This book is a collection of essays that map the epistemic and literary engagement of India with Latin America and the Caribbean with the aim to reflect upon the discourses these regions have generated vis-à-vis of each other. The essays arise from papers presented by renowned writers, intellectuals, diplomats and artists at an International Conference on the cross-cultural experiences between Latin America, Caribbean and India, organized by the India International Centre–International Research Division, New Delhi, in February 2023. In recent years, these two regions have become important actors of the Global South which is not just a political and economic project, but also a location to unravel unexplored knowledges about each other. The essays traverse the manifold historical and cultural links that have existed between the two regions conventionally considered as distant and assumed to be historically mediated through colonial and neo-colonial powers. Episodes of this wide and intense exchange have been studied in silos, but when presented in juxtaposition, begin to show patterns of connections in what emerges as a transcontinental dialogic relationship, which the book uncovers and reconstructs. The themes explored include the rich and diverse civilizational, cultural, and literary landscapes, mutual reception and influence of intellectual traditions, the Indian diaspora in the Caribbean region, and the cultural bridges between the two regions. While tracing linkages through history, the volume also directs our gaze towards a present animated by mutual interest and transcultural fertilization.