The fourteenth century Indian Ocean world saw a rapid increase in seaborne trade, which led to developing port cities and new centres of power. These port cities sometimes became the capitals of emergent states which broke away from the traditional pattern of landed states and established their own spheres of influence over land-and-sea realms. One such emergent state was the polity centred on Raigama and Kotte in southwestern Sri Lanka, which gained prominence in the region thanks to the port policies followed by its rulers, the Alakeshwara family. This research analyses the rise of this state in the context of the Indian Ocean custom of the ‘right of the port,’ which allowed merchant groups like the Alakeshwaras to establish taxation and sovereignty over an area. This also presents an alternative perspective from which the politics of the kingdoms of Sri Lanka can be reframed and understood, breaking away from the internal logic of ceremonial succession and historical inevitability.