Tavano started his professional career with
Pisa, before being sold to minor
Rondinella, then in
Serie C2. He then joined
Empoli, where he slowly established himself as one of the stars of the small
Tuscan team. During the January 2006 transfer window, several Italian football pundits claimed that
Real Madrid were interested in signing Tavano,
 but he eventually signed for
Valencia in mid-2006, for €9 million.
 He received a call-up from the
in April 2006,
 when manager
Marcello Lippi held trails for the 23-man squad that would go on to win the
2006 FIFA World Cup, but he never made his international debut.
His time in Spain, however, proved to be unsuccessful, as he fell out with coaching staff after making statements in the press which led to him being a sub player for the majority of his short stay in Spain. Tavano then returned to Italy for a loan spell with
Roma, where he mostly served as a reserve player for the main giallorossi strikers, although he was able to win the
2006–07 Coppa Italia with the club.
In 2007, he was permanently signed by
 for a reported €5.5 million on a 4-year contract.
 He received the
, previously retired in honour of
Igor Protti and unretired that year under explicit request from the former amaranto star. Despite being the club top scorer in his comeback season in Tuscany, his side did not manage to escape from relegation. Tavano agreed to stay at Livorno also in their
2008–09 Serie B campaign in order to try to lead his team back into the top flight.
He scored a hat-trick against Avellino on the opening day of the season, making it the first round 1 hat-trick since 1994. He would then score at Piacenza, before standing back to back with a teammate in celebration. He missed a penalty against his former club Empoli with the score tied at 1–1, before
Antonio Busce scored Empoli's winner. Tavano would, however, get a goal in the 5–2 win over Frosinone, on the way to 25 for the season, giving him the
capocannoniere title, and ensuring promotion through the playoffs after missing out on automatic promotion to Bari and Parma. However, he had a hard season in Serie A, as Livorno were the only newly promoted team to go down. He scored the winner at Roma, but only scored 4 other goals. He was also inconsistent, so much so that one fan interrupted training to slap him. He was still described as important. New manager Giuseppe Pillon said, "He is a fundamental player but must be motivated. I believe he has a desire for revenge after a poor Serie A Season."