Background: Retirement is recognized as a factor influencing the ageing process. Today, virtual health coaching systems can play a pivotal role in supporting older adults’ active and healthy ageing. This study wants to answer two research questions: (1) What are the user requirements of a virtual coach (VC) based on an Embodied Conversational Agent (ECA) for motivating older adults in transition to retirement to adopt a healthy lifestyle? (2) How could a VC address the active and healthy ageing dimensions, even during COVID-19 times? Methods: Two-wave focus-groups with 60 end-users aged 55 and over and 27 follow-up telephone interviews were carried out in Austria, Italy and the Netherlands in 2019–2020. Qualitative data were analysed by way of framework analysis. Results: End-users suggest the VC should motivate older workers and retirees to practice physical activity, maintain social contacts and emotional well-being. The ECA should be reactive, customizable, expressive, sympathetic, not directive nor patronizing, with a pleasant and motivating language. The COVID-19 outbreak increased the users’ need for functions boosting community relationships and promoting emotional well-being. Conclusions: the VC can address the active and healthy ageing paradigm by increasing the chances of doing low-cost healthy activities at any time and in any place.