The Traditional Cultural Landscapes (TCLs) have been studied from different points of view since the pioneering work of Antrop (1997). The aim of this study is to analyze the TCLs from a bottom-up perspective, focussing on the internal organization of a number of farms and looking at technical and economical characteristics, and also at social and cultural aspects. The focus is on Traditional Cultural Vineyard Landscape (TCVL) because the viticulture sector is the one most integrated with the kind of tourism that is interested in quality food products associated with a specific place of origin, and also the sector that, more than others, has responded to market changes by increasing the appeal of their products. Accordingly, the economic performance of three Italian winemaking farms was analyzed by means of cost-based method to explore: the cost of restoring a TCVL; the cost of producing the grape and the wine; the economic profitability of the investment in the TCVL; the relationship between entrepreneurial strategies and the use of landscape in a functional perspective. The positive financial results achieved by these farms in different part of Italy suggest that the financial success or failure of an investment in landscape is not determined by the socio-economic context but by the ability of the farm to differentiate its product, gaining a competitive advantage by offering customers greater value. The key issue is not the contrast between those who support the costs of landscape preservation (vineyard owners) and those who reap its benefits (the community as a whole), but rather in the way in which the added value resulting from preservation of the landscape is being obtained and distributed. The results demonstrates that landscape preservation can be a driving force for improvements in farm management and farm income but it is still necessary enlarge the duty to contribute to their preservation improving government measures for the restoration and preservation of the TCLs, and consumer awareness about the importance of products from these areas with TCLs.