This book explores how the medieval "Orient" — the non-Western and non-Christian world — was imagined in texts and images of travel, exile, and cultural encounter across the Mediterranean. Through readings of the Historia Apollonii regis Tyri, Aucassin et Nicolette, Floire et Blancheflor, Le Roman de Silence, La Manekine, Boccaccio’s works, and Chaucer’s Canterbury Tales, it traces the movement of stories, peoples, and identities across languages, religions, and geographies. At the center of the study is Boccaccio, whose works reveal the Mediterranean as a space of crossings, conflict, hybridity, and exchange. Particular attention is given to his De Maumeth propheta Saracenorum, published here for the first time in English, where Boccaccio approaches Islam and the life of Muhammad with a complexity rare for his time. Across these narratives, women such as Tharsia, Blancheflor, Biancifiore, Nicolette, Silence, Alatiel, Zinevra, and Manekine cross dress, travel, and trade stories across the sea, transforming displacement into survival and memory. The sea emerges as a living archive, revealing the enduring power of literature to preserve encounters, voices, and worlds across time and space.