The alignment of food systems with the Sustainable Development Goals (SDGs) is generally envisaged to make a positive impact on sustainability. This paper outlines some critical environmental and socio-economic indicators for Sicily in order to compare and explore the outcomes of two juxtaposing key drivers in a scenario planning exercise, where the extremities are Industrial versus Regenerative Agriculture/Agroecology and a Proactive versus Reactive government response. The most rational and less risky scenario becomes the most sensible sustainable development option, around which a 2030 vision is projected for a bioregional sustainable food system for Sicily, which is aligned with the SDGs and related policies. To accomplish the 2030 vision, a holistic education-led developmental approach is outlined with a supporting bioregional strategic framework, whose key milestone deliverables are projected through a backcasting process. This paper therefore highlights the importance of consistency and alignment of a development vision with its strategic framework and ensuing implementation, failing which, the holistic bioregional approach is compromised by activities that are shown to negatively impact environmental and socio-economic indicators. For this reason, all public and private sector development plans and associated resources ought to be aligned with a bioregional strategic plan for a sustainable food system for Sicily.