This article focuses on Tagore's translations of medieval saint-poets, writing in different Indian languages, to examine his attempts at "impossible" boundary crossings, from the medieval to the modern, the local to the transregional, and the sacred to the literary. These translations are considered in terms of multilinguality, vernacularization and the democratization of literature, collaborative translation, and Tagore's contribution to the ongoing process of constructing a South Asian "modernity" for his own times. They destabilize distinctions between "classical" and "popular", secular and sacred, erotic and mystical, textual and performative. They can be read as "transcreations", often involving unorthodox collaborative methods. They challenge conventional translation theories privileging fidelity, singular authorship and the authority of the "original". Tagore's translations provide a dynamic model for a potential contemporary rethinking of the role of translation in South Asian literary history.