The significance of sport as a social practice remains hidden at the margins of sociology. This article aims to highlight the social significance of sport by providing a sociological interpretation of the transformations of sailing in Czechoslovakia, and later in the Czech Republic, following the Velvet Revolution of 1989. These sport-related changes are understood to be consequences of wider socio-cultural, economic and political transformations. Drawing on ethnographic fieldwork of the Czech sailing movement, I argue that during Czechoslovakia's communist period, a time when sailing was labelled pejoratively as a `bourgeois sport', it actually experienced a `golden age' of enchantment. Based on Weber's concept of disenchantment and its subsequent developments in contemporary sociology, this article demonstrates how this earlier enchantment was jeopardized by disenchantment threats that occurred after 1989, and how sailing has once again been re-enchanted in the current period.