The wine sector is paying more attention to sustainable wine production practices, but this topic is highly debated because organic viticulture aims to a reduction of environmental impacts, while conventional viticulture ensures an increase of yield. This work provides an economic and environmental comparison using different indicators whereas no previous studies on viticulture have faced on both aspects of sustainability. Two distinct vineyards within the same case study farm were considered, where conventional and organic viticulture practices were applied for 5 years. For each type of production, we calculated the economic benefit and environmental indicators such as the Water Footprint, Carbon Footprint, and an indicator of environmental performance associated with the vineyard phase (“Vineyard Management” or “Vigneto” indicator part of the Italian VIVA certification framework). This latter considers six sub-indicators investigating pesticides management, fertilizers management, organic matter content, soil compaction, soil erosion, and landscape quality. The multi criteria approach is a novel framework assessing sustainability on vineyard management using environmental indicators from VIVA calculator and the economic aspect. Main results showed that organic management in viticulture can be applied without having economic losses and with the benefit of better preserving the natural capital.