Olive farming is one of the most important occupations in Messenia, Greece. The region is considered the largest olive producer in the country and it is recognized as a Protected Designation of Origin (PDO) for Kalamata olive oil, which is considered extra fine. In response to the declining trend of organic olive farming in Greece, this study assesses to what extent organic olive farming in Messenia provides a financially and environmentally competitive alternative to conventional olive farming. In this study, 39 olive farmers (23 conventional and 16 organic) participated in interviews based on questionnaires. The results showed that organic olive farming is significantly more profitable than conventional farming, primarily because of a higher price for organic olive oil. Despite this, the majority of the conventional farmers perceived a low profit from organic farming as the main constraint to organic olive farming. All farmers agreed that organic olive farming contributed to a better environment, health and quality of olive oil. Organic farmers used fewer synthetic pesticides and fertilizers and applied more environmentally-friendly ground vegetation management techniques than conventional farmers. Overall, organic farming was found to provide a competitive and sustainable alternative to conventional olive farming in Messenia.