The immersion of societies in the digital and networked age has led to an increase of opportunities for young people to learn across countless face-to-face and online contexts. However, youth disaffection towards school remains high and access to opportunities across and within countries is remarkably unequal. This article builds on the results of two ethnographic case studies conducted in Spain and the learning stories narrated by 22 youth about their transitions across home, school, spare time, extracurricular activities, trips and virtual environments. The analysis of the stories show how young people establish connections and feel tensions across their experiences, creating continuities and discontinuities that are key for their learning. It also evidence that secondary school is only one node of the big sociocultural network through which young people learn. Building on the results, the conclusions raise the question: might a better understanding of learning trajectories favor a more inclusive educational system?