The origin of parkour can be dated back to George Hébert’s studies. It was created in France and quickly spread around the world. This motor discipline is commonly defined as “art du déplacement”, and its aim is to adapt one’s movements to the surrounding environment, both natural and urban. Parkour transforms towns from still and impersonal spaces into places for creativity, learning, and self-knowledge. In fact, a practitioner (before beginning to move) will continuously wonder about his motivations and his physical perceptions, converse with his fears, and look for his psychophysical balance. In 2019, the Italian Ministry of Health invited to consider unstructured activities to promote active life and make individual and collective gratification elements available. With this aim, parkour (as a mainly sensory–motor discipline) is very useful owing to its educational purposes, in particular when children are involved, because their approach to senses is still free from social and family conditioning. Parkour is a movement practice, which requires considerable physical, mental, and emotional training. We discuss the relationship between parkour and edgework (a socio-psychological concept about voluntary risk-taking; Lyng S., 1990) because parkour practitioners are exposed to risks that seem greater than what is socially acceptable. This study analyzes parkour as an outdoor activity, as an expression of flourishing (Nussbaum M, 2007) from the point of view of the urban jungle and as a denunciation of unsuitability of urbanization for the natural needs of the human being. We confirmed that the edgework approach was a very effective tool for practitioners to improve their specific skills and their personal lives. Parkour poses the questions; the practitioner’s aim is to find the answers.