Although hemp cultivation is increasingly perceived as a promising option in terms of crop diversification, especially in semi-arid conditions such as in the Mediterranean region, its adoption remains limited thus constraining the development of hemp value chains at a larger scale. Our objective was to explore suitable conditions, at farm and downstream levels, for organic hempseed oil production in Sicily, taking on an action-research perspective that involves local actors. Based on a preliminary characterisation of barriers to organic hemp development at different value chain levels, we carried out targeted complementary investigation: (i) assessment on agroenvironmental performances of integrating hemp in durum wheat-based rotations; (ii) chemical analysis of local hempseed oil; (iii) exploration of marketing opportunities and value chain development. Our results showed that the lack of technical and economic knowledge as well as the deficiencies of suitable cultivars and adequate machinery were the main barriers for the organic hemp value chain development in Sicily. The analysis of agroenvironmental performances also revealed both strengths and weaknesses of hemp introduction in durum-wheat based rotations. Despite the identified limitations, we demonstrated that the organic hemp value chains represent interesting perspectives for the Sicilian farming sector, particularly in case of substantial barriers removal or adaptation.