In early-sixteenth-century Tuscany, the small countryside convent of San Vivaldo was transformed into a new Jerusalem. A large number of chapels, decorated with sculptures, frescoes and reliefs, were erected under the supervision of the Franciscan order and in accordance with the Holy City’s topography. This thesis primarily examines the visual means by which the illusion of Jerusalem was constructed and what version of the Holy City that was offered to the San Vivaldo pilgrims. This is done through an analysis of the Chapel of the Holy Sepulchre and the Chapel of Calvary. In addition, possible connections between Franciscan meditation texts and the chapel complex’s art and architecture are explored. The scientific perspectives used are theories on visual culture as a vehicle for creating inner images; substitution; the interplay between memory, meditation and space; and pilgrimage as a liminoid experience. The results show that the San Vivaldo Franciscans strived to place the beholders in the depicted biblical stories by multimedial, affect-stimulating and interactive means. This strategy can be linked to the order’s meditation techniques, which also sought to bring the Christocentric narratives to life. In addition, the idiosyncratic shapes of the Jerusalem tomb and other significant architectural elements were recreated, which may have relocated the visitors mentally to the Holy City and, by extension, the proximity of Jesus. The Jerusalem that was built in San Vivaldo was neither one-sidedly biblical nor early modern. Instead, the site’s visual culture created several temporal and spatial layers that acted simultaneously and side by side.