In the olive production sector, which is increasingly expanding beyond the borders of the Mediterranean basin, harvesting is the most demanding phase, from both an economic and organisational point of view. Traditional olive orchards are still predominant, with centuries-old and large plants, and are characterised by the gradual ripening of drupes and irregular planting patterns. Even though the structural conversion of these olive orchards into more modern cultivations may be difficult owing to their historical, monumental, and landscaping importance, as well as the existing legal restrictions, supporting a “modernisation” process aimed at mechanising the main farming operations remains a priority. Technological innovation is, therefore, a primary objective for Mediterranean olive growing, as well as for the enhancement of its strengths. The present study aimed at assessing different olive harvesting sites, considering the technical, economic, and environmental aspects, to develop a better version of the “olive harvesting database”. The applied methodology, also called the “modular approach”, represents a useful tool to apply in unitary process assessment to obtain a comprehensive database of diverse agricultural operations. Eight olive harvesting systems were compared: six highly mechanised scenarios, one based on mechanical-aided harvesting, and the final one based on fully manual harvesting. The mechanised systems obtained a better performance in terms of working capacity, as only 3.5 h ha−1 were needed to harvest 12 t using a self-propelled trunk shaker. In addition, the economic results revealed that mechanical harvesting, diversely from manual or aided harvesting, is the only way to decrease production costs. From an environmental point of view, manual and mechanical-aided harvesting showed the best performance in terms of impact per hour. However, using the mass-based unit (1 kg of harvested olives), the results were the opposite and this could be very relevant for the ecoprofile of olive oil.