Since its designation as the capital of the great Macedonian empire, bearing the name of its tragically ambitious ruler, Alexandria was regarded as a multicultural node. Located on the delta of the Nile River, in the southeast shore of the Mediterranean Sea, Alexandria was on the very crossroad of various global trade routes, home to markets of luxury goods and exotic spices, but also of manuscripts and books in various languages. Indeed, narratives that go back to antiquity celebrate the city’s cosmopolitan quality, envisioning that its temperate climate of pleasant habitability attracted both merchants and thinkers from the four corners of the earth. In the late Middle Ages, furthermore, this was not merely a metaphor reflecting imperial aspirations, but a reality; the city, under the firm rule of the Mamluk regime, came to house a number of exceptionally vibrant communities. Christians (Copts, Venetians, and Pizans) and Jews of various backgrounds shared an urban space with their Muslim neighbors and rulers. In recent years, in fact, Alexandria has been the subject of a number of studies that sought to reflect on the nature of the relations between its non-Muslim inhabitants and the Muslim regime. These studies, however, based primarily on a legal source-base and conceptual framework, share an implicit conviction that trade functioned as the sole principle which both regulated, and made possible, contact between various communities that, on the face of it, nurtured opposing, at times competing, worldviews. This paper, in contrast, turns to works in verse and prose, in Arabic and Romance, in order to consider how the various groups in Alexandria came to conceptualize their mutual entanglement as well as their religious and political identities. It argues that authors came increasingly to map their cultural and literary stakes, as well as their claims for hierarchical power and sacral sovereignty, on articulations of multilingualism. They, furthermore, mapped these articulations on a Mediterranean space characterized by measures of interconnectivity and mobility. For authors in late medieval Alexandria the Mediterranean, as a zone of mutual intelligibility, increasingly emerged not only as a literary trope in works of fiction, but also as a hermeneutic strategy through which they conveyed claims about their own geographic, political, and literary traditions. This approach to the study of the interactions between the various groups in Alexandria may contribute to a collective attempt to revisit outdated conceptions regarding the attitude toward dhimmis in medieval Islamic societies.