“Vesuviano” or “piennolo” tomato is among the most famous Italian small tomato landraces and is cultivated on the slopes of Vesuvio volcano (Southern Italy). The “piennolo” tomato is an interesting case with regard to its potential sustainability, as it is traditionally grown in water-deficit conditions with a low fertilizer input. Fruits with a high firmness and a thick skin can be stored for 3–4 months at room temperature (“long shelf-life” or LSL tomato) without postharvest fungicide applications. The aim of this research was to study the retention, changes in quality, and nutritional traits of “Vesuviano” tomatoes over 120 days of “natural” storage. The dry matter, soluble sugar, organic acids, volatile compounds, and carotenoid contents were evaluated at harvesting and in fruits stored for 40, 80, and 120 days. Slight decreases in dry matter content, soluble sugars, and sweetness index were found, while the organic acids levels remained relatively stable. Moreover, interesting increases in the concentrations of certain flavor volatiles, alcohols, aldehydes, and terpenes were detected. Regarding carotenoids, the total lycopene levels exhibited a 1.5-fold increase from harvest to 120 days. The unchanged lycopene cis-isomer levels and the β-carotene/total lycopene ratio is characteristic of relatively stable isomerization activity and indicated an optimal ripening pattern up until the end of the “natural” storage period. These results, which demonstrate good overall quality retention of this LSL tomato, represent a well-grounded reason to enhance the cultivation and marketing of this genetic resource, the fruits of which can be appreciated by consumers during the winter–early spring, when high-quality fresh tomatoes are not available on the markets.