Florence Greenway is a 20-km cultural and ecological itinerary located in the Oltrarno area, a neighborhood south of the World Heritage site ‘Historic Centre of Florence’. The project aims at merging three already-existing itineraries passing through gardens and monuments belonging to different institutions and two World Heritage sites (‘Historic Centre of Florence’ and ‘Medici Villas and Gardens in Tuscany’). The project is enhanced by a series of physical and virtual information material, as well as actions aimed at the requalification and restoration of components of the itineraries. This unique journey constitutes a long-term solution to offer alternative routes centred on slow tourism, sustainability, the rediscovery of green urban areas, and the well-being of visitors. Furthermore, it enriches the relationship between the historic centre, its surrounding landscape and the external neighborhoods, raising awareness of their significance.