Several authors have shown that some tourism typologies—i.e., rural tourism, nature-based tourism, or creative tourism—have a more predominant role in attaining regional sustainability. In this regard, this paper explores the impacts of five pilot projects of creative tourism on the sustainable development of the insular Autonomous Region of the Azores. Through direct exploratory tools, such as interviews and site analyses, the present study enabled us to provide greater insight into creative tourism projects and their relevance to the development of an ultra-peripheral island region. As part of the CREATOUR AZORES Project, this study is based on five creative tourism pilot projects operating in the Azores, Portugal. As such, it is recommended that the regional government, local authorities, and other relevant actors and players in this region actively support and create strategies to strengthen these projects (and similar initiatives) once they not only contribute to regional development and destination promotion but also promote much-desired sustainable development—once these kinds of tourism, in theory, and practice, counteract the dire effects of mass tourism.