Pedestrian Navigation Applications (PNAs) provide assistance in terms of self-localization, space recognition, and turn-by-turn navigation. The use, motivations and perceptions associated with these applications have been under investigated due to users being insufficiently involved in their design and development. This paper analyses the extent to which PNAs are used for assisting people to walk, the frequencies and reasons of using these applications, the perceptions about them, and the barriers preventing them from being used. The study is supported by a questionnaire (N = 1438) that was administered in Bologna (Italy) and Porto (Portugal). Results indicated that 42% of the respondents use PNAs mainly on an occasional basis to find locations and the shortest routes. Google Maps was the preferred navigation service. Statistical tests showed that PNAs were more likely to be used by younger adults and students. The lack of need was the main reason for not using these apps, due to the good spatial knowledge of the cities or the non-use of the pedestrian mode for regular trips. Respondents would like to have apps that are more accurate, usable, and adjusted to pedestrian navigation. The findings described in this paper could be helpful for future designs of PNAs, especially to match pedestrian needs more effectively and to enhance the role of these apps in promoting healthier and sustainable lifestyles.