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This article will track my own intellectual engagement with Michael Pearson’s wide-ranging scholarship (on topics that range from ports to Portugal) over a twenty-year span (1995-2015). Similar to Pearson, I began my academic career as a Goa (Indo-Portuguese) specialist and moved onto studying the Indian Ocean as a point of connection and comparison across aquatic terrains. I will take up certain “keywords” as a vocabulary of culture and society (following Raymond Williams, 1976) specific to Pearson’s oeuvre in order to show my conceptual development through his scholarship, and his important contributions to historiography and historical studies. Keywords will range from “corruption, corsairs and crowds” in 16th -17th century Portuguese India, to “ports, islands, the monsoon, and a whiff of the ozone” in the Indian Ocean world, and lastly to “hippies and tourism” in postcolonial Goa.