The main topic of this study is the travel narrative’s illustrations of the Castilian Jeronymite friar Diego de Ocaña. In 1599, the monk was sent by his superiors to colonial Spanish America to collect alms for the major shrine of Saint Mary of Guadalupe, in Extremadura, Spain. Ocaña traveled to Puerto Rico, Cartagena, Portobelo, Panama, throughout the land of the Viceroyalty of Peru, including territories of today’s Chile, Argentina and Paraguay, with longer and more mission-productive sojourns at Lima, Potosi and Sucre. Ocaña wrote and illustrated an account of his journeys that covers his adventures from 1599 to 1605. The extant manuscript is a pluri-generic text, since it is framed and structured as a travel narrative, yet it contains drawings, maps, a partial autobiography, his dramatic work entitled Comedia de N. S. de Guadalupe y sus milagros, some poetry authored by him and others, the accounts of the baroque celebrations in honor of Saint Mary of Guadalupe, and the detailed description of the image he painted at Sucre. This dissertation examines the drawings and maps of the manuscript in conjunction with Ocaña’s travel narrative and descriptions of the New World, against the backdrop of the colonial Spanish American cultural and sociopolitical context at the end of the XVI and the beginning of the XVII centuries. The theoretical perspective of this dissertation follows mainly Edwin Panofsky’s method for iconographic study, who proposes that images could be studied on three levels: a pre-iconographical description, an iconographical analysis, and an iconographical synthesis. Ocaña’s illustrations offer a fascinating window into his personal views of the New World and those of his contemporaries. I viewed them in fact as social signs or cultural constructs that were shaped by the context surrounding the monk. Since most of the illustrations are representations of indigenous peoples, these drawings allow an understanding of the process in the creation of a Spanish American identity and uncover among other relevant ideas Ocaña’s admiration for the Araucanian warriors and the stereotype of Indigenous women as sexually aggressive temptresses.