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This paper presents the results of research on the early career of the Jesuit painter Democrito Bernardo Bitti (b. 1548 in Camerino, d. 1610 in Lima), who was active in the Viceroyalty of Peru from 1575 until his death and is considered one of the founding fathers of colonial painting by the historiography of South American art. Through analyzing previously unpublished archival materials housed in Camerino (le Marche region), this essay reconstructs the historical context of his formative years as an artist by presenting new insights into his training in Le Marche region, followed by a five-year stay in Rome. The visual and devotional references he put together in Le Marche and Rome–where the name of Federico Zuccari stands out–formed the basis for Bitti’s Peruvian works.