Road accidents represent the primary cause of death among young drivers. To understand the emerging issue of young drivers’ involvement in traffic accidents abroad, risk-taking behaviors were investigated in familiar and unfamiliar driving situations. Twenty-two young Chinese drivers completed a road regulation test followed by a simulated test drive. The number of traffic violations and accidents in familiar and unfamiliar driving intersections were correlated to road regulation knowledge, risk perception scores and to self-assessment of driving skills. Significant number of mistakes was found in risk-taking situations, regardless of the familiarity of the situation, especially for drivers that presented high ratings of self-assessed driving skills. Results show that risk-taking behaviors while driving in unfamiliar conditions are mediated by psychological factors, like self-assessment of being a good driver, more than the actual knowledge of road regulation rules. Implications for international driving can be considered for future research development.