This research investigates current preferences in wine purchase patterns and factors that affect the online purchase of wine by Generation Y and older cohorts in the Republic of Serbia. Our research utilizes descriptive statistics, chi-squared tests, the Mann–Whitney nonparametric test, and binary logistic regression. The results indicate that wine purchasing is conducted on an occasional basis—mostly monthly and weekly—with a tendency to buy wine throughout the whole year. The older cohort has a more pronounced rank, compared to Generation Y, regarding WTP for wines with a specific geographical origin and local wines. Although Generation Y and the older cohort have no habit of buying wine online, the information on geographical origin represents the most important online information related to online purchase intention. The strongest influence on online wine purchasing among members of the older cohort is a link that connects producers with consumers to allow the latter to obtain additional information and send remarks, suggestions, and/or praise, as well as a link to the winemakers’ association website, and the very significant influence of female gender. The strongest influence on online wine purchasing in Generation Y is the information on geographical origin. Female gender and income are also very significant. As wine consumption in the Republic of Serbia is gradually increasing, a growing interest in online wine purchases is expected. Our findings can provide useful information for building profiles of online wine consumers, depending on age cohort.