Drawing upon a comparative case study of organic and conventional farming in Western Greece, the aim of this study is threefold: firstly, to explore the organic and conventional farmers’ profile through a factor analysis. Secondly, to assess the economic viability of organic cultivation with respect to profitability and risk behaviour, through a Monte Carlo stochastic simulation model. Thirdly, to discuss the necessity for additional income insurance schemes. Research findings indicate that the organic cropping system currently stands out as the most economically viable alternative under the assumption of the existing payments; without payments, however, conventional agriculture would be preferred by all farmers, regardless of their degree of risk aversion