Focusing on a selection of Rabindranath Tagore’s essays, lectures, and a few of his creative works, this essay draws attention to the spiritual orientation of Tagore’s transnationalism. In his vast and multifaceted writings, Tagore offers an alternative vision of transnational union of humanity, different from and often resistant to nationalist distributions of human relationship. Through close readings of Tagore’s works, this essay complicates Orientalist notions of the East-West polarities. While strongly opposing Western imperialist ideology, Tagore was always frank about his trust in and indebtedness to the liberal humanist values of the West. On the other hand, despite upholding Indian or Eastern spirituality, he was critically aware of the social and political crises of the contemporary East. A large volume of his works betrays his scepticism about any political solution to national and international problems. What he promotes is a spiritual concord of the best in Western and Eastern cultures, connecting the liberal humanist conscience of the West with the harmonizing, all-inclusive spiritual wisdom of the East. Neither completely secular nor thoroughly religious in an institutional sense, the transnationalist spirituality of Tagore bridges the gap between the secular humanism of Western modernity and the mystic–religious spirituality of Eastern antiquity, offering nuanced perspectives on both.