Italian adventurer and raconteur Ludovico di Varthema (d. 1517) is best known for visiting Mecca and traveling throughout South Asia—and for his fluid identity, which included posing as a Muslim, that facilitated his journeys. But his Itinerario also holds a fascinating and understudied account of late Mamluk Damascus, where he stayed “some months in order to learn the Moorish language” (Arabic). The city captured Varthema’s imagination and set a path for the rest of his travels. In his account, he details Damascus’s economy, natural environment, and Christian identity. He also comments at length on the city’s oppressive military government and soldiers’ abuse of local women. In doing so, Varthema mixes genuine insight with naïve prejudice (and gilded artifice) on a variety of topics, including how Mamluk commanders gain and lose their offices, the military value of the citadel, the plural legal system, and the prostitution scene. While overtly critical of his Mamluk hosts, Varthema, himself a Renaissance man-at-arms, was drawn to the Mamluk way of life and the privileges—material and sexual—it afforded. Moreover, he held all Mamluks to be “renegade Christians,” another layer of identity that resonated with his own. This paper will analyze Varthema’s description of Damascus, parsing fact from fiction with the help of contemporary Arabic sources (e.g., Ibn Tawq and Ibn Tulun). It also will examine Varthema’s textual bid for authority with his home audience—the Italian travelogue was first printed in Rome in 1510, and then briskly translated into other European languages. For context, the paper will engage current scholarship on religious pilgrimage, Orientalism, Mediterranean hybridity, and a putative shift from late medieval to early modern world travel. Some have seen in Varthema’s work a shift toward secular and empirical reportage—a new literary genre by the “curious” traveler. Others maintain that in denouncing Islam, searching for Christian converts and allies, and fighting with distinction for the Portuguese, the Italian, in the end, was not so radical. This was medieval travel and crusade repurposed for the 16th Century.