This paper will explore the diffusion of the motif of “περιδιάβαση” in early vernacular poetry (Βασίλειος Διγενής Ακρίτης, Θησηίς, Chansons populaires), as well in Cretan Renaissance poetry (Σαχλίκης, Έπαινος των γυναικών, Βοσκοπούλα, Πανώρια, Ερωφίλη, Ερωτόκριτος) by giving examples from the texts. The examples differ both thematically and aesthetically. Some of them refer to a walkthrough, to a return to the countryside. Furthermore, what appears to dominate and basically plays the main role in the narrative is walking in the mountains (for example on Mount Ψηλορείτης in the theatrical comedy Πανώρια). On the other hand, the poet Sachlikis wanders in the city. He remains within an urban terrain. We will try to trace in his texts the way in which the urban is depicted. There will also be an effort to compare the Greek texts with Western European examples of the same period and trace the most celebrated feature of Homer’s Odyssey (Ulysses is the hero of περιδιάβασης) in its metapoetic function, one that is conspicuous in the epic’s reflection on other songs drawn from the repertoire of oral Byzantine poetry, like the poem Βασίλειος Διγενής Ακρίτης (Βασίλειος is also a hero of περιδιάβασης). At a historical conjuncture when the “death of the past” is promoted and which is dominated by a fragmented and ahistorical present, this paper suggests that any move forward to the future will have to negotiate the past and literary tradition in a historical, ideological and aesthetic manner.