Caridi began his career playing for minor Tuscan club Pontedera. He made his debut with the then-Serie C2 club in 1999, aged 19, playing 22 matches and scoring four goals. He then earned a move to promotion chasing Serie C1 side Alzano Virescit, where he made 15 appearances before being loaned to Avellino on January 2001. With the biancoverdi, he played 10 matches scoring three goals before returning at Alzano.
After 15 league matches played for Alzano in the first half of the 2001-02 season, he was signed by Serie C2 side Mantova in January 2002 after suggestion by then-head coach Roberto Boninsegna.
The 2002-03 season proved to be a turning point for the 22-year old Caridi. Indeed, he agreed to sign for free with Mantova and proved instrumental to make telling passes as Mantova came close to promotion. In 2003-04 Caridi made 32 appearances, scoring 8 goals as Mantova earned promotion to Serie C1.
In 2004-05 Mantova earned promotion to Serie B at their first attempt, with Caridi helping to create many of the goals with his technique and vision, as well as scoring 10 goals. In their first season in Serie B Caridi was moved up as a deep lying striker, a role more similar to the likes of Gianfranco Zola. Mantova finish fourth, losing a third consecutive promotion on playoffs to Torino, and Caridi scored 14 league goals in the process. In 2006-07 Caridi confirmed his qualities, scoring an impressive 11 goals in 35 matches, many of them coming from direct free kicks.
During the 2010 summer transfer market he completed his move to tuscan Serie B team U.S. Grosseto.
He was nicknamed "Don Tano" by Mantova fans due to his Southern Italy origins.