By drawing on phenomenological notions, this paper offers a “middle way” reading of Bashō’s travelogues that accentuates their religious, rather than merely aesthetical purpose, which is to transmit the Buddha Dharma. Two distinctive poetic traditions of Bashō interpretation exist: the Zen-inflected, monologic, and individualist tradition and the intertextual or dialogical interpretation. One way to reconcile these two strains in Bashō’s poetics is to see his haikai through the lens of mind-to-mind transmission of light. This “middle way” interpretation traces a double movement of phenomenological reduction through two travelogues: first, by showing how home departure entails freeing the mind of fixity and, second, by suggesting that mind-to-mind transmission removes the ambition to find refuge in peak experiences, just as it resists being reduced to parodic subversion of reigning cultural values. In the Buddhist lineage, the heart of transmission rests neither upon conservation nor upon rejection of poetic essences but, rather, lies in transforming haikai into medicine, which is efficacious for the process of awakening.