This essay considers how the reencounter between Christians and Jews over the course of the sixteenth century shaped the evolution of European attitudes toward Jews. It notes that, while 1492 marked an end to a long-standing era of Christian-Jewish relations in Europe, it also signaled an important shift toward new thinking about the once-familiar Jews. The combined effects of the absence of Jewish communities from most of Western Europe, the failure of Christian society effectively to integrate the Conversos of Spain and Portugal, and the expanded cultural horizons engendered by the Age of Discovery helped challenge and alter popular images of the Jews that had been inherited from the Middle Ages. The lands of the Muslim Mediterranean operated as an important stage on which the Christian reencounter with Jews played out, and travelers’ accounts of the Jews in these lands came to exert a powerful influence on the way in which the image of the Jew was recast in the European imagination. The discussion here seeks to expand on recent work on sixteenth-century Christian ethnographies of the Jews and to complicate some of our notions of the nature and development of Christian attitudes toward the Jews during the transition from the medieval period to the early modern.