In just a few decades, South Europe has become one of the most important destination areas for migratory flows coming from high emigration countries. The immigrant labour market integration in this area, however, differs significantly compared to the experience of older Centre-North European receiving countries. Although many cross-national studies have examined the role of some macroinstitutional variables that may affect the process of immigrant integration, the main reason for these differences seems to be due to the characteristics of the labour market. Italy may prove an important case study to explore this issue in greater depth, given that within the same institutional context, the labour market performances, structure and informal regulation differ significantly at a territorial level, with many Northern regions more comparable to Centre-North European countries, while those of South highlighting Mediterranean characteristics. Indeed, the aim of this study is to verify if, and to what extent, the differentiation of the labour market characteristics influence the modalities of immigrant socio-economic insertion also at a regional level within the same country. In particular, it focuses on the relationship with native labour forces and the so-called ethnic penalty, namely the differences between immigrants and natives emerging in the labour market performances when as many individual characteristics as possible are taken into account. The results of the multivariate analysis carried out confirm the existence of a trade-off among the Italian regions similarly to what is found in the comparison between South and Centre-North Europe: immigrants have better employment entry chance where the size of the secondary labour market is bigger, but at their expense in terms of job quality. However, gender specificities emerge too, making some clarifications necessary.