This paper aimed to investigate the relationship between young peoples' leisure time and risky behaviors. This was examined through a survey questionnaire constructed for the purposes of this research, which contained two scales: the Leisure Time Scale and the Risk Behavior Scale. A total of 204 secondary school students from the Republic of Croatia and the Republic of Italy participated in the survey on a voluntary basis. The research methodology included a descriptive analysis with percentages, frequencies, means, and standard deviations. Hypotheses were tested by inferential statistics including factor analysis, t-test, ANOVA test, and correlations. The results of the empirical part of the research indicate that young people spend their free time more often consuming entertaining and media content, and less in the family and educational environment. Young people with poorer school performance more often spend their free time in entertainment and media contexts, while Croats, compared to Italians, spend their free time more often in family and educational environments. Results were also obtained on the manifestation of severe and milder risky behaviors. No differences were identified with regard to student gender, legal guardian, and origin, but there were differences with regard to their age and school performance. Older respondents and those with lower school performance are more prone to manifest milder forms of risky behaviors compared to others. The correlation between young peoples' leisure time and risky behaviors was also established.