Despite attention to sustainability growing in the last decade in the wine sector, the rate of association with wine sustainability programs still appears to be limited. This is mainly related to the uncertainty about the economic benefits related to the implementation of sustainable best practices. In this regard, some studies highlighted that the presence of professionals capable of managing the requirements promoted by the standards generally leads to a positive perception of their impact on the economic performances of companies. Therefore, to encourage participation in sustainability programs, the adoption of a collaborative approach to share the skills and knowledge necessary to manage the transition from a conventional organization to a sustainable one seems to be a functional strategy. This paper presents the Prosecco Sustainability Project as a case study to investigate how a structured set of activities must be deployed through a participatory/collaborative approach to significantly improve the level of sustainability of a wide and heterogeneous community of grape and wine producers. The case study highlights that the collaboration between different actors and the guidance from a coordinating figure capable of fostering dialogue and cooperation among the various stakeholders represent key elements to the large-scale deployment of a sustainable management system.