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This paper analyzes Venetian involvement in Latin Christian pilgrimage to Palestine in the final decades of the Mamluk Sultanate (c. 1480–1517). It draws upon pilgrim narratives by Venetians, other Italians, and transalpine authors, as well as Venetian legislation concerned with the transportation of pilgrims to the Holy Land held at the Archivio di Stato di Venezia (ASVe), in particular the Ufficiali al Cattaver and Senato, Deliberazioni Mar. What follows is a survey of various Christian-Muslim material exchanges involved in pilgrimage in the late fifteenth and early sixteenth centuries, together with the most salient problems arising from those transactions. The article argues for the importance of cross-cultural material exchanges in facilitating interactions between Muslim authorities and Christian travelers in the eastern Mediterranean at the turn of the sixteenth century. Having highlighted the main challenges and concerns faced by these interlinked groups, it finds evidence of extortion and exploitation perpetrated upon the pilgrims by Venetians and Mamluks alike, but at the same time it also considers a few of the means by which the travelers could evade conflict and continue on their journeys.