This paper reports on the experience of the first Placetelling® training course in Santo Antão and Santiago, Cape Verde, promoted by Società Geografica Italiana and Fondazione Lelio e Lisli Basso. Placetelling® is a particular type of storytelling of places that promotes local development and helps to develop a sense of identity and belonging among the members of the community. Indeed, Placetelling® supports local communities to become directly engaged in the preservation of their common legacy in order to transmit it to coming generations. Tourism is the field where Placetelling® can best express its potential. This is particularly true for what concerns tourism to islands. The paper shows the first results of what we can define as a “maieutic reworking of local heritage” in Cape Verde, through the sharing of narrative and symbolic artifacts. Special attention will be dedicated to some crucial issues: The involvement of stakeholders through the lenses of empowerment, the discrepancies between how sense of identity is perceived by the locals and how it is communicated to tourists, and how and to what extent Placetelling® can change stakeholders’ awareness of their own cultural heritage.