Sweet Mobility—“System to promote Walking for Elderly Empowering Tourism and improve MOBILITY” is a project co-funded by the European Union and the Tuscany Region, whose purpose is to spur cultural-tourist activities and thus mobility also by the elderly and frail users. The project aims at developing a technological system through a smartphone based on a simple and user-friendly interface and a non-invasive wearable device specifically designed in order to detect vital parameters to be monitored during physical effort resulting from simple activities, such as a walking. This system allows to provide the elderly or frail users with a safe guide throughout specific chosen walking paths or tourist places, by pointing out, in the meanwhile, all of the difficult parts of the pathway, the possible presence of unevenness, architectural barriers, resting facilities areas or points of particular and unique landscape relevance. It will be able to detect and signal hazardous situations in the distance as well and to provide prompt, remote or on-site, intervention. This project aims therefore at fostering mobility for the elderly, by removing physical obstacles and barriers that often prevent them to allow themselves recreational and tourist activities. The project and its goals, the development methodology and the planned experimentation stages are here in detail introduced.