Cannabis use is increasingly prevalent among young adults in Canada. Due to cannabis’ impairment effects, driving under the influence of cannabis has recently developed into a traffic-safety concern, yet little is known about the specific circumstances and factors characterizing this behavior among young people. In this study, we interviewed a sample of university students (n = 45; age 18–28 years) in Toronto who had driven a car after cannabis use in the past year. The study collected information on respondents’ sociodemographic characteristics, cannabis and other drug use, cannabis use and driving (CUD) experiences, law enforcement and accident exposure, perceptions of cannabis and alcohol impairment effects as well as future anticipated substance use and driving behaviors. Results indicated that: CUD originated primarily from social settings; that impairment risks from cannabis were perceived to be low; and that the level of anticipated future CUD was high. Furthermore, high frequency of CUD in the past year was associated with high frequency of cannabis use. Interventions aiming at CUD among young people need to be anchored in the specific sociocultural settings of this behavior; targeted information needs to address cannabis’ impairment potential for driving; possibilities for harm-reduction measures for CUD need to be considered.