In the eleventh century, the Baltic Sea area became a target for Christian crusades – religious enterprises combined with Scandinavian colonial ambitions. The countries of the Baltic Rim were converted, colonised and Europeanised, visibly expressed by, among other things, changed practices of exchange and the introduction of domestic coinages. Less discussed from a crusading and colonial perspective is the large island of Gotland. A wealthy maritime and trade node in the middle of the Baltic, it was by tradition tied to eastern Sweden but also held an autonomous position that is revealed archaeologically through differences in material culture. The chapter investigates the Gotlander’s strategies for maintaining their old ways and networks while trying to steer clear of new demands and tangible threats; the important part coins played in this; and how an analysis of colonial processes may improve the understanding of how local history unfolded.