Alongside his brother Tommaso, Enrico Chieffi grew up sailing dinghies in the Mediterranean. The Chieffis made their mark in the two-man 470 Class, winning the Italian Championship in 1979, 1980 and 1982, the European Championship in 1980, and the World Championship in 1985. They finished fifth in the Los Angeles Olympics in 1984, and were sixth in Atlanta, twelve years later.