This section delves into the enduring connection between art, environment, and health, investigating the obstacles and possibilities encountered when integrating artistic interventions into healthcare programs, especially in Italy. It underscores the necessity for inventive methodologies to gauge the social impact of cultural policies in healthcare, elucidating the framework of the Horizon 2020 MESOC project. Examining various instances of best practices, it discerns diverse approaches by which artistic activities become part of healthcare settings. The section concludes by scrutinizing shared challenges and facilitating factors in the formulation of cross-sectoral initiatives within the domains of culture, health, and social involvement.