Walking is a mode of transport that offers many environmental and health benefits. Utilitarian walking refers to walking trips undertaken to fulfil routine purposes. The aim of this paper is to examine the extent to which walking is used as a transport mode for short urban trips in the city centers of Bologna and Porto and the barriers preventing utilitarian walking. Based on a questionnaire (n = 1117) administered in the two cities, results indicated that 21% of the individuals travel by foot, while 47% combine walking with other modes. This means that 68% of the daily trips to these city centers involve walking activity. From the overall trips, 84% were made to reach work and school/university. Statistical tests showed that utilitarian walkers were more likely to be females (p < 0.001) and undergraduates (p < 0.001). People from Bologna were more likely to engage in utilitarian walking than people from Porto (p < 0.001). Travel distance and time were the main barriers preventing people from engaging in utilitarian walking. The findings described in this paper provide a better understanding of utilitarian walking in the central areas of both cities, which can guide policies to promote healthier lifestyles and sustainable mobility.