This study elucidates the relationships between the elements that visitors gaze at in a historical district and the objectives perceived to have been achieved. This study differs from previous studies on visitors’ evaluations of historical districts (carried out using the theoretical frameworks and methods of architectural/environmental psychology), because the research focuses on interpersonal differences in tourist gazes. Research was conducted between 09:30 and 14:00 on July 13, 2013 in front of the railway station, near the tourist information center in Sanmachi, and around the entrance to and in the waiting room of Takayama Jinya. One thousand visitors to Takayama city, Japan were asked to complete and return questionnaires, using stamped, pre-addressed envelopes. They were first asked whether they had seen 19 elements, and then asked to rate the impressiveness of those they had seen. Respondents also rated the extent to which seven objectives related to learning and interaction had been achieved during their visits. The findings suggest that visitors who gaze at various elements may strongly perceive opportunities to achieve their objectives, that is, learning about a destination and interacting with other people. For visitors who specifically focus on local elements that do not relate to people, opportunities for learning may not be curtailed, but then again, the chances to interact with others may not necessarily be facilitated. Gazing at the multifaceted aspects of a historical district appears to foster a visitor’s understanding of the district. Drawing upon these findings, future studies should investigate the effects of visitors’ pretravel motives on their gaze.