Wine tourism and research surrounding it has developed substantially over the last 15 years. The importance for wineries of visitation to cellar doors is recognised by both the tourism and wine industries (Carlsen and Charters, 2006; Mitchell and Hall, 2006) and the need to understand the expectations and experiences of wine tourists has driven much of the research that has been conducted. Ensuring a match between expectations and experience of the cellar door will affect not only the tourists‟ satisfaction with the experience but their emotional attachments to the brand and, by implication, their future purchase intentions (Dodd and Bigotte, 1997). It is important to note, however, that wine tourists are not a homogeneous grouping (Charters and Ali-Knight, 2002; Mitchell, Hall, and McIntosh, 2000), and the importance of understanding the differences between them is increasingly recognised. Anecdotal evidence suggests that Baby Boomers, particularly males, have been viewed as the typical, and perhaps most desirable, wine tourist in the past (Charters and O'Neill, 2000). This is due to a range of factors, including their role in driving the growth in wine consumption in the Anglophone world, their perceived level of wine knowledge and wine involvement and greater disposable income. However, it is now becoming clear that a younger generation of wine consumers and wine tourists need to be considered if the industry is to have a long-term future (Koerber, 2000). This will require an understanding of the relationship of Generation Y to the winery experience. To this end, this chapter explores the attitudes, expectations and behaviour of Generation Y at the winery cellar door. In particular, the focus is on their preferences regarding the interaction they seek with cellar door staff, their needs with regards to the type of education and/or information sought during a winery visit and their overall attitude to a winery experience. The chapter is based on fieldwork conducted in Swan Valley, Western Australia, Yarra Valley, Victoria, and Waipara Valley, New Zealand. It is worth noting that Generation Y has been defined in this chapter as those born between 1978 and 1994 (Sheahan, 2005).