The aim of the current study was to explore perceptions of group-based walking and gather suggestions to inform the development of a group-based walking intervention among older adults in retirement villages. Twenty-four physically inactive residents (16 female, 8 male; age range: 69–88) and four managers from four retirement villages were interviewed. Inductive thematic analysis revealed six broad themes: lack of motivation, values versus constraints, fears and confidence, need for structure, creating a sense of belonging, and the physical environment as a double-edged sword. Proposed intervention strategies included using trained walk leaders, using small groups, planning for flexibility, setting attainable goals, creating a routine, creating opportunities for sharing experiences, and planning a variety of walks. Group-based walking programs may be used to promote physical activity but careful planning of such programs is needed to make them appealing and feasible to a diverse group of residents.