The current food system in the Val di Merse region of Tuscany reflects the growing commodification of food produced, moving toward single export crops such as grapes and olives rather than the historically more diverse crops. Land cover analyses revealed that although much of this rural landscape was abandoned in the later half of the twentieth century, farmland and woodlands still dominate the landscape. These lands might return to the intensely productive state that they were farmed under for thousands of years. However, in order for local agriculture to again become a reality in the Val di Merse region, the participants of the food system must work together to identify the obstacles to local agriculture and opportunities for bridging the gaps within the system.