Grigolo was born in Arezzo and raised in Rome. He began singing by the age of four. When he was nine years old he accompanied his mother to have her eyes tested and, hearing someone singing from another room, he spontaneously began his own rendition of "Ave Maria". The singer, the optician's father, was so impressed that he insisted Grigolo have an audition for the Sistine Chapel Choir as soon as possible. Young Vittorio was chosen to become part of Sistine Chapel Choir as a soloist. He then studied for five years at the Schola Puerorum at the Sistine Chapel. At age 13 he played the Pastorello in a performance of Tosca at Teatro dell'Opera di Roma, where he shared the stage with Luciano Pavarotti and was given the nickname 'Il Pavarottino'.  When 18, Vittorio joined the Vienna Opera Company. He became the youngest man to perform in Milan's La Scala at age 23.  He also raced Pre-3000 Formula cars for a while until an accident limited his opportunities in this field.