Tourism-dependent countries like Cyprus, have been seriously affected by the shockwave that COVID-19 pandemic has generated to their sociocultural/economic fabric. One of the industries of Cyprus impacted is the wine industry. Indeed, the consequences of the pandemic have been reflected on various angles of the island’s wineries; from the day-to-day operations to their overall strategy. Moreover, they influenced their relationship to tourism and the provision of wine tourist experiences. This is even more apparent in the case of small wineries. In this respect, the paper examines how tourism related wine enterprises, and more specifically, small wineries in Cyprus, handled the crisis and its impacts, through the analysis of the wine entrepreneurs’ views. This study explores the dimensions of the pandemic imprinted on wineries’ business and highlights the pertinent measures taken to deal with them. Additionally, it illustrates how wine tourist activities have been affected, enhanced, and reformed for the smooth wine tourist experience to be provided. To do so, exploratory research was utilized to collect data through secondary sources and face-to-face in-depth interviews with winemakers/managers/owners of small wineries in Cyprus. Findings reveal that the greatest challenge that small wineries faced, was the high degree of uncertainty, as Hotels, Restaurants, and Catering companies (HO.RE.CA.) were temporarily closed and consequently, the wine consumption related to tourist flows was reduced. Small wineries took a series of measures to handle the crisis, such as emphasizing communications through online media, improving the provided -tourist- experience in the wineries, or enhancement of direct marketing and distribution strategies. The paper concludes with recommendations for small winemakers to deal with the shocks of crises and for their sustainable competitive advantage.