Notwithstanding the steady development of the international wine tourism industry, accurate relevant information and comparative surveys focusing on primary research appear inadequate in various wine-producing countries. Understanding the wine tourism market is vital for sustaining its further development. In addition to existing typologies for wine tourists, distinctions of winery visitors may provide a valuable tool to help wineries design and implement appropriate marketing tools. Accordingly, the aim of this study was to identify segment characteristics and variations among international and inland wine tourists based on a multinational sample of winery visitors in Greece; differences between experienced and inexperienced visitors, first-time and repeat visitors at a specific winery, individual and group visitors, and men and women were also examined. The empirical study was conducted at 18 wineries in the most significant wine-making areas in Greece, through 1,400 questionnaires forwarded to wineries for distribution among their customers through self-completion. The results confirm the existence of significant dissimilarities between domestic and international visitors in relation to pre-visit behaviour, primary knowledge and loyalty levels towards the winery’s brands, visitation motives, spending attitudes, income, age distribution, perception of the winery experience and future behavioural intentions. Differences among these groups were also identified. The practical implications of the findings are discussed to assist winery managers and other wine tourism stakeholders implement a more customer-centric approach and improve strategic planning.