During a recent episode, the 64-year old music icon spoke out about the difficult experience and its impact on her family.
Born in 1957, the "Turn the Beat Around” singer was just a few years prior to Fidel Castro's historical assumption of power in the island country.
Entertainment Tonight: She recalled that she left Cuba at the age of two-and-a-half years old. "In May 1960, I was brought to America by my father, a police officer in the Cuban government."
Estefan stated that her father returned home from work with troubling news the night Castro, who died in 2016, seized power.
He told Estefan's mother and wife, "We're in trouble. The president just left the country."
According to the songstress, her mother had urged her to not return to work as he would be arrested. But he insists that it was his duty to "protect the Cuban people."
Estefan's mother was right. Estefan's father was also jailed.
The actress from "Vivo" said that her father, a commander in army's army, and him were both jailed. He was released about three to four months later, and he informed my mother that he wanted to get me out of Cuba.
She said, "They knew who Fidel Castro is, what was coming. Castro attached himself to communism. My father fled Cuba and went to the U.S. with Pan Am airlines. I still have my roundtrip ticket."
Emilio Estefan (star's husband), also shared his story.
The producer, 68, said that Castro had come to my home looking for dollars when he was 11. They looked around, and then they went to the safe. My dad became nervous and couldn’t open the safe. They took down the entire wall and found nothing.
A few years later, his family was planning to leave the country. This was an emotionally charged time for the future musician.
"I wept leaving Cuba. But my mom told me, 'Don’t cry.'" My grandfather and uncles gave me an image and told me that they would never see me again. This was one of the most difficult things for me. They never saw me again."
The Estefans found a way to get Emilio and Lili's brother, several years later.
Gloria claims that Emilio left on a 20-foot boat called Popea. She said that the crew didn't know what they were doing and ran out gas. They spent 10 days at sea.
Emilio said that despite going days without food or water, and being accompanied by a pregnant wife back at home, the mission was worthwhile.
"You will know what you would do for your family when you have children in the future." He insisted that the only thing we do was try to save our family's life to be in a country free of criminals. He was informed that his family would not allow him to return home once he had arrived.
Six months later Gloria and Emilio received visas that allowed their family to assume responsibility.
Lili expressed her gratitude to Lili for letting him go, and for Emilio risking his life to save mine, my brother's, and my father's lives. I have worked so hard to make you guys proud of me. It was worth it, I want you to know.
Gloria stated that their efforts were not futile.
Emilio insisted, "It was my best life event."