The Olympic Games are the greatest global sports and cultural festival, and this is why many cities in countries having a strong economy wish to host them, submitting to the International Olympic Committee (IOC) ambitious competitive programmes involving both sports and culture. The purpose of this study is to present in detail the programme of the Cultural Olympiad, which had a duration of approximately four years, to provide valid data for the evaluation of cultural projects and events, and to point out the impact of this great festival as an intellectual long-term investment and a tangible and an intangible legacy for the future development of the city. At the same time, the study will determine ways for managing and promoting the Cultural Olympiad, will define the meaning of the term "legacy", and will proceed to evaluate the impact of the Cultural Olympiad on Greek society. The question I have often asked myself during this research was whether and, if so, to what extent, on the occasion of the Olympic Games, Greece took advantage of a "golden opportunity" or whether this has been another "lost chance".