The debate on territorial cohesion and spatial inequality recognises the role and influence different scales have on individuals’ opportunities with extended effects especially for young people’s life chances. In particular, a regional perspective into territorial disparities of socio-economic conditions and welfare in Europe provides a more fine-grained view on the existence of territorially diverging income and labour market conditions for youth that a national level analysis is not able to grasp. This paper focus on regional differences in school to work outcomes of young people using macro-panel data covering the period from 2005 until 2016. We use a plurality of indicators to study to what extent school to work transitions are better studied at regional level and to characterise those transitions in a more comprehensive way. Our findings demonstrate that there are huge differences both in the level and in the dispersion of young people’s school to work outcomes across European territories. This tells us that the allegedly assumed national homogeneity of transition systems can definitely not be taken for granted. Moreover, we show that the Great Recession had strong but differentiated impacts at regional level.