In this paper, we present the development of a virtual reality application, namely “Roots in Greek History” or RoGH, which provides the user with a unique experiential travel or transfer back in time to specific historical periods and historical places which are part of the Greek history and its cultural heritage. The tool is a multi-purpose one which is mainly addressed to tourists, teachers, or researchers. The users are facilitated in deriving historical data, challenged to connect with the past, and are invited to explore the history and the time period, archaeological ruins, and monuments of the past through virtual reality. In order to achieve this goal, the system exploits a dynamically designed and organised chronology, which can provide historical content for various places and cities in different times of their history. Users are given the freedom to choose “place” and “time” and consequently to have access to a variety of content (including 2D or 3D models, text, photos, multimedia, etc.), in an entertaining and educational procedure that creates a personalised information path and leads to empowering knowledge.