In the mid-1960s, young Russian artists from Moscow and the cities of Vladivostok and Ussuriysk in Primorsky Krai formed the Shikotan Group, named after the island where they summered for months at a time and created thousands of landscape paintings. Their activities lasted until 1991, when the group disappeared soon after the demise of the communist regime. The area including Shikotan Island forms the southern Kuril Islands in the Okhotsk Sea. Fascinated with the wilderness of Shikotan’s picturesque sea coasts, rolling hills and beauty of young women-workers of the largest fish factory in the Far East of Russia, the artists represented Shikotan’s landscape idyllically, with a tranquil bay and a distinctive form of a double volcano. A particular composition (for example, Oleg Loshakov’s Shikotan, the Bay of Malokuril’skoe) comprising a bay in the middle plane and a distant view of the volcanic Mt. Tyatya on Kunashir Island, recalls views of Naples, an unmissable stop on the Grand Tours of Europe, especially for nineteenth-century Russian artists eager to work abroad. This paper intends to reconstruct the Shikotan Group’s activities based on field research and interviews with the artists, including the group’s leader, Oleg Loshakov. Further, it aims to describe the characteristics of the style of their paintings, which can be well-illustrated by comparing with the so-called “Soviet Impressionist Paintings,” a recently-coined definition, favored especially by American collectors.