Blind wine tasting refers to the practice of tasting a wine without seeing the label, and deducing the grape variety, location of origin, and vintage of the wine based on what one perceives and infers from the glass. We had the opportunity to analyse data from Oxford University Blind Tasting Society’s 2018 training season, where 15 participants attended 18 training sessions over 36 days. A total of 212 wines (104 white, 108 red) were tasted and a total of 2271 tasting notes were processed. The aim of this study was to assess whether blind tasting training can improve accuracy, both in terms of within-participant accuracy of guesses and wine structural elements, and in terms of group-wide accuracy (e.g. variance of guesses within a group). The results showed that over time, guesses for grape variety increased in terms of accuracy as well as within-group agreement. On the other hand, guesses for vintage decreased in terms of accuracy as well as within-group agreement. No change in accuracy was observed for place of origin (country and region) guesses. Moreover, it was demonstrated that for grape variety, country, region, and vintage, the chances of the most common within-group guess being correct was significantly higher than the underlying frequency distribution, e.g., if participants had just guessed the most frequently occurring grape/country/region/vintage. Structurally, participants’ estimation of acidity level increased in accuracy over time, while the average error in acidity and alcohol estimations were not statistically different from zero. Finally, we assessed how wine preference is related to wine attributes as well as the taster’s wine experience. It was demonstrated that, overall, wine preference was positive correlated with wine age, acidity, sweetness, and colour (red wine was preferred to white). Over time, we observed a shift in preference towards older wines, and a decrease in the importance of wine colour. Those with little initial blind tasting training also experienced a change in preference towards greater acidity and alcohol, and decreased their preference for oak. These observations have important implications for the acquisition of wine expertise, and for growing wine markets with an increasingly educated consumer population.