Dubrovnik (Ragusa) and Livorno (Leghorn) are two old maritime cities in the Mediterranean whose strong cultural and scientific connections are here explored through the work of Vicko Dimitrije Volčić (Vincentius Demetrius Volcius Raguseus). Volčić worked in Livorno and Naples as a maker of portolan charts from 1592 to 1607. His twenty-eight charts known today represent a compendium of knowledge at a time in which intertwined practices and traditions of Dubrovnikʼs, Catalan, Neapolitan, Livornian, Genoese, and Venetian sailors reflected the cultural relations between the East and the West in general. This movement of charts and people through the means of trade, travel, and diplomatic activities formed the basis for cultural and knowledge exchange. Based on archival research of Volčićʼs charts as well as of charts by his contemporaries, this paper aims to identify knowledge exchange flows, cultural influences, and cartographic practices of individual masters and cartographic workshops that Volčić applied while working at the Livorno cartographic workshop.