This study looked at the role of parental factors in adolescent gambling. It also examined whether adolescents’ personal characteristics might explain the effects of parental factors on gambling behaviour. Participants were 1,848 Italian students aged 12–14 years old. Slightly over half (55.7%) reported gambling in the last 12 months. Parental gambling; gambling with parents; parental permissiveness to gamble, smoke, and drink alcohol; and perceived gambling among friends were all related to higher likelihood of gambling. In terms of personal characteristics, adolescents’ performance beliefs about gambling (e.g., gambling is a way to become rich), positive attitudes towards gambling, and sensation seeking explained the effects of parental gambling and gambling with parents on their own gambling.