The topic of distance is central in the Renaissance and in the contemporary discussion on pictorial perspective. In the 15th century, Piero della Francesca offered the first definition of perspective as a ‘science of distances’. However, Piero recognized the limits of central perspective, which are defined by the distance of the observer from the art work and the dimensions of the pictorial surface. Facing the problem of the so-called ‘marginal aberrations’, Piero produced a more unstable and dynamic perspective in order to maintain the truthfulness of perspective itself in the gaze of an active observer. This ‘virtualized’ perspective is one of the main interests of contemporary Avant-garde and especially of cubism, and reaches, also through Post Avant-garde, Emilio Tadini. In the 20th century, Tadini proposed a new reflection about the relationship between distance and perspective. His essays and paintings show some analogies with Piero della Francesca’s mathematical and art work, even if in them the destabilization of perspective produced by Piero is brought to its extreme, and distances are rethought almost completely in a nonlinear sense and as depending mainly on the visual-intellectual action of the observer, thanks also to the references to the oniric language and to the narrative structure of the fairy tale.