European long shelf-life (LSL) tomato landraces can be classified into two main groups: the Italian group, including ‘Piennolo’ landraces, and the Spanish group, including the ‘Penjar’ and ‘Ramellet’ landraces. In this study, a partially common set of ‘Piennolo’ and ‘Penjar-Ramellet’ varieties was grown in Italy and Spain to evaluate the effect of different agro-environmental and storage conditions on fruit quality and shelf-life. Overall, both Italian and Spanish LSL genotypes lost their peculiar phenotype in terms of physicochemical properties and shelf-life behavior when not grown in their original agro-environment. To better understand the sensory attributes that drive consumers’ preferences, all varieties were characterized using descriptive sensory analysis combined with hedonic tests. The evaluations were conducted postharvest on raw and processed products according to the country’s culinary tradition (baked in Italy; spread on bread in Spain). Sensory description by trained panels conducted on raw and processed products highlighted different sensory profiles between the two LSL tomato groups. In the ‘Piennolo’ group, a reduction in sensory diversity among the genotypes was observed in the baked products compared to the raw ones, while this trend was not observed for the ‘Penjar-Ramellet’ group. None of the varieties fully met the consumers’ preferences.