This study investigates the representation of Saracens in Boiardo's Inamoramento de Orlando and Ariosto's Orlando furioso, a subject that has attracted growing scholarly interest in recent years. Chapter I assesses the degree of realism in Boiardo's and Ariosto's portrayal of Islam and Islamic culture and locates the two poems in their historical context. Bringing to light unpublished archival material and other little-known historical sources, I argue that Boiardo and Ariosto drew inspiration from contemporary courtly culture which was characterised by openness towards the figure of the foreign prince. Chapter II explores Boiardo's engagement with earlier chivalric literature. It examines Boiardo's use of names and characters from earlier texts and evaluates the Saracens' contribution to the ideology that underpins the poem. It is shown that Saracens play an important role in promoting the ‘Arthurian’ chivalric ideals. Chapters III and IV analyse Ariosto's indebtedness to and departures from his predecessor, suggesting that there is a much greater continuity between the two Orlandos than is allowed by Cavallo and other scholars who are anxious to stress Ariosto's 'conservatism'. While chapter III is devoted to a wide-ranging analysis of the Saracen world in Ariosto, chapter IV deals with a topic that has recently generated much heated debate, namely the climactic confrontation between Rodomonte and Ruggiero and the ending of the Orlando furioso and how it should be understood, and I propose a new interpretation of the final canto by highlighting the concept of honour, a fundamental value for both Boiardo and Ariosto as well as for their early readers and for many chivalric authors alike. In my view, Rodomonte is the true winner of the duel. The significance of his 'moral' victory is examined in the study's final conclusion, where it is argued that it undermines Ariosto’s encomiastic project.