In this paper, two World Heritage island destinations are compared, Gotland in the Baltic and Rapa Nui in the Pacific. Both islands deal with a growing number of tourists, which asks for rethinking of tourism development. As cultural heritage plays a major role in tourism for both destinations, it is especially important to look into sustainable cultural tourism development from the perspective of authenticity. The paper is based on a variety of materials and takes an innovative approach to methods through a student–staff collaboration. The data show that social acceptance of tourism by local communities on both islands could be achieved through the creation of authentic experiences. Furthermore, data show that it is rather potent to engage both locals and tourists in modernized authentic experiences. However, this can only be done if locals are empowered and are genuinely allowed to steer the development of tourism.