Serious games are used in the field of cultural heritage as a means to transmit cultural knowledge and enable an experiential contact with cultural content. The authors' aim is to investigate whether a game design exploiting the less used combination of complex storytelling, endogenous cooperation, and competition has the potential to sufficiently convey cultural content. More specifically, through four game interventions, it was investigated how a story-driven board game functions with teenage and adult users alike. A mixed research methodology was followed in all game sessions and data were collected through observation, semi-structured group interviews, and short questionnaires. Findings confirmed the playability of the suggested design and the potential to amuse players while providing learning gains and engagement with cultural content. Nevertheless, further evaluation in formal and non-formal educational settings is essential to validate our conclusions.