From 1949 to 1961, Cherkassky lived with his mother in the south of France. He toured widely during these years, performing frequently on all continents.

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In 1961, following the death of his mother, he moved permanently to the White House Apartment Hotel in London.

A modest and shy man, Cherkassky avoided publicity. His lifelong passion was travel. He loved vacationing in exotic locations such as Thailand, Madagascar, Tunisia, Egypt, Turkey, Greece, or Australia. In 1987, the seventy-eight-year-old pianist undertook a day trip to the North Pole.

Cherkassky was noted for his eccentricities and his undeviating routines. For example, he insisted that his hotel rooms had to be equipped with a piano; he practiced exactly four hours a day throughout his entire life.

Cherkassky's homosexuality was widely known, especially among fellow pianists, but discreetly practiced. Elizabeth Carr, a personal friend as well as his biographer, quotes him as saying, "I want a woman inside a man's body." She also states that Cherkassky was sexually active well into his eighties.

However, Cherkassky's attempts at establishing long term-relationships failed, and he often complained of loneliness. His most intimate and long-lasting friendships were with women.

Cherkassky blamed his inability to develop meaningful and intimate relationships with other men on his demanding travel schedule, his inflexible personal habits, and his practicing routine. While it appears from Carr's biography that Cherkassky chose a solitary existence (even while enjoying an active sexual life), it is nevertheless hard to believe that he was not influenced by the social stigma against homosexuality in making such a decision.

According to Carr, Cherkassky suggested that his homosexuality was a result of his life-long fascination with the personality and artistry of Vladimir Horowitz.

She intimates that Cherkassky was not happy about his sexual orientation, but acknowledges that he was never embarrassed by it. He regarded his homosexuality as simply part of his personality. He did not hide it, nor did he ever publicize it. He evinced no interest in joining the gay social scene.

During the last decades of his life, Cherkassky was recognized as one of the world's greatest pianists.

In 1991, he performed his so-called "eightieth anniversary" concert at Carnegie Hall in New York City. In October 1992, he was selected by Wanda Toscanini-Horowitz to perform a memorial concert in honor of Vladimir Horowitz at the Steinway Hall in New York City.

Cherkassky's last appearance took place on November 9, 1995 in Prague. He performed Rachmaninoff's Third Piano Concerto with the Czech Philharmonic.

He died on December 27, 1995 in London.

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