The exponential increase in the ageing population in comparison to other age groups is noticeable. Senior citizens are considered a disadvantaged group who experiences social and digital inequalities, tending to have an inactive lifestyle that impairs wellbeing. Information and communication technologies, and specifically gamified ones, can promote active and healthy ageing by limiting social isolation and availing their specific needs and preferences to engage in social, cognitive, and physical activities. Cyclotourism emerges as an activity that can be used to foster improvements in senior citizens’ quality of life, thus being the aim of this paper to assess the impact of game elements for active and healthy ageing. A total of 50 cyclotourists aged 50 to 75 years old, divided into experimental group and comparison group, were involved in the activity of a cycling tour with and without gamification. Prior to and during the tests, the PANAS and EQ-5D-5L scales, were used to evaluate the positive and negative affect and health perception of participants. In addition, an extended technology acceptance questionnaire evaluated the gamified technology preference. Findings suggest a positive impact in the use of gamified senior cyclotourism. It is possible to learn from these participants that they preferred to practice cyclotourism with gamification, being referred to steer positive emotions, decrease negative affect, and contribute to the perception of oneself as healthier. Moreover, by underlining the fun and behavioral goal toward sustainable active and healthy ageing, they highlighted the usefulness and easiness of gamification in cyclotourism.