This paper deals with innovative fruition modalities of cultural heritage sites. Based on two ongoing experiments, four pillars are considered, that is, User Localization, Multimodal Interaction, User Understanding and Gamification. A survey of the existing literature regarding one or more issues related to the four pillars is proposed. It aims to put in evidence the exploitation of these contributions to cultural heritage. It is discussed how a cultural site can be enriched, extended and transformed into an intelligent multimodal environment in this perspective. This new augmented environment can focus on the visitor, analyze his activity and behavior, and make his experience more satisfying, fulfilling and unique. After an in-depth overview of the existing technologies and methodologies for the fruition of cultural interest sites, the two experiments are described in detail and the authors’ vision of the future is proposed.