In the sixteenth century, the Spanish Crown moved to compile a comprehensive knowledge of its European and American landholdings to materialize the idea of a unified and civilized empire. Peninsular officials sent questionnaires to the Americas, including a request for “paintings” of the urban and natural landscape, without much detail on the project’s guidelines. The varied responses sent back to Spain are known as the Relaciones Geográficas de Indias. This essay investigates the cultural negotiations and potential for Indigenous representations of “depth of place” embedded in one such painting from the Peruvian highland region of Yauyos and Huarochirí. By analyzing colonial-period sources and using spatial modeling, this research underscores the different portrayals of space coexisting on the map. By comparing the painting with contemporary colonial sources, this article examines ongoing negotiations of natural and urban landscapes and an emerging view that synthesized different readings of the same landscape in a period of colonial dislocation and reinvention.