Dubrovnik and Venice are the most touristically overloaded cities in Europe: their rate of tourists per inhabitant makes them the most afflicted towns by overtourism. This awareness should lead us to rethink the tourism industry in the Adriatic Region, to decompress overbooked places and promote social and economic growth in (still) undeveloped tourist destinations. Wine is one of the motivations that leads tourists to choose a destination over others, also because food and wine tourism can connect visitors with local producers, thus local culture. This kind of experience can push toward new routes of cultural tourism, able to bring visitors to minor destinations of the Region, ideally reducing their stay in the main, crowded towns, to discover new, attractive territories and their culture. By investigating two archive collections, in Zadar and Venice State Archives, we are tracing wine trades between the two sides of the Adriatic in the seventeenth and eighteenth centuries. Combined with a critical analysis of previous attempts to promote cultural heritage of the Adriatic space, the ultimate goal of the research is to draw up an analytical proposal for new cultural tourism itineraries focused on wine aimed at Millennials, in the walk of these ancient commercial routes.