Heritage tourism is becoming more and more in demand for the tourists who are expecting a more authentic experience in their destination. Dubrovnik’s rich cultural and historical heritage makes it a viable location for the implementation of a medieval festival. A medieval festival in Dubrovnik would thus provide benefits to both tourists and hosts. The issues with organizing any kind of a manifestation are related to audience engagement and stakeholders’ cost/benefits. A viability research has been undertaken in order to determine which format and content would be the most well received. This research includes the comparative analysis of existing medieval festivals, an interview with a travel expert, and a survey taken on 195 participants. The research shows that the participants prefer arts and crafts among the options presented in addition to participating in a medieval feast, which has confirmed the initial suppositions. These initial suppositions were based on the historical aspect of Dubrovnik, the impact of the filming of Game of Thrones on the city of Dubrovnik, and analysis of how the implementation of creative tourism in a context of a medieval festival while enhancing the importance of heritage tourism. Based on this information, further analysis has shown that there is room for this festival. The implementation of this festival would extend the tourist season in Dubrovnik area while providing a fun and educational experience to the visitors with large financial benefits to the stakeholders.