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Pastoralism, transhumance and the life of medieval shepherds remain a fascinating field of research, particularly in terms of socio-cultural, economic and environmental history. In contrast to the rich findings on pre-modern pastoralism in France, the seasonal herding practices and the socio-economic interaction of pastoralists with urban and rural societies in South-Eastern Europe remained largely unexplored. Hence, this article focuses on pastoralists in the medieval Balkans and the eastern Adriatic, particularly Venetian Dalmatia in the 15th century. After introductory reflections on Balkan pastoralism, the island of Korčula is examined as a case study in order to first elucidate the statutory and contractual basis on which local shepherds grazed their flocks on the island. Then the seasonal routine of the island’s shepherds is explored, including some of their socio-economic conflicts with the local rural and urban society, its communal administration and the Venetian governor of Korčula.