Proposed paper provides a brief description of the project entitled “Digital Routes in Greek History’s Paths (RoGH)” which is part of the National Scope Action "RESEARCH-CREATE-INNOVATE" of the Operational Programme Competitiveness, Entrepreneurship and Innovation, co-funded by the Euro-pean Regional Development Fund (ERDF) and national resources, under the NSRF 2014-2020. The project’s aim was to develop Virtual Reality technologies as a mean to present historical information and cultural content, in order to enrich end – user’s experience. Current work presents challenges faced during project’s implementation and its main Virtual Reality models developed. Moreover, Virtual Reality technologies are directly linked to historical / cultural content as part of digitalization occurred under Industry 4.0 era.