Ageing is a relevant and urgent priority on the agenda of all the most industrialized countries. Ageing is harming the sustainability over time of the national healthcare systems as we know them nowadays. While policymakers are paying major attention to chronic care and the emerging new needs of patients who are aged 60+, less light has been shed on how to enable population-wide Healthy Ageing initiatives that offer the opportunity to postpone the need of institutionalized care and thus guarantee a longer healthy life to elderly. This study aims at furthering the debate about Healthy Ageing initiatives for elderly aged 60+ by shedding new light on the behavioural determinants of elderly’s intention to use a personalized, artificial intelligence-enabled, virtual coaching system for healthy ageing. Being the use of these systems based on individual “voluntariness”, understanding what might enable or inhibit such behaviour is of paramount importance for policymakers, professionals and developers. In fact, recent evidence shows that, despite the demonstrated benefits of these systems, the level of adoption among citizens aged 60+ falls far short of the expectations. This study develops and empirically tests an original model that, adopting the Technology Acceptance Model (TAM) as overarching theory, adds three other explanatory variables, i.e. Subjective Norm, Health Literacy and Information Technology (IT) Literacy. This study has been carried out within the NESTORE H2020 research project (ID 769643). Data from 436 Italian citizens aged 60+ were collected to test the hypotheses via Structural Equation Modelling. Results confirmed that Intention to Use a virtual coaching system is explained by Perceived Ease of Use and Perceived Usefulness. While Subjective Norm was found to have an indirect influence. Health Literacy has a negative effect on the Perceived Usefulness. Finally, IT Literacy positively influenced Intention to Use through the partial mediation of Perceived Ease of Use. Our results contribute to theory by unfolding the role played by Subjective Norm, Health and IT Literacy, being the last two factors at the core of numerous improvement strategies. With respect to practice, the study offers implications to different stakeholders to facilitate the adoption of digital technologies for healthy ageing.