Italy was one of the seven participating countries to take part in the first contest in 1956 . The Eurovision Song Contest was initially inspired by the Italian Sanremo Music Festival , held annually since 1951 in the city of Sanremo . Since their debut Italy has taken part 37 times , and has won the contest twice - in 1964 with the song " Non ho l'età " ( I 'm not old enough ) performed by Gigliola Cinquetti , and in 1990 with " Insieme : 1992 " ( Together : 1992 ) performed by Toto Cutugno . Italy has also come 2nd once - again with Gigliola Cinquetti and the song " Sì " , and 3rd four times - including the global hit song " Nel blu dipinto di blu " , also known as " Volare " , performed by Domenico Modugno in 1958 . Italy has also hosted the contest twice - in 1965 in Naples , and in 1991 in Rome
Insieme : 1992
Insieme: 1992
Italy in the Eurovision Song Contest 2011