Agriculture, and the related food systems, represents one of the sectors that use most of the available water resources and is responsible for a large part of the greenhouse gases increase in Earth’s atmosphere. The aim of the present research was to estimate the three dimensions of sustainability—identified by the 2030 Agenda—of the olive oil supply chain in a typical production area within Campania Region (South Italy), through the analysis of seven different olive oil systems: four certified as organic, two of which irrigated (BIO1, BIO2, BIO-IRR1, BIO-IRR2); two integrated (INT1, INT2); and one hobbyist (HOBB). The novelty of the research was the broad-spectrum sustainability evaluation of these systems, through the estimation of their water and carbon footprints, and some economic and social aspects, to classify them in sustainability classes. So, the Life Cycle Thinking approach was used to quantify the environmental impacts and the social issues, as well as the costs of production of 1 litre of packed oil produced. Environmental impacts were assessed thought the life cycle assessment methodology, with a focus on the global warming and the water footprint, using the SimaPro 9.0 software and Hoekstra methodology, respectively. The cost production evaluation was performed by the life cycle costing methodology, while a primordial approach of social sustainability estimation was built identifying the stakeholders involved and suitable impact categories. Results showed that, per litre of oil, HOBB and BIO2 were the systems that emitted less CO2 eq (0.73 and 1.50 kg, respectively); BIO-IRR1 and BIO1 were the systems with the smallest water footprint (2.97 and 3.65 m3, respectively); HOBB and BIO1 were the systems with the lowest production costs (3.11 and 3.87 €, respectively). From a social point of view, INT1 and INT2 were the most pro-social systems. Overall, BIO1 was in absolute the most sustainable system under the various aspects considered. Hence the need to spread more and more (a) organic production methods, characterized by the use of self-produced fertilizers (on-farm compost); (b) more efficient machines use, for saving fuel; (c) balanced nitrogen fertilization to lower the water footprint.