In the 1920s when the Japanese empire was pushing its borders outwards, a significant number of Japanese civilians moved out of the Japanese archipelago to settle in or travel through its newly acquired territories. The encounter with the foreign landscape and the people who lived there took various forms. Through the analysis of poetic images characterizing the poets’ vision of “the other”, this article examines the ambivalent nature of the experience shared by young Japanese poets as they faced the realities of Japanese colonialism. I focus particularly on the poetic works by Anzai Fuyue and his fellow poets in a journal called A, published in Dalian, a port city at the tip of Liaotung Peninsula, which had been handed over by Russia in 1905 following the Russo-Japanese War. The vision of these settler poets is then briefly compared with that of another poet, Kaneko Mitsuharu, who traveled through the port cities in the Southern Pacific. The stark contrast in their respective visions of the local cultures suggests the strong self-colonizing motive on the part of the settler poets, who were struggling to acquire a colonialist perspective while concealing their own colonial unconsciousness.