In recent years the issue of touristification has been progressively discussed in relation to its impact on historic towns. In this regard, physical transformations and gentrification consequences are both issues often addressed. In Italy, consciousness on the subject primarily grew in relation to Florence and Venice, both national cases widely discussed also on newspapers. The awareness of a wider range of cases affected by this problem, from big cities to small holiday destinations, is even more recent. The aim of the present paper is to address Capri’s touristification process, which started in the last decades of the nineteenth century and exploded in the second half of the twentieth century, from the point of view of the field of study of history and conservation of cultural heritage and landscape. Therefore, this process and some of its consequences on the island’s cultural landscape and identity are thoroughly analyzed. The paper starts with a brief introduction to the island and its history, which is necessary in order to highlight its rich cultural heritage and the slow pace at which Capri has grown over time as a fishermen island to suddenly transforming into a touristic destination during the last century. Finally, the current touristic vocation and the consequences on Capri’s natural and built environment are discussed, with the aim of individuating if and why there have already been losses and what should be done to prevent this negative process from going on.