Breakspeare was born in Toronto, Canada, to a Jamaican father, Louis Breakspeare, who was a British-Jamaican of multiracial ancestry, and a White Canadian mother of British origin, Marguerite Cochrane. Cindy has three brothers and one sister. She moved to Jamaica when she was four years old, and attended the Immaculate Conception Preparatory School. As a teenager she participated in beauty pageants, including Miss Jamaica Body Beautiful and Miss Universe Bikini. She was invited to participate in the Miss World competition in 1976 held in London, and won the title on November 19, 1976, becoming the second Jamaican to do so.
Breakspeare had an infamous relationship with the iconic and legendary reggae musician Bob Marley. From their relationship she gave birth to a son, Damian Marley (aka Jr. Gong), in 1978. However, 3 years later she married senator and attorney Tom Tavares-Finson in 1981 with whom she has a son Christian (1982) and a daughter Leah (1986). Breakspeare and Tavares-Finson divorced in 1995.
She is currently married to musician Rupert Bent II. Breakspeare has been pursuing her career as a Recording Artist and Entrepreneur. She founded a Rastafarian craft store called "Ital Craft" in Jamaica. Breakspeare has four grandsons from her three children.