Eastern Veneto is characterized by architectural sites and remains of fortified structures, in a rural landscape with a significant wine production. If compared to Eastern Friuli and nearby Slovenia, it shows a major deficit with regard to the tourist promotion of thematic routes evoking the important and fascinating historical-artistic remains of the Middle Ages. Over the last few years the Town of Portogruaro has carried out several interventions to recover and enhance its own image. Yet, the lack of an effective coordination - at supramunicipal level - of the initiatives aimed at fostering the so-called thematic tourism (which can be implemented through museum routes and itineraries) prevents an efficient connection between the historical and cultural elements of the territory dating back to the Middle Ages, such as the Fratta Castle, famous for its charming garden of Mars and Flora. The project aims therefore at testing and promoting a cultural-tourist route in search of fortified cities and castles and is connected with the enhancement of the local vinegrowing and wine-making activities. The initiative has been entrusted with a crossborder working party, made of teachers and guides who have the task of planning and creating operational synergies in their respective territories. The historical and architectural heritage of Eastern Veneto also has a crucial educational value that will be the object of an animation pilot project directed to kindergarten and elementary school children.