Research on environmental psychology has shown that humans perceive environments not solely by relating to their physical features but also in reference to their affective qualities. Without regard to the impact these affective perceptions might have on the decision-making process during navigation tasks, most of the current web or mobile pedestrian routing services employ distance or time optimized algorithms and often fail to fully meet the needs of the users. This study wishes to introduce a pragmatic approach of harnessing Location-Based Social Media as a potent and readily available resource for extracting people’s affective perceptions of the environment. Furthermore, it proposes a method to aggregate and model the extracted information for the enhancement of pedestrian route planning and identifies the main issues and challenges the nature of these data raises.