The Relación of Antonio de Montezinos (1644) recounts one of the few direct encounters between a Jew and the New World during the formative period of European expansion and colonization of the Americas. Montezinos’s narrative of his encounter with the lost tribe of Reuben in the Northern Andes is of obvious relevance to the history of early modern messianisms as well as the proto-anthropological question of the origin of the Native Americans. However, in this essay I look at the Relación as a uniquely Jewish American narrative of spiritual transformation; Montezinos’s experience in the Americas inspires a radical reassessment of his life and religious commitments. This transformation is fueled by the journeys he embarks upon and the texts—both oral and written—which he encounters along the way; both text and travel dialectically inform his process of self-discovery. By focusing on this one angle we can see how Montezinos’s Relación participates in the wider discourse of the European encounter with the Americas, and how, at the same time, it is integral to Jewish literature, to the writings of individual Jews as they attempt to make sense of the New World.