Plums are climacteric fruits with reduced shelf life and they represent a very appreciated product for fresh consumption. European consumers can find several plum cultivars that offer different organoleptic characteristics, flavor and aroma. In this study, chemical properties, such as total soluble solids (TSS), pH, titratable acidity, total phenolic and anthocyanin contents, aroma profile and sensory evaluation of seven plum cultivars were investigated. Significant differences in chemical properties were found in ‘Settembrine’ and ‘Angeleno’, the late ripening European plums that showed the highest TSS content and the lowest acidity values. As expected, a high level of anthocyanins was detected in red pulp and red flesh plums such as ‘Dofi Giudy’ and ‘Black Diamond’, though significant differences in their total phenolic amount were observed. ‘Dofi Giudy’, ‘Black Diamond’ and ‘Laroda’ showed the highest aroma profile among the investigated cultivars. Finally, a discrimination among the cultivars was obtained by combining the volatile profiles with a back-propagation neural network analysis (BPNN). The results showed that C6 compounds such as esters and aldehydes were strongly related to flavor perception of the panelists. ‘Dofi Giudy’ was the mostly appreciated plum due to its juiciness, sweetness and flavor intensity; furthermore, when compared to the other cultivars, it also showed remarkable levels of total soluble solids, total phenolic and anthocyanin contents.