Crowding studies have a long history in urban geography and environmental psychology, although results are mixed at best. While crowding is found to influence residential quality and visitor experience and crowding perception models show some agreement on influential determinants, research is typically limited to a single setting, therefore minimising generalisability. To account for contextual effects, this paper tested a crowding perception model in two study areas: Amsterdam, the Netherlands, and Antwerp, Belgium. The results confirm that while most variables from earlier studies are significant, their effect on crowding perception depends largely on environmental context, with elements such as street layout, primary functionality of the area, and local culture affecting strength and direction of the relationship. The study reveals the importance of a case based approach to crowding perception, while demonstrating the overall applicability of the methodology and the possibilities of comparative analyses to suggest policy recommendations for specific areas.