Users of public transit tend to avoid certain routes because they dislike particular aspects, or gravitate towards a particular mode because it is familiar, or because it “feels right”. This type of navigation can be described as ‘wayfeeling’, or letting one's senses guide the way. The concept of wayfeeling is integral to understanding how public transit space is used, and underscores the importance of emotional wellbeing within these spaces. But how does one determine what wayfeeling is and when it is being performed? The aim of this paper is to illuminate how emotional wellbeing affects navigational behaviors through the act of wayfeeling. The study uses participant experiences of a Destination-Task Investigation (DTI) in Munich's public transit system. Included in the DTI, participants were asked to draw their navigational journey, and then asked to highlight the sections they found positive, neutral, and negative. The study revealed that the act of navigating a transit space evokes strong emotional reactions from participants, especially as they had more negative experiences in transfer areas, and felt more positive in familiar spaces. Most importantly, negative events during the DTI overshadowed the overall perception of their journey which lead to an overall negative opinion of their experience.