intercepted by the diplomatic and poetic goals of Francesco Berlinghieri, the search for empirical validation of Pietro Coppo, and the educational mission of Johannes Honter. All these encounters draw a compelling history of cartographic modernities that projected disparate motives, visions, and techniques on the geographical slate of the same region. Despite their common Ptolemaic cover, these maps ultimately escape the logic of a single narrative, diffracting and recomposing the highly articulated geographical space of a region that lay at the juncture between land and sea, Christianity and Islam, war and trade.