In order to understand the context of the writings associated with the Kumano pilgrimage, this chapter begins by introducing the concept of Japanese travelogue as well as the places of worship and pilgrim roads in the Kii mountain range which were also inscribed on World Heritage list in 2004. It is important to underline the difference in social context between the early thirteenth and the early twenty-first centuries when attempting to assess whether the narratives written about the same walks actually have anything in common. The narrating of historical travel is not confined to diaries but is also found in poetry, adorned by pillow-words, and is even included in works of drama and Michiyuki, a poetic genre dealing with literary travels, including imaginary ones. The close link between travel writing and illustrations is still evident. The travelogue tradition is still very much alive today, as will be illustrated by reference to contemporary works on Kumano.