Despite the agro-food sustainability issues have been developed and strengthened considerably for a long time, from an operational point of view the sustainable agriculture is still evolving and improvements of production systems are increasingly required to move farmers toward the implementation of agricultural practices environmental friendly and economically viable. Therefore, the evaluation of the economic sustainability becomes a key prerequisite to carry out business operations, while the environmental sustainability assessment can be a strategic tool also to increase the value of product and to structure green- oriented marketing strategies. In this sense, the development of innovative approaches for a systemic and integrated assessment of the sustainability represents an ambitious goal to pursue for scientists, practitioners and for the overall society. In this study, Life Cycle Assessment (LCA) and Life Cycle Costing (LCC) were applied to evaluate, jointly, the environmental and economic sustainability of different vineyard production scenarios in a PDO (Protected Designation Origin) wine-growing area in southern Italy. Two cropping systems (organic and conventional) and two training systems (espalier and gobelet) have been analysed. According to ISO norms 14040 (ISO, 2006a) and 14044 (ISO, 2006b), the study was carried out firstly defining goal and scope of the analysis and, then, considering as “functional unit” 1 ha of planted surface and as system boundaries the agricultural production phases “from cradle to gate”, or rather from plantation to wine grapes harvesting, excluding wine processing, distribution and consumption. The considered life cycle goes from vineyard plantation to disposal (25 y). The same life cycle, as well as the same parameters were considered for the LCC methodology by realizing in this way an inventory of costs complementary to LCA inventory data by adding to the analysis also other costs as farm labour remuneration, land and working capital. The results allowed to ranking the sustainability performances of different wine-growing scenarios.