In mid-fourteenth-century Japan, amid decades of civil unrest caused by a violent rivalry over imperial succession, three men embarked on journeys that would lead them to reimagine their world: the second Ashikaga shogun and general Yoshiakira (1330–1367), the Buddhist lay priest Sokyu (ca. 1350), and the statesman Nijo Yoshimoto (1320–1388). All three shared elite social status, political connections, and a deep engagement with poetry. Yoshiakira traveled from Kyoto to Sumiyoshi Shrine in Osaka to pray for poetic skill; Sokyu left his home in Kyushu and wandered for three years across Honshu, visiting sites celebrated in traditional waka poetry; and Yoshimoto, after fleeing an attack on his home in Kyoto, found refuge in distant Ojima and comfort in composing poetry surrounded by "the scene of an unfamiliar place." Their memoirs, written within a decade of each other, offer important insights into how their worldviews—formed by centuries of canonical literature and court traditions—were increasingly challenged by their encounters with new situations and territory, landscapes they would capture from perspectives of absence and erasure. An Unfamiliar Place examines how these three traveler-poets used both literal and metaphorical "unfamiliar places" as sites of expressive power, to not only explore novel ways of existing in and moving through the world, but also reassess their assumptions about the social and cultural significance of geographic space.