Born in Seravezza, in the Province of Lucca, Rossi started playing football with Lucchese in Serie B, moving for the 1998–99 campaign to Salernitana, newly promoted to Serie A. After two seasons he joined A.C. Fiorentina (for 17 billion lire; €8.78 million in cash plus player deal) and returned to the top division, remaining in Florence for two years.