Why and how to teach skateboarding is at the heart of this chapter. It is important to ponder these questions as skateboarding expands into the mainstream sports realm and teaching skateboarding is used as an approach to learning many other things apart from skateboarding, such as desired social skills and cultural norms. This chapter suggests that movement literacy, with its four features of feel, explore, collaborate and assess, is a viable route to work pedagogically with teaching and learning skateboarding. The features resonate with cultural traits in skateboarding and are sufficiently open yet distinct. The chapter answers the question: what do skateboarders do, and how can we learn from them? It may be read as a pedagogical credo founded on pedagogical thinking and empirical research.