Around the middle of the sixteenth century, Japan's temples and shrines began producing pilgrimage mandalas (sankei mandara), paintings whose primary purpose was to encourage travel and contributions to sacred sites. These are pictorial maps, schematic visual travel guides that depict specific sites and outline the roads, bridges, and landscapes leading to them, as well as each site's origin history (engi), the sacred rituals in that place, and the pleasures to be enjoyed in the surrounding area. However, this article reveals that, rather than being objective guides and road maps, sankei mandara are highly constructed, manipulated images, imbued with both a numinous view of the landscape and partisan views of the represented site. This article discusses how these seemingly incongruent features coexist and intertwine in sankei mandara and by what art and artifice painters have achieved these effects. The author analyzes the multiple layers of sankei mandara and considers how each of the layers works to achieve particular ends, whether to express an aspirational world view, diminish an institutional rival, or bolster the position of the commissioning patron. Reading sankei mandara in this way enriches our understanding of the nature of maps in general, while also allowing access to a particular moment in Japan's social, religious, and institutional history, providing insight into a range of historical issues left murky when examined using textual analysis alone.