How does the circular economy contribute to the sustainable development of the wine sector? What benefits and limitations can come from the application of the “10Rs”, the circular strategies theorized in 2017 and today a valid tool for the orientation and evaluation of sustainable business models? Through the analysis of 10 case studies (relevant to Northwest Italy), the research confronts a sector of great importance for Italy, the world’s leading wine exporter and second-largest producer. Through the systemic approach, which reads the systems of relationships between matter, energy, information, living beings, inorganic units, and other systems, the 10Rs become filters for a critical reading of winemaking and the post-use phases of wine when the producer’s responsibility meets that of the consumer. A number of relevant issues emerge, in terms of the negative socio-environmental impact of the supply chain; the case studies try to describe them and present a possible ethical and critical response. Although it emerges that the actions of circular economy practitioners focus on the valuing of by-products and waste from the supply chain, rather than on measures to minimize the amount of resources used, extend the life of goods, and reduce waste, the case studies help to broaden this “narrow” view of the circular economy.