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Michael Pearson has contributed greatly to maritime history in the Indian Ocean World, focusing on what he calls the “littoral society.” He argues for the importance of observing how the land and the sea connect each other. Following his argument, this article explores agency in medieval Swahili port towns. Recent developments in archaeological studies have revealed the complex relationships between the land and the sea in East Africa. However, there are certain issues archaeological evidence could not explain. Drawing on archaeological studies as a reference and also studies on Southeast Asian ports for comparison, this article seeks to explore medieval Arabic literature, virtually the only available written material, to consider the case of the medieval Swahili coast.