ICT-based personalization in cultural heritage has been an important topic of research during the last twenty years. Personalization is used as a means to enhance the visitors’ experience of a cultural site. Little consideration has however been set on lifelong cultural experiences, i.e. engaging the public in culture beyond the visit of a single site and bridging multiple sites. Cultural sites differ leading to a diversity of needs that should be taken into account through a personalization approach. This paper presents a set of scenarios tailored to suit the needs of three different Cultural Heritage sites in different EU countries. These scenarios have been developed within the EU funded project TAG CLOUD that aims at leveraging existing technologies to support realistic lifelong engagement experiences with cultural heritage through personalized content and interaction.