This chapter begins with a general discussion of studying juvenile justice comparatively. It discusses descriptive, explanatory and interpretative enquiries and their relation to the challenges of finding equivalence, discovering what is salient and thinking reflexively. The chapter illustrates case study, it examines whether Italy has an especially lenient system of juvenile justice. In Italy, there are many fewer options for non-custodial sentences than are found in most other European juvenile justice systems. Juvenile justice in Italy was reshaped at the end of the 1980s through the introduction of measures that brought educational features to penal procedure. In addition, many of those who create descriptive taxonomies are interested in highlighting the differences between more or less interventionist approaches that lead to more or to less punitiveness. The chapter suggests that learning from other places is inextricably bound with learning about other places and that using descriptive, explanatory and interpretative approaches can help in this task.