Lozinskij, born and raised in Petersburg, is considered the outcast of the Petersburg society at the end of the 19th Century, whose upheavals, nonetheless, he reflects by mirroring all the tribulations left by a kind of romantic Sehnsucht. When travelling in search of the Immense, paths of melancholy are quite often trodden and nature becomes a mere setting for his poetic focus: reflection. Like many of his contemporaries, Lozinskij reckons that constitutive elements of this “setting” are perfectly reflected by the island of Capri, where the author stays in the years 1913-1914. The island’s realia, both folkloristic and imbued with melancholy, become functional pillars for Odinočestvo, “random notes” halfway between travel memoirs and an aesthetic essay on life. The paper aims at recalling the poetics and the artistic peculiarities of this Author. At the same time, the work sets itself the goal of highlighting the intimate connections the Author weaves with the island of Capri. The analysis of the images and flashes of everyday life demonstrates how Capri stops being a mere island and becomes an entire world, enriched with myths and legends. We propose an analysis of some passages from Odinočestvo and a few lyric poems, linked to the island of Capri, highlighting the contradictory and multifaceted literary refraction of the island as a symbolic image of Southern Italy, as well as a constitutive part of what determines the “toska po Italii” (nostalgia for Italy).