Sensory properties are important elements to evaluate the qualities of vegetable products and are also determinant factors in purchasing decision. Here we report the Italian results of a preference mapping study conducted within a larger European project with the aim of describing the preferences of European consumers in regard to the diversity of traditional and modern tomato varieties, available on the market. This study has allowed the assessment of fruit quality at 3 levels: objective description of sensory properties, consumer preference tests, and physicochemical measurements. A set of 16 tomato cultivars, with different fruit sizes and shapes, was described and classified according to 18 sensory attributes including flavor, appearance, and texture characteristics. The same cultivars were evaluated by 179 consumers in a “preference mapping” experiment with the goal of identifying the preferred varieties and the reasons for the choice. The consumer data are referred to hedonic ratings (aspect liking and overall liking), familiarity for the analyzed cultivars, and individual features collected by a questionnaire. A hierarchical analysis of the clusters allowed to distinguish, within the sampled Italian consumers, 4 segments with different preferences which represented 19%, 25%, 41%, and 15% of the population, respectively. A partial least square regression model allowed the identification of the sensory attributes that best described consumer cluster preferences for tomato cultivars. Both texture and flavor descriptors were important drivers of consumer preferences, but the relevance (predictive value) of individual descriptors to model tomato liking was different for each consumer segment. Information on demographic and behavioral characteristics, usage habits, and factors relevant for purchasing were also provided on the 4 groups of consumers.