Wine tourism has gained significant attention as a promising form of alternative tourism, aligning with modern tourists’ preference for experiences and frequent but shorter trips. This research aims to identify motives for visiting wine destinations by examining critical factors influencing destination choice, overall satisfaction, tourist loyalty, and market segments. An online questionnaire was utilized in data collection, employing a non-probability sampling method, with a final sample of 266 wine tourists. Critical factors for choosing a wine tourism destination were “There should be enough information available about the destination and wineries”, “Wineries accept visitors” and “Wineries hold wine-tasting courses”. The highest rated motives for visiting a wine tourism destination were “To learn to recognize a good wine”, “To try local wines and associated local food” and “To learn how to purchase quality wines”. Tourists reported (on a 5-point Likert-type scale) that they tend to be satisfied with their chosen wine destination (MV = 3.82) and are likely to recommend it to other potential wine tourists (MV = 3.99). Data analysis extracted two critical factors in choosing a wine tourism destination, i.e., “Wine Route Prominence and Amenities” and “Information Availability and Visitor Access”. Additionally, factor analysis extracted three factors for tourists’ motives, namely “Wine knowledge”, “Experiential tourism” and “Socialization”. Cluster analysis identified three distinctive groups of wine tourists: the “Popular destination-orientated tourist”, the “Socializing-orientated tourist” and the “Don’t care but it was a good experience tourist”. These insights can help managers develop strategies to satisfy wine tourists in order to retain existing ones, fostering future loyalty, as well as attracting new ones.