A key concern in an ageing society is citizens’ mobility. As populations age, disability impairments can affect active ageing, health-related wellbeing and quality of life. In this paper, we present the on-going research project SeriousGiggle—Game-based learning for triggering active ageing. Its goal is to assess the potential of game-based learning for active ageing and contribute to a sense of wellbeing and quality of life. It also seeks to improve the mobility of older adults by creating a set of journey plans with route guidance that are rated in terms of safety, community support, environment and age-friendliness. Drawn on our field work with 33 co-designers, 40 end users and 10 semi-structured interviews with Subject Matter Experts, we identify a set of necessary design requirements to an Age-friendly Playable City. This study recommends the use of gamification and playful techniques to engage the end-users to provide information about local traffic signs, pavement conditions, wayfinding and, therefore, help to create route guidance and walking assistance that are personalized to older adults’ context in terms of location, travel fitness, mobility impairments and motivations.