The literature contains scant information on the relationship between tourists’ gender and their attitudes toward food while vacationing. The present study had as its main aim to examine the role of gender in key behaviours concerning tourists’ food choices and eating habits; in addition, our study evaluated the hypothesis that gender interacts with the “pandemic effect” in modifying tourists’ food-related behaviour. By implementing a quantitative, exploratory, and descriptive methodology, an online questionnaire was developed based on existing literature. To this end, data derived from 474 female and 370 male tourists visiting Greece in 2019 (before) or in 2020 (during the COVID-19 pandemic) were analysed and evaluated. The results indicate that, compared to men, women were more motivated to taste local food, especially with respect to obtaining cultural experience and excitement, promoting interpersonal relations, and as a result of health concerns. In addition, they dined at facilities at their place of stay, as well as at Greek restaurants and taverns at a higher rate compared to men. Women also reported being more satisfied than men by their food experiences during their trips, and was found that during the pandemic they spent, on average, more on food than before. The study showed that the pandemic affected both genders; however, the most significant of the differences observed relates to the choice of dining facilities, in all likelihood, as a result of women being more sensitive to the risks of COVID-19. Overall, during the pandemic, women appeared more likely than men to adopt behaviours that are in line with the principles of sustainability, such as a positive attitude and motivation to consume foods produced locally in the country. Differences detected between genders can be used by various stakeholders as a benchmark to further improve the food services offered at tourist destinations.