This study surveys the fundamental technical approaches adopted by Renaissance artist Jacopo de’ Barbari in drafting his 1500 bird’s-eye view of Venice, as well as the ideological and military implications that accompanied the map’s production. In doing so, the authors point out some fundamental parallels between the masterpiece of Renaissance map-making and the current computer-supported digital representations of urban spaces. The historical sources indicate that de’ Barbari’s map was a composite image stitched together from numerous partial views; such partial views were already "digitized" and consequently mechanically reproduced and manipulated into one synoptic image whose sheer size and amount of detail was able to evoke in viewers an experience of virtual reality. Ultimately, the study challenges the rhetoric of newness that dominates current media studies by emphasizing the need to separate what is genuinely new in our everyday experiences of media from what has been seen before.