The present study investigates whether experiential learning through cultural promenades and ancient Greek drama can constitute an effective method of instilling cultural values in the new generation. For this reason, field research was conducted in the broader area of Acropolis in Athens, Greece. Qualitative research through in-depth interviews followed, in order to record 42 student teachers’ perceptions after their own experiential contact with the method of cultural promenades. This research method with teacher candidates during their vocational training as future teachers is of great importance, as it will indicate whether the method of instilling cultural values through cultural promenades and ancient Greek drama is effective enough to be adopted in later teacher candidates’ teaching in schools. The choice of the sample is strategic, since the teaching specialty of the majority is economics and management, and thus teachers get acquainted with an innovative experiential methodology on teaching economic and cultural sustainability, which—according to literature—are interconnected. The findings reported valuable insights on the effectiveness of the said teaching methodology. The present research is the first that focuses on the descriptive interrelations among cultural promenades, experiential learning, cultural values, and sustainability, and thus it provides policy makers and teachers with invaluable insights.