He was born Michael Tivolis in 1470. In his early youth he traveled to Italy, where many scholars had fled to preserve Hellenic culture despite the fall of Constantinople. After completing his studies in Florence, he went to the Holy Mountain in 1507 and entered Vatopedi Monastery, where he received the name of Maximos. Ten years later he was sent to Russia in answer to a request of Grand Prince Basil Ivanovich, who sought someone to translate works of the Holy Fathers on the Psalter, as well as other Church books, into Slavonic. Maximos completed this work with such success that he was made to stay in Russia to correct the existing translations (from Greek to Slavonic) of the Scriptures and liturgical books, and to preach. His work aroused the jealousy of some native monks, and Maximos was falsely accused of plotting against the Prince. In 1525 he was condemned as a heretic by a church court and banished to the Monastery of Volokolamsk, where he lived as a prisoner, not only suffering cold and extreme physical privation but being denied Holy Communion and the use of books.

One day an angel appeared to him and said 'Have patience: You will be delivered from eternal torment by sufferings here below.' In thanks for this divine comfort, St Maximus wrote a canon to the Holy Spirit on the walls of his cell in charcoal, since he was denied the use of paper and pen. (This canon is sung on Pentecost Monday in some Russian and Serbian Monasteries). Six years later he was tried again and condemned to indefinite imprisonment in chains at a monastery in Tver. Happily, the Bishop of Tver supported him, and he was able to continue his theological work and carry on a large correspondence despite his confinement. He endured these grim conditions for twenty years. Toward the end of his life, he was finally freed by the Tsar in response to pleas on his behalf by the Patriarchs of Constantinople and Alexandria and the intervention of pious Russian nobles. He was received with honor in Moscow, and allowed to carry on his theological work at the Lavra. The Tsar Ivan IV came to honor him highly, partly because the Saint had foretold the death of the Tsar's son. When the Tsar called a Church Council to fight the doctrines of some who had brought the Calvinist heresy into Russia, he asked St Maximos to attend. Too old and weak to travel, the Saint sent a brilliant refutation of the heresy to the Council; this was his last written work. He reposed in peace in 1556, aged eighty-six. Not long after his death, he was glorified by the Church in Greece as a Holy Confessor and 'Enlightener of Russia.' In 1988 (!) he was added to the calendar of Saints by the Moscow Patriarchate.