The history of urban food forestry is very recent and early projects represent highly valuable operational case studies to obtain precious information on challenges, best practices and results. The Picasso Food Forest represents the earliest documented case study of urban community food forest in Italy. By hosting several perennial woody plants, it provides ecosystem services typical of a tree system including making biodiverse fresh edible fruits, vegetables and herbaceous plant easily accessible to adults and children reconnecting them to healthy eating habits, food growing and the special experience of foraging and harvesting food directly from the plant in a nature-like setting. It has contributed to develop a neighborhood community, place attachment and meaning among the citizens that participate to its implementation or that simply attend the area. Compared to more traditional community gardens, the food forest provides a deeper interaction with the natural world and related benefits. This is achieved by exposing people to a greater understanding of ecological processes that are at the base of the food forest design and functioning, and to a more complex physical structure and biodiversity, more similar to wilderness, stimulating sense of wonder, exploration, curiosity and observation. The Picasso Food Forest represents a hotspot of biodiversity providing a plant and wildlife nursery and shelter, and a genetic bank by including several heritage and local varieties. The setting of a case study that provides inspiration for new analogous projects in Italy and Europe is one of the main achievements. The Picasso Food Forest successfully challenges issues such as biodiversity loss, community segregation, food insecurity, climate breakdown, unsustainable consumption and production systems and it provides a model to rethink not only how cities should be designed but also how we, as a species, shall provide for our needs and live on this planet.