This review constitutes a comprehensive systematic review analyzing cultural routes, with a particular focus on the concept of the cultural route as a tourist–cultural product. Within this framework, the paper offers an overview of contemporary technological challenges, concerns, and limitations. It thoroughly explores cutting-edge technologies pertaining to the promotion of cultural heritage, both in general and in the specific context of realizing the concept of the cultural route, a tourist–cultural service enriched by the utilization of new media. Additionally, it extensively references the latest techniques and models for enhancing the user experience of digital cultural tourism products. Moreover, the paper showcases existing digital platforms and tools that encapsulate and emphasize the notion of cultural tourism. It assesses the respective methodologies, technologies, and techniques employed in each case, accompanied by illustrative instances of their applications. Finally, an empirical evaluation was conducted focusing on user needs and expectations during a cultural route.