The Holy Land guidebook created by the Franciscan Niccolò da Poggibonsi during his four-year journey in Syria, Palestine, and Egypt (1346–50) has only been known through unillustrated manuscript copies of the fifteenth and sixteenth centuries. The woodcut illustrations of the printed version of the guidebook, published anonymously in Bologna in 1500 and reprinted over sixty times until the nineteenth century, have been dismissed as works of artistic fantasy. My project focuses on four previously unknown illustrated manuscript copies which were the basis of these woodcuts. These illustrate every major building and city of the Holy Land—including the Holy Sepulcher, the Dome of the Rock, and the cities of Damascus and Cairo. The oldest version could be the autograph copy, with drawings created by Niccolò da Poggibonsi himself. More generally, the manuscripts provide evidence for how the visualization of Holy Land architecture in Italy emerged from the textual culture of pilgrimage accounts.