The aim of this paper is to contribute to the discussion of expertise and skilled movement in sport by analysing the bodily practice of learning a new movement at a high level of skill in parkour. Based on Sennett’s theory of craftsmanship and an ethnographic field study with experienced practitioners, the analysis offers insight into the skilful, contextual and unique practice of parkour, and contributes to the renewed discussion of consciousness in sport at a high level of skill. With Sennett’s concept of craftsmanship, it is possible to describe and grasp important aspects of obstacles put up, repetitions and material consciousness in developing perceptual and physical skills in parkour. The parkour craftsmen conduct a constant dialogue between concrete, material practices and thinking. It is argued in the article that Sennett’s ideas about craftsmanship are, in many ways, similar to Dreyfus and Dreyfus’ concept of mastery, but are less elitist and exclusive than the theory of skill acquisition. The parkour craftsmen add a critical cultural perspective to the academic field of skills and expertise in sport. They furthermore offer insight into the ontology of play, and how it plays an important role in developing skills at a high level.