Recent literature has highlighted the importance of testing the sustainability performances of supply chains. Nevertheless, this field of research is still in its early stages, in particular with reference to short food supply chains (SFSCs). This research analyzed producers’ and consumers’ perception of the economic, social and environmental sustainability of two SFSCs of a specific quality of cheese (Parmigiano Reggiano PDO) placed in two different contexts: the first is a rural area in the Appennino Tosco-Emiliano National Park mountains and the second is a peri-urban area in Parma surroundings, both in Italy. The case study also analyzed the carbon emissions of shopping for Parmigiano Reggiano at dairy shops. Qualitative and quantitative methodologies were employed to achieve the aims of the present study. For producers in both areas, the SFSC is a successful strategy to sell a part of their output in their own outlets, gain reputation, reduce costs and at the same time increase their levels of self-esteem. Product quality is the biggest factor attracting consumers to the outlet; moreover, it is associated with trust in the producers and the idea of combining “leisure with pleasure”. However, the environmental impact of the consumers’ purchase activities is a drawback.