This contribution is the follow up of a study started in 2020, which aimed at comparing two object-based learning methodologies—Artful Thinking AT and Visual Thinking Strategies VTS—in order to determine whether a strategy born in the academic sphere with the aim of enhancing critical thinking was as likely to produce well-being in work session participants as the practice created in the museum sphere. The theoretical underpinnings of this research can be found primarily in the pioneering work of Helen Chatterjee's team at UCL (UK) in exploring the role of museums in promoting well-being (Chatterjee & Noble, 2013). This strand of research has highlighted how interaction with art and cultural heritage can have positive effects on mental health and psychological wellbeing. This has paved the way for research into how technology can enhance these benefits, as also highlighted by studies on Object-Based Learning (Chatterjee & Kador,2021). The use of digital technologies for the enjoyment of cultural heritage is also linked to issues of social inclusion (Kinsley, 2016), and research on the connection between critical thinking and well-being (Tishman, Palmer, & Harvard Project Zero, 2006;) refer how technology can support this process through collaborative platforms and virtual learning environments, with benefits for motivation, engagement and a sense of belonging to a group-community (Fancourt & Finn, 2019). This research activity adopted a mixed comparative approach: quantitative through pre- and post-experience questionnaires (Umbrella toolkit, UCL) and qualitative through the observation of participants’ statements and interactions on the basis of the critical thinking evaluation grid (Poce, 2020), concluding that AT is a useful tool for the promotion of well-being as well as critical thinking, and that results from the online work sessions were similar to those carried out at the museum.in terms of engagement and perceived well-being.