The wine sector is going through a significant evolution dealing with the challenges of competition issues in international markets and with necessary commitments to sustainability improvement. In the wine supply chain, the agricultural phase represents a potential source of pollution and costs. From the farmers’ point of view, these contexts require them to be more attentive and find a compromise among environmental benefits, economic benefits, and costs linked to farming practices. This paper aims to make a sustainability assessment of different wine-growing scenarios located in Calabria (Southern Italy) that combines conflicting insights, i.e., environmental and economic ones, by applying Life Cycle Assessment (LCA) and Life Cycle Costing (LCC) to identify the main hotspots and select the alternative scenarios closest to the ideal solution through the VIKOR multicriteria method. In particular, the latter allowed us to obtain synthetic indices for a two-dimensional sustainability assessment. Conventional practices associated to the espalier training system represent the best compromise from both environmental and economic points of view, due to the higher yield per hectare. The choices regarding Functional Unit (FU) and indicators were shown to have a high influence on results.