Simoni was born in Palù di Giovo, in Trentino, and began competing as an amateur with the goal of someday winning the Giro d'Italia. Simoni confirmed his potential in 1993, when he won both the amateur version of the Giro d'Italia (known as the Baby Giro) and the Italian Road Cycling Championship. Prior to his retirement in 2010, Simoni would reveal to the Italian newspaper "La Gazzetta dello Sport" that the Giro was the one race that attracted him to cycling and which motivated him as a professional. "It was the Giro that brought me to cycling when I was a child", he said. "It triggered my dreams."