In the past, cities have been designed for the movement of young and healthy people, but this has created discrimination in the use of means of transport based on age, gender, social status and health. Then, urban space, instead of promoting inclusion, became a place of inequality and social exclusion. New forms of urban design should start from the needs of the most fragile people to promote greater safety, accessibility to means of transport, and a more participatory decision-making process. The older population group (65+) is the one that has been growing the most in the last two decades, and for this reason it is essential to design friendlier urban spaces and transportation solutions, designed and conceived for their physical and psychological constraints. Focusing our approach on older people as a relevant fragile group, this also means that by solving the needs of the most fragile, everybody else’s needs would be met. Using bottom-up approaches, to promote the meeting between citizens and municipalities, more inclusive and sustainable urban planning and mobility programs can be triggered, some of which, such as “Tactical Urbanism”, have established themselves in major European cities thanks also to Art-driven processes. In recent years Milan has emerged as one of the most innovative pilot cities in the field of mobility and redevelopment, thanks to plans like the “PUMS”, “Piazze Aperte” (Open Streets), and “Just streets”. This study investigates their impact in Milan, showcasing two of the successful pilot experiments (one in the north, another in the south) where the impact of the tactical intervention was translated into permanent solutions made of stone pavements, wider sidewalks, introduction of trees and flower beds, benches, play areas, bicycle lanes and bike parking. Finaly, the more central “NoLo” district is brought to the spotlight for its social and cultural vibrancy and long gentrification process, where the mobility of fragile population groups, especially older people, is considered seeking solutions for a better public space for all citizens.