This thesis reveals a culturally sophisticated Cypriot elite that moved with ease between Cyprus and Venice, between Orthodox and Latin devotions, between icon painting and up-to-date Italian artworks. Arranged in the form of microhistories, the present work discusses how the insular nobles negotiated their identity between the two centres during the early modern period. In Renaissance Venice, where they strove to be associated with the upper echelons of patrician society, the Cypriot elite followed the latest metropolitan trends, while on the island, where they were subject to a different set of social pressures, they opted for works in the traditional Byzantine style. At the heart of this study are three noble Cypriot lineages - the Podocataro, Costanzo, and Synglitico - that were well established in both Cyprus and the lagoon. Contrary to the prevailing perception of Cyprus as a distant colony where Renaissance culture found faint echoes only in the major urban centres, these families engineered and exploited opportunities for economic and social advancement that the shared political space of the stato da mar afforded them. Through the recovery of previously overlooked archival documents, the business and the domestic worlds of the three Cypriot families is reconstructed, while these sources shed new light on a series of significant paintings by leading Venetian masters.