This research has investigated Italian consumers’ preferences for and purchasing behaviors of strawberries utilizing the Best–Worst Scaling methodology (BWS). This approach enables the key factors that influence strawberry purchasing decisions to be identified and different choice groups to be characterized. To achieve this goal, a survey was conducted on a sample of 496 respondents living in the metropolitan area of Milan (North Italy). The declared preferences of the individuals for 12 strawberry characteristics, divided into intrinsic, extrinsic, and credence attributes, were first measured. A Latent Class Analysis (LCA) was then performed to identify different clusters of consumers according to the individuals’ preferences. Subsequently, the heterogeneity of the clusters was tested, using the Chi-square test, and sociodemographic characteristics and purchasing habits were considered. The results suggest that the most important attribute in the choice of strawberries was appearance, highlighting the importance of preserving it throughout the supply chain, followed by one of the increasingly important aspects of diets, which is health benefits. The attribute considered the least important was the brand. This study demonstrates, from a holistic point of view, that sociodemographic characteristics, food habits, and perceptions of different strawberry attributes influence consumers’ preferences and behaviors. Practical implications suggest a new prospective for communication marketing strategies for producers, creating a better brand identity and highlighting in their marketing all of the aspects that consumers would like to know about the fruits they choose as quality certifications.