By investigating 321 smuggling vessels that travelled between the Faroe Isles and the British Isles between 1775 and 1785, this article explores the regionality and seasonality of illegal trade in the north Atlantic. The article centres on a neglected oceanic region, thereby inverting historical geographies, shifting the focus from port centres like London and Copenhagen to the Scottish Northern and Western Isles, as well as the Faroe Islands. Epitomizing the ‘dichotomy of insularity’, in the eighteenth century these areas were located along maritime highways of global trade, and illegal trade flourished there, despite their challenging location. The article demonstrates that this illegal trade had different seasonal cycles from those of legal trade. While legal trade halted in the winter season, illegal trade continued throughout. Linking illegal maritime activities to more lawful ones, like fishing, the article suggests that the recurring nature of the contraband trade ought to be understood in relation to the broader coastal culture, in which maritime knowledge was circulated and the local relationship to the sea defined. The study suggests that illegal trade should be viewed not merely as an extension of globalization but as a rooted phenomenon, which developed in unison with the local environment.