This paper discusses the results of regular evaluations of two Cultural Routes of the Council of Europe programme – Follow the Vikings (focusing on the heritage of the Vikings) and THE HANSA (featuring the heritage of the Hanseatic League). These evaluations are conducted by the author as a commissioned independent expert in 2022 and 2023. Geographically both of these routes are located primarily in the Northern and Central Europe. Historically, the routes refer to the early medieval and late medieval periods, with frequent overlaps in terms of geographic locations and touristic representations. The data is gathered through field visits, observations, interviews and a survey among the route representatives. Following the discussions within heritage and tourism studies, theoretically this paper critically discusses the production of heritage through/for tourist routes. Additionally, it reflects on the challenges of the top-down route development as a way to achieve political goals of European transboundary cooperation enhancement - with tourism being its key ‘driver’ and expected outcome. The results of the evaluation demonstrate the challenging realities of bringing a tourist route to life through top-down initiatives, while the difference between geographical routes, cooperation networks and digital storytelling becomes blurred. Additionally, the impact of a route branding on the tourism development and tourist decision making remains questionable.