This article investigates the scopes of naturist and anarchist discourses and practices, unraveling the points of encounter and disagreement between two projects of individual and collective transformation that put into practice a new way of understanding medicine and sanitary, promoting “healthy” and “rational” lifestyles. For this purpose, the historical development of naturism in Chile is studied in order to understand its philosophical bases and its perspectives on medical practices, to connect from this field its confluences with the anarchist movement, within which emerged expressions of the so-called “libertarian naturism”.