Greenhouse tomato cultivation plays an important role in Sicily, being the primary production area in Italy, due to its favorable pedo-climatic conditions that permit extra-seasonal productions. In Sicily, more than half of greenhouse tomato production is derived from the Province of Ragusa on the southeastern coast, where especially cherry tomato typologies are cultivated. Over the last decade, the Ragusa Province has registered a decrease both in terms of greenhouse tomato area and harvested production due to several structural problems that would require restructuring of the tomato supply chain. Thus, since recognition of real costs and profitability of tomato growing is a vital issue, both from the perspective of the farm, as well as from that of the entrepreneur, the aim of this paper was to analyze the economic sustainability of Sicilian greenhouse cherry tomato cultivated in the Ragusa Province. In particular, an economic analysis on 30 representative farms was conducted in order to estimate production costs and profits of greenhouse cherry tomato. According to our results, the lack of commercial organization, which characterizes the small farms we surveyed, determines low contractual power for farmers and, consequently, low profitability.