The olive oil quality, nutritional and sensorial characteristics are associated with the chemical composition, which is the result of a complex interaction between several environmental, agronomical and technological factors. The aim of the present study is to investigate the impact of the geographical origin, harvesting time and processing system on the chemical composition and sensorial characteristics of olive oils produced from the Lebanese olive ‘Baladi’. Samples (n = 108) were collected from North and South Lebanon, at three different harvesting times and from four processing systems. Results showed a strong effect of origin, processing system and harvest time on oil quality, fatty acid composition, total phenols and OSI. The early harvest showed higher total phenols content (220.02 mg GAE/Kg) and higher OSI (9.19 h). Moreover, samples obtained from sinolea and 3-phases recorded the lowest free acidity (0.36% and 0.64%), and the highest OSI (9.87 and 9.84 h). Consumers were not unanimous regarding the studied factors, although samples recording high ranks were mostly from South using sinolea, 3-phases and press systems at early and intermediate harvest. The overall findings suggest that the selection of the harvesting time and of the processing system could have significant influence on the characteristics of the olive oil.