The journey is for us and was for Saigyo an impermanent condition of movement, but aside from this essential similarity, our conventional conception and Saigyo’s diverge. Whereas we embark on a journey to get to a destination, ultimately returning to our home, Saigyo transcends all such structures and anchors by dwelling permanently in the condition of the journey. That is, the journey itself is home for him. It would be easy to argue that he is no more than nature poet, drawn into a lifestyle of traveling because of its privileged connection with the natural. This stance has been argued in the past, and convincingly grounded in the strong value of nature in Japanese literary tradition. However, framing him this way overlooks the deep spiritual beliefs and unique cultural influences that inspire his work and push him to along his wandering way. In this essay I seek to understand the connections between Saigyo’s fundamental spiritual beliefs and poetry, while focusing on how and why a wandering lifestyle is integral to his life and work. I believe he expresses through his poetry and wandering lifestyle the realization and acceptance of what he feels to be the absolute truth and beauty of impermanence, as symbolically and actually present in nature.