During the last decades, the wine industry has involved many regions competing with each other to gain market share and build their brand. In this sense, innovative marketing strategies have been used to improve their competitive advantage. The objective of this paper is to investigate the effect of digital marketing strategies in the wine industry, in the case of visitors at Northern Greece Wineries. The research also aims to explore wine tourists’ preferences and attitudes toward the digital presence of wineries, regarding wine tourism activities. For this purpose, a quantitative survey was conducted, using a structured questionnaire, distributed to a convenient sample of 193 visitors from twelve wineries in six regions of northern Greece, during their visits. Visitors were asked about attractive content on websites and social media, preferred types of online advertising, and desired features in wine tourism applications. In addition, specific online actions before their visit, such as booking methods, were investigated. The demographic profile and the type of visitors, the main reason for visiting the area, as well as future visit intentions, were also examined. The results showed that most wine tourists found the information they needed in the wineries’ digital media, and the wineries’ digital presence influenced several of them in their decision to visit the specific winery. Regarding social media, about one out of three visitors follow the winery’s page or account, with Instagram being the most popular, and wine events and relevant information being the most attractive content categories. Furthermore, social media followers showed more intention to revisit the winery in the future.