Caracciolo first football appearances were for Sancolombano of Italian Serie D (amateur league); later playing for Como and Pro Vercelli, both in professional leagues, before being signed by Brescia in June 2001, in co-ownership deal for lire 470 million (€242,735).
Caracciolo made his Serie A debut on 6 January 2002, against Bologna. In June 2002, Brescia bought him outright.
During the 2002–03 Serie A season he played for Perugia, before returning to Brescia, scoring 12 goals at the end of the 2003–04 season.
After the relegation of Brescia, he was signed by Palermo on 1 July 2005, for €9 million., with €3 million being converted to the signing of Davide Possanzini. He soon became Luca Toni's replacement, who left for Fiorentina. In the 2005–06 season, Caracciolo played 35 games, scoring 9 goals. In the next season, Caracciolo has limited chance since the arrival of Amauri and David Di Michele. He scored only 5 goals in 27 matches, and made 17 starts.
In June 2007 was sold to Sampdoria in a co-ownership bid, for €4.25 million. as their centre forward Emiliano Bonazzoli is recovering from injury, Francesco Flachi, Fabio Bazzani and Fabio Quagliarella all left the club. That month also saw Caracciolo replaced Quagliarella, Quagliarella replaced Vincenzo Iaquinta and Fabrizio Miccoli replaced Caracciolo. Moreover, Sampdoria and Palermo formed numbers of swap deal in 2006 summer transfer windows, made there was a net debt of about €2.2 million from Palermo to Sampdoria on 30 June 2007 (without counting Caracciolo; or exactly €3.5 million ca in July 2006);, made the signing of Caracciolo again involved little cash.
He faced competition with Claudio Bellucci, Antonio Cassano and fit again Bonazzoli, which he made only 6 starts.
On 31 January 2008 Caracciolo agreed to return to Brescia in a permanent transfer, for €7.05 million, with Sampdoria received half of the transfer fee (€3.55 million) Yet, instead of receiving cash, Sampdoria signed Morris Donati and Mattia Mustacchio in co-ownership deal for €300,000 and €700,000 respectively and rested of the credit was used for signing Marius Stankevičius (€3M) in early July.
In 2011–12 Serie A, Caracciolo had half his rights bought by Genoa C.F.C. for €1.5 million in another co-ownership deal, which the club was searching for a reliable centre forward for years; Genoa also failed to sign Antonio Floro Flores early in June and sell Sergio Floccari after the expire of loan. Caracciolo also re-joined former Como owner Enrico Preziosi, who signed former players of Genoa or Como in recent seasons, likes Abdoulay Konko (January 2011), Cesare Bovo (2011). However Caracciolo failed to meet the demand of the management team.Novara
In January 2012 Genoa signed Italian internationals Alberto Gilardino and Rodrigo Palacio was recovered. It made Caracciolo no room in starting eleven. Caracciolo was loaned to Serie A struggler Novara (18th at that time), replacing the left of Riccardo Meggiorini. He scored his first goal on 12 February, marking the winner in a 1–0 shock exploit at Stadio San Siro against Inter.
In June 2012, Genoa sold back the 50% registration rights back to Brescia for €200,000.
Caracciolo became a member of Brescia in 2012–13 Serie B. On 22 November 2014, he scored a hat-trick of penalties in a 3–3 home draw against Carpi, match valid for 15th week of 2014–15 Serie B.
Caracciolo played for the Italy U-21 team, with whom he won a European U-21 Championship in 2004. He also earned a call-up to the 2002 squad.
In November 2004, he made his debut for the Italian national team in a friendly match against Finland.
On 16 August 2006 he was recalled to the Azzurri squad by new coach Roberto Donadoni for a friendly game against Croatia, replacing Cristiano Lucarelli in 65th minute.