We explored the relationship between cultural and social participation, physical activity, and well-being in a group of residents of the metropolitan area of Naples, Italy and the role that resilience plays in this relationship. Naples offers a remarkable urban environment with the potentially beneficial psychological effects of outstanding natural beauty, and one of the world’s most impressive repositories of tangible and intangible cultural heritage. However, Naples was also, and still is, heavily affected by the 2008 economic crisis, in addition to preexisting social and economic issues. The major finding of this study is that, despite this highly contrasting urban environment, the combination of physical activity and engagement in social and cultural activities has a positive effect on subjective (self-reported) psychological well-being (SPWB) in a group of residents, and that resilience mediates this relationship.