The navigational activities of orienteers involved in two training tasks were compared in this study, which looked for specific measures to help in training and used a course-of-action research approach. Eight beginners volunteered to take part. Two types of data were collected: (a) recorded video and audio data using camera glasses for each participant, and (b) verbalization data collected during individual self-confrontation interviews. Processing the qualitative data involved reconstructing the participants’ course-of-experience according to semiotic analysis of the course of action. A complementary statistical analysis between the two tasks noted occurrences with respect to map reading. Findings showed both similar and different forms of navigating activity between the two tasks, related to specific phases of the course, the difficulty, and the time constraint—giving importance either to the map and the terrain or to the control flag. These different modes are discussed according to the significant constraints of the environment and the use of heuristics. Recommendations are made for improving the teaching and learning of orienteering.