This work focuses on shifting conceptions of river flooding in the Italian city of Florence and explores how the Florentine community engaged with the unstable waters of the Arno River throughout time by focusing on the 14th, the 16th, and the 20th century. The intent of this research is to explore what reactions are possible in the face of water fluctuations that make landscapes unstable and undermine existing socio-economic configurations. Indirectly, such study contributes to the discussion on a present/future shaped by extreme water fluctuations which increasingly are affecting places across the planet because of climate change. Articulated in three sections, this speculative journey is structured around particular floods that are approached as entry points into the various arrangements of ideas, practices, and materialities that characterize the relationship between Florentines and locally flowing waters throughout time. Each section relies on descriptions that different authors make of the event and analyzes the implications of their stories in relation to concurrent legislation, economic activities, urban configurations, and conceptions of water nature and movements. Thus, by investigating events that occurred in Florence and that have been recorded in history under the category of “flood”, narratives articulated around water fluctuations are used to identify new strategies to conceptualize and manage the instability that characterize land-water arrangements in a period of climate change.