The chapter argues on waterfronts transformation along rivers is likely to attract people and create 'active' places for health and well-being. Waterfront projects seek to create vibrant public open spaces for sociability and physical activity. So, health has to be considered by local authorities into the planning process in order to defend common goods. On the other hand, shared responsibilities among professionals and local people can help to better understand spatial dynamics, place and form. To this end the following questions should be raised: How to create a common vision for the regeneration of riverfront space? How to develop proposals with community engagement and acceptance? How urban design criteria can optimize accessibility to the riverfront? How to create a ‘greening’ strategy to be used for a 'well-being strategy'.The aim of this contribution is to show the potentiality of the River Arno in Florence that can effectively maximize recreational potentiality for well-being and health. Riverfront proposals for change with the creation of new open spaces for health such as parks, gym spaces, urban farming, and so on could be a great challenge for future urban design.