Countries’ institutional configurations and structural characteristics play an important role in shaping transitions from school to work. Recent empirical evidence shows significant regional and territorial differences in youth unemployment and labor market participation. Along this research strand, we argue in favor of a place-sensitive approach to youth labor market integration in order to address the regional disparities of young people’s opportunities. In order to investigate the synergic effect of different contextual configurations, we construct a composite measure, namely, the youth labor market integration (YLMI) index. This considers a wide range of indicators of the access, exclusion, and duration of the transition into employment at the regional level. The YLMI index allows cross-regional and longitudinal comparisons of the European Union (EU) local labor markets and youth employment opportunities.