The school-to-work transition is one of the trickiest steps in the life cycle of an individual because when young people complete their education and enter the labor market, they have to compete to attain a job while lacking the job experience or skills required by employers. Across European countries, the school-to-work transition shows very different characteristics and durations, stemming from, among other factors, (1) the different provisions of services at the country level to help young people become oriented in the labor market, (2) different historical backgrounds, and even (3) the different capacities of education systems to provide the skills required by employers, despite the efforts to homogenize the national education systems, which started with the Bologna process. In this paper, we aim to compare various programs implemented within formal education at the macro-level in Italy, Moldova, and Latvia, three rather different countries in Europe, that have the goal of helping young people during various stages of this transition. The conclusion we can draw is that each of these countries needs to adopt a coordinated and integrated strategy of reforms aimed at (a) preventing early school drop-outs; (b) incentivizing the attainment of a university degree; (c) reforming school curricula; (d) closing the gap between education systems and labor market requirements; and (e) improving the services that help young people during the school-to-work transition.