The chapter aims at analyzing whether female entrepreneurs have some distinctive capacities than men in managing business within the Italian wine industry and if these skills are useful for the sustainability of their farms and the whole sector. After the sketch of the women situation in the Italian agriculture and in the wine sector, we have analyzed two case studies located in two wine regions, Tuscany and Sardinia, by having meetings and interviewing two wine women. The two regions are quite different for the general condition of winemaking and for the internationally perceived image. Furthermore, the two informants have different family histories and manage different dimensioned farms. Our findings are that these two female entrepreneurs, even starting from different general conditions, have been able to use their own leading capabilities in the improvement of business and in collective regional and national initiative of wine promotion. Basing economic decisions on formal and/or contextual training, they have introduced innovations in farming, winemaking, and marketing in a specific way. We can say they have been someway slower, less hasty, and even more effective than men in involving collaborators with a charismatic heading and attracting other entrepreneurs in doing business. The role of women in farming has been too long underrated by society and the policymakers, who, on the contrary, should provide more specific attentions to the female capacity to foster the sustainability of their own farms and the wine Italian industry.