Virtual reality (VR) technologies offer a unique opportunity in “3D reconstruction” of cultural monuments and historical cities that do not longer exist or have been modified (partially or totally). Even though technological capabilities are growing fast, emphasis is mainly given on developing virtual museums and exhibitions, while archaeological places and excavations are following. The present paper presents two distinct approaches for 3D reconstruction of the historical city of Nafplio (Greece), by developing 3D models for buildings and monuments the way they used to be in the 19th century. The authors have used their professional and academic experience deriving from their participation in a European Commission co-funded project in the framework of the Partnership Agreement 2007–2013, which was implemented by the “V. Papantoniou” Peloponnesian Folklore Foundation (the project’s beneficiary) in Nafplio. The authors aim (a) to present the importance of reconstructing past cities and (b) to implement gaming technologies in cultural organizations as a means of achieve specific educational goals. Results point out the growing need for close cooperation between the cultural and academic worlds with 3D creators, and, moreover, reveal obstacles and opportunities in reconstructing historical cities and monuments.