At the age of six, wanting to become a singer, Stefano Bollani would accompany himself on the family keyboard. A few years later, he recorded a cassette of himself singing and playing, which he sent to his idol Renato Carosone, along with a letter explaining his dream. Carosone replied advising him to listen to a lot of blues and jazz, and so Bollani did.
His first record was the second volume of the jazz encyclopaedia published by Fratelli Fabbri. At age 11, he enrolled at the Luigi Cherubini Conservatory of Florence, where he received his diploma in piano in 1993.
At age 15, he tread the boards professionally, playing mostly pop, at the same time studying under Luca Flores, Mauro Grossi, and Franco D'Andrea whose seminars he attended at Siena Jazz.