Considering a limited number of relevant personality measures (e.g., sensation seeking, impulsivity, locus of control, anxiety and altruism), the present study aimed to identify subtypes of drivers in an Italian sample of 207 adolescents aged 14–15 (52.7% girls) with heterogeneous moped riding experiences. Subtypes were compared on the basis of both self-report driving behaviors and two measures extracted from students’ performances on a moped simulator employing a specifically developed Rasch-based method. On the basis of cluster analysis, three subgroups were identified (profiles A, B, C). Profile B was characterized by high levels of sensation seeking and impulsivity, and low levels of altruism and anxiety. It showed high risk propensity considering both self-report and simulator measures. Profile A consisted of mostly females and was characterized by high levels of anxiety, externality and low levels of sensation seeking and altruism. While showing cautious driving behaviors, it did not differ from profile B in terms of crash involvement. Profile C was characterized by high levels of altruism and a more internal orientation; it showed the safest driving attitude.A relevant feature of this study is the direct assessment of driving behaviors by means of simulation performances, which nonetheless showed high concordance with self-report data. Congruence of our findings with previous studies on older and more experienced samples is discussed, along with the use of simulation, in the light of future perspective for research.