The current urban regeneration projects must respect the peculiarity of social compactness that exist in a specific territory and that depend on the degree of relationship established between the inhabitants and the places in which they live. Especially in Italy, these peculiarity create an "urban identity" that is a very complex heritage: shared, peculiar, nourished by stories, characters, memories of places and which was built by a balanced and symbiotic society, aimed at product excellence and quality of life. The dynamic strength of this compactness has designed the appearance of cities with strong distinctive characteristics, signs of cultural authenticity. Today this force is projected from the urban center to the surrounding territories, while in the recent past it was in the opposite direction, that is from the surrounding territories to the center of the city. In this direction and thanks to the renewed productivity in the food and wine sector, in recent years some urban redevelopment projects in Tuscany have been very innovative: buildings integrated into the surrounding landscape, associated with innovative technologies and designed to respect the existing value. They are models of a successful attempt to preserve the territorial identity by integrating the past (buildings, streets, gardens, churches, etc.) with the recent past (industrial buildings, cellars, social housing, etc.). This work presents the results of the research in the identification of some "itineraries" within the Tuscan territory, to highlight the contribution of architecture and design to the maintenance of that ideal thread that links the best practices of the past with the cultural identity of the present.