The paper discusses a recently concluded digital application aiming to enhance the cultural tourism of Piraeus, Athens’ historical city-harbor (Greece). Among the research objectives, was the use of Innovative tools for the management of important cultural heritage, archaeological & architectural, including sites and neoclassical listed buildings along the proposed itineraries. The findings of 2 years’ study were included in the virtual Piraeus Archwalks: an application for the Architecture in the city of Piraeus financed by Piraeus Municipality, supported by European Regional Development Fund (ESPA) and realized by Aikaterini Laskaridis Cultural Foundation in Piraeus, Greece. All historical data about the Urban evolution of Piraeus city focuses mainly in the nineteenth c. and partially in the first decades of the twentieth c.: the methodology applied has shared relevant information regarding the development of urban space presenting historical maps and archival plans, archaeological excavations, the urban interventions of the nineteenth c., as well as the latest transformations in the modern city, after numerous in situ architectural surveys, indicative of the cultural 19th c. Neoclassical inventory, enriched with notable registered buildings dated in the beginning of the 20th c. (Eclecticism period in European Architectural history) that the Piraeus city centre offers. Concluding, the project provides various cultural itineraries, creating opportunities for heritage sustainable tourism, evidencing the architectural inventory incorporated in the digital application.