Human–computer interaction, Artificial Intelligence, and the multilingualism of digital culture open up unexpected scenarios in the contemporary design of cultural spaces with the creation of artifacts in which the analogic and digital dimensions come together to enhance the experience. Sensors and devices track user movement in the real world and translate the inputs into commands through hand gestures, speech recognition, head movements, tangible interfaces, or a combination of these elements. Through theorical models, concepts and tools, the paper reports the evolution of “User Experience” applied to personalized enjoyment and use of cultural places. The functional-performance survey of tools and technologies for perception, narrative and augmented interaction revealed models that highlight the diversity and richness of tangible and intangible cultural heritage through new forms of interaction and knowledge transfer. In this direction, new technological tools make it possible to detect, track and evaluate the personalized user experience by processing or producing large amounts of data. Therefore, on one hand the paper explores the limitations dictated by data management and user privacy in using such systems and, on the other, it prefigures new scenarios for amplifying and personalizing the user experience.