In this paper, we present: (1) a theoretical approach to examine older people’s pattern of outdoor activities based on the concept of ‘personal projects’; (2) different research instruments—Personal Activity Questionnaire and an Activity Diary—designed to capture the different aspects involved in the analysis of outdoor activities; (3) the results of different pieces of research using these diverse instruments. Overall, the results show that outdoor activities are seen as meaningful personal projects for older people, associated with their health and psychological well-being. Current development and revisions in the research instruments are also presented and discussed.