This study explores whether various distance trips and age stereotypes affect tourists’ perceptions of tour leaders’ roles. This research also identifies the moderating effects regarding tour leader age stereotype, age in-group bias, and the respondents’ age on the perceived roles played by tour leaders. A total of 447 subjects participated in the study with a 2 (role-play scenarios: short-distance trip vs. long-distance trip) x 2 (appearances of the tour leader: middle-aged vs. young) between-subjects factorial design. The results showed that the respondents’ perceived roles of a middle-aged appearance tour leader were better than some young appearance counterparts’ components under short- and long-distance conditions. Furthermore, the tour leader age stereotype and age in-group bias could influence respondents’ perceptions of care and interactional and communicative dimensions. In addition, respondents’ age could affect the perceptions of some components of the tour leaders under short- and long-distance conditions.