In some of their works, Maxim Gorky (1868-1936) and Mykhailo Kotsiubynsky (1864-1913) were inspired by their long stay in Capri. At that time, both authors were subjects of the Russian tsar, belonging to the same generation, and later became part of the Russian and Ukrainian literary canon, respectively. It was on the Italian island that they were able to meet and begin a friendship based on great mutual respect. In this article, after recounting the experience the two writers shared on the Italian island, I will analyze and compare excerpts from Gorky’s well-known Italian Tales (Skazki ob Italii) and Kotsiubynsky’s less famous The Dream (Son) and On the Island (Na ostrovi). More specifically, I would like to demonstrate how Gorky’s texts are more characterized by a realistic approach with social elements, while in the texts of Kotsiubynsky the details of the landscape fade into a literary impressionism with fairy-tale traits. However, in both cases the sunny island of Capri symbolizes the beginning of a completely new life (for the lyrical subject or even for the whole of humanity).