This study examined and compared walking satisfaction in three case study cities in Europe: Dortmund, Genoa, and Gothenburg as part of an EU project. By analyzing household survey data, we explored levels and determinants of walking satisfaction within and between the cities, using the Satisfaction with Travel Scale to measure walking satisfaction. The results show that levels of walking satisfaction differ between the cities, both overall and in terms of its sub-dimensions positive activation, deactivation and cognitive evaluation. This implies that different experiences are present when walking in different contexts. We also found that different factors influence walking satisfaction in different contexts. Accessibility and the social setting, in terms of walking in company or not, are important for walking satisfaction in all contexts. On city level, several differences in determinants were detected. These findings point at the importance of contextual settings in evaluations of walking satisfaction. In all three cities, we also found that walking satisfaction was significantly higher for trips which allow more flexibility, such as leisure or recreational walking, than for trips with a set destination. The findings expand the existing body of knowledge about determinants of walking satisfaction in different urban settings and provides vital insights for urban planning and policies determined to foster walking-friendly and satisfactory local urban environments.