He started his professional career as a singer in 1959, participating in the Santo Domingo television show La Hora del Moro, hosted by Rafael Solano and transmitted by Rahintel.
In 1965, Cáffaro continued his career with the hit song "En ruinas", written by Rafael Solano.
Later, he recorded a cover of the famous hit song: "Cada vez más".
Cáffaro became more widely known when he won the First Prize Award of the Festival de la Cancion Dominicana in 1968 with Rafael Solano's song "Por Amor".
Cáffaro subsequently performed concerts in Puerto Rico, Colombia, the United States, Venezuela, Spain, Curaçao, Aruba and Cuba.