In this article we explore how to play storytelling games with collections of artworks. First we propose a generic storytelling game, titled “Find the artwork behind the story!”, and we present the results of a user study that investigates the game’s affordances in different environments and setups, ranging from large exhibitions at a cultural center, to a casual home setting. We report a series of game-testing sessions, highlighting the differences between on-site and remote experiences and we reflect upon critical aspects of the game design, identifying key opportunities and requirements in each case. Then we focus on the “home game scenario” and we describe how we re-designed the game experience so as to address the increased interactivity and learning requirements revealed in this setting. We propose a hybrid board game experience that combines analogue and digital media, orchestrating the use of physical “Artwork Cards” along with digital narratives displayed on the players’ personal mobile or tablet devices. We present the game-authoring platform and the mobile client application that we have developed to support the creation and provision of the proposed game experiences. Finally, following a user-centered design approach, we report preliminary evaluation results of the game prototype using the focus group methodology.