This paper analyzes travel narratives in Arabic between Iberia and North Africa in the sixteenth and seventeenth centuries to analyze the shifting Mediterranean frontier, cohering around watershed moments for the Muslim and Morisco communities in Iberia: 1492 and 1609-14. I argue that shifting boundaries are reflected in these travelers’ identities that can be seen as both/and constructs. As case studies, I analyze biographies and travel narratives by Leo Aricanus/Hasan al-Wazzan (d. ca. 1550), Ahmad ibn Qāsim al-Hajarī/Diego Bejarano (d. ca. 1640), and Mohammed al-Wazīr al-Ghassanī (d. 1707), who represent the Morisco community at different stages of their history. Leo/Hasan was born during a period of uncertainty for the Muslims of Granada, and although not a Morisco per se (a proto-Morisco, I would argue), his family left Granada for Fez circa 1490; Ahmad/Diego was a Morisco who witnessed the events of the Inquisition and eventually fled to the Maghrib in 1598; and al-Ghassanī was a descendant of Morisco exiles in the Maghrib and was the first documented Arab and Muslim traveler to Iberia after the expulsion of the Moriscos. These watershed moments are documented by these travelers whose identities are products of the turmoil in the Mediterranean. The different ways in which they negotiate their identities and grapple with their circumstances and hybrid identities enable us to understand the Mediterranean as a site of diplomacy, fluidity, and exchanges, rather than mutual hostility. Leo/Hasan describes himself as a “wily bird” called Amphibia who has the ability to swim with the fish and fly with the birds. He writes of his experience between cultures and languages, where he identifies himself with what is most convenient for the situation, choosing when to present himself as Granadan or African. Ahmad/Diego similarly grappled with a double identity and served as a translator between Arabic and Castilian, which made him a cultural mediator. Al-Ghassanī, a century later, narrates an Arabo-Islamic memory of Christian Spain as he travels through its different monuments and landscapes, also conjuring a maurophilic memory of Islam in Spanish Golden Age literature. I argue that these narratives are a radical reminder that behind the veil of otherness lies similarity, established by the hybrid identity and the persistence of its memory. The Mediterranean Sea, in these narratives, is transformed from a border to a connecting vessel that facilitates continuities between north and south and challenges binary oppositions that distinguish “Europe” from the “Islamic world.”