Global historians have contributed greatly to reconfiguring our understanding of the early modern world. An emphasis has broadly emerged in current scholarship on the long-distance circulation of people and goods and cross-cultural exchange of knowledge with overseas empires usually described as major vectors of global interaction. This article corrects and complicates such an interpretation by calling attention to the periodic interruption of the main lines of maritime communication that many port cities around the world experienced every year and what this meant to their inhabitants. In particular, it focuses on the seasonality of the Portuguese Empire in monsoon Asia during the sixteenth and first half of the seventeenth centuries. This specific case is approached through a combination of ecological history, labour history, and the history of emotions. Its general significance is further illuminated by extensive use of comparison with examples related to other empires across the Indian and Pacific oceans.