While Iacopo Sannazaro (1458–1530) is mostly known for his Arcadia (1504), his Christian epic De partu Virginis (1526) was widely read by his contemporaries,  prompting them to label him as "another Virgil." This essay examines Sannazaro's portrayal of Mary in the De Partu. Many of Sannazaro's contemporaries took issue with the fact that the moment of Annunciation was likened by the poet to a young girl fearing rape by pirates. Closer examination of other Christian epics in the period, however, along with contemporary preaching traditions and the visual arts, demonstrates that Sannazaro’s portrayal was not as heterodox as it initially appears. Indeed, when seen in this context, Sannazaro’s Mary emerges as a bolder and more independent figure than she was in previous literary and visual depictions.