In Italy, the wine supply chain is a cornerstone of the national agri-food system and a driving force for the entire economy. The aim of this study is to map the profile of Italian wine companies through the analysis of multiple case studies. The study focuses specifically on companies in the Marche region, investigating their features and supply chain, with a specific focus on product and system certification adopted, marketing policies implemented, and the businesses’ relationship with institutions. A total of 18 companies participated in the study. The primary data for the research was collected through semi-structured interviews lasting 1 h, based on an interview protocol. The results show that the supply chain for the wine sector is configured to be short, even when cooperatives act as an aggregator. The small size and limited financial resources make it particularly difficult to promote the wine outside its reference context, and there is a lack of a network strategy at the local level. Many companies consider organic certification a disadvantage since it tends to homologate production to the large wine industries, making the product’s naturalness, typicality, and craftsmanship disappear.