Wine tourism in Italy, the largest wine producing country in the world, has achieved outstanding performance over recent years. However, various institutional, managerial, and professional delays in the field impede Italy from developing its full potential as a wine tourism destination, most likely because of the still unsatisfactory engagement of all possible stakeholders. A recent step forward has been the specific amendment regarding wine tourism provided by the 2018 Budget Law, anticipating regulatory norms for the sector. In this scenario, Italian wine routes, established by Law No. 268/1999 and consolidated by the law on vines and wine (Law No. 238/2016), should play a key role in the governance and management of the local wine tourism industry. However, the state of the industry presents opportunities and (above all) challenges. Our research contributes to exploring this scenario, providing evidence from the field and potential guidelines for development through territorial stakeholders' engagement.