Purpose The primary aim of this research is to investigate and compare the satisfaction of Generations X and Y at the cellar door in an Old World (Douro Valley) and a New World wine region (Napa Valley), including an assessment of demographic and psychographic profiles. Education is also a key component in determining the impact on wine consumption behavior. Methodology/approach A quantitative survey was conducted in counties/municipalities surrounding Napa and Douro Valley wine regions in 2009 and in 2016. The survey in 2009 was followed by a visit to two wineries in each region. Two forms of analysis were undertaken: cross‐sectional (comparing Generations Y with X, in each region) and longitudinal (comparing Generation X, in 2009 with X in 2016, and Y respectively). Findings Word-of-mouth (WOM) is the primary means of finding out about wine brands. Millennials pay special attention to packaging (label) and alcohol content when purchasing wine. Both generations prefer sweet and semi-sweet tasting wines as well as a less structured cellar door visit. Education is an important component, where the informants showed appreciation for a tour of the wine production process. Research limitations There is considerable scope for continuing longitudinal research, including both quantitative and qualitative methods, with a larger sample size to explore the impacts of building consumer education tied to a ‘winescape’ experience.