Recently, there has been significant consumer demand for traditional tomato varieties due to their favourable organoleptic qualities; however, the cultivation of these ancient varieties is becoming more restricted due to inadequate shelf life and low productivity. The “Pisanello” is a Tuscany tomato variety mainly cultivated in the provinces of Pisa, Lucca, and Livorno, and the main producers of this ancient tomato are small local farmers. The purpose of this work was, firstly, to study the range of quality parameters of this landrace tomato grown using different cultivation techniques, both in soil and soilless systems. For this purpose, the physicochemical parameters of Pisanello tomatoes grown in six different farms in Tuscany using both soilless and soil methods were investigated. Secondly, Pisanello tomatoes grown using different soilless techniques (rockwool and aeroponics) and soil-grown tomatoes (Pisanello and Goldmar F1) were evaluated from organoleptic and nutraceutical points of view. The sensory profile evaluation of all types of tomatoes under investigation was carried out. The aeroponic cultivation of Pisanello induced higher organoleptic qualities than those of tomatoes cultivated in rockwool (+34% for titratable acidity and +18% for total soluble solids). On the other hand, soilless rockwool-grown tomatoes showed a better sensory profile with respect to aeroponic cultivation. Nevertheless, the Goldmar F1 tomato, morphologically similar to ‘Pisanello’, received lower scores from the sensory panel compared to the Tuscany landrace tomato. This indicates that ancient tomato varieties selected over decades remain the preferred choice for consumers. Therefore, from a long-term viewpoint, the valorisation of local tomato varieties such as Pisanello can promote the regional commercialization of novel niche products originating from ancient fruit thanks to their acceptability by consumers.