Using microdata on the 1995 cohort of Italian high school graduates, this paper studies the relationship between the type of high school attended (general versus technical; private versus public) and indicators of subsequent performance. Simultaneity issues that potentially bias this type of exercise are tackled by instrumental variables. Results indicate that the type of high school attended greatly depends upon the family of origin and prior school performance. General high schools are found to increase the probability of transition to university and to improve performance once at university. On the other hand, private high schools appear to be associated with lower academic performance. Technical schools improve the quality of the school-to-work transition, both in terms of participation and employment probabilities.