In this article, we showcase the pilot scenario of The Trojan War, an educational self-directed game that combines text inspired by ancient Greek (as well as Roman) literature with graphics based on the ‘Geometric style’, an authentic Greek style of painting contemporary with the composition of the Homeric epics. Our game uses interactive scenarios to support active learning strategies of students interested in Classical Studies in both tertiary and secondary education. Players can take on the role of key characters, making choices that can prevent, start, or stop the Trojan War, as well as determine their own personal outcomes. The learners are thus presented with the opportunity to explore alternative pathways to rewrite the history of the War. In the process, they can apply their subject knowledge and develop their intellectual and critical skills. They also become familiar with a distinctive and expressive early Greek artistic style, the so-called Geometric. Rather than focusing on winning, the game aims to give students the opportunity to engage with important ideas and values of ancient Greek culture by exploring multiple perspectives on the topic. It also provides a valuable lesson on the potentially wide-ranging consequences of individual choices, which is a core element of responsible citizenship.