Some came for love. Others to flee the reach of US justice. Then there were those seeking Utopia.
Susan Hurlich's pilgrimage blended the three, and now she is one of an estimated 2,000 to 3,000 Americans living in Cuba, according to officials at the US Interests Section, the Havana office that acts in place of an embassy. US-Cuba diplomatic relations were broken in 1961.
That number, a tiny fraction of Cuba's 11 million people, is remarkably low, considering only 90 miles separate the countries. Most US citizens here, however, are the children of Cuban parents who were living in the United States when they were born.
Americans born to American parents - such as Ms. Hurlich - are much fewer in number.
"I was embarrassed to be an American," says Hurlich, a self-described "anthropological journalist," who today navigates Cuba's potholed streets on a Chinese Flying Pigeon bicycle. "I knew there had to be a more human, equal, and just system."
The Boston native began her journey to the Marxist state before meeting her Cuban husband, and before joining Cuban Ernesto "Che" Guevara's brigade to build hospitals in Angola, the island's war-torn African ally.
A devout Communist, she fled her home in Berkeley, Calif., in 1969 to help her boyfriend escape the draft for the Vietnam War. She has promised never to live again in the United States.
Officials at the Interests Section say US expatriates here steer clear of their nation's authorities.
While the law does not explicitly prohibit Americans from living in Cuba, the Trading With the Enemy Act bans US citizens from spending money in Cuba. A select few are permitted to visit.
"There's no organization, so it's hard to know exact numbers," says a US official.
Before fizzling out in the 1980s, there was an organized group of Americans. The nearly 30 expatriates, some members of the US Communist Party, others leftist writers or English teachers, called themselves the Union of North American Residents. On May 1 - International Workers Day - they would march in Havana parades.
"The one thing we all had in common was our respect and unbridled admiration for Fidel Castro," wrote William Lee Brent, a former member of the Black Panther Party, in his autobiography, "Long Time Gone."
About 90 US fugitives live under the diplomatic aegis of Cuba. They include Robert Vesco, an American financier indicted for illegal cash contributions of $250,000 to President Richard Nixon's 1972 campaign.
Their future may hinge on the conflict between Fidel Castro's Communist government and the United States. A reconciliation between the two countries, which have no extradition treaties, could allow a federal marshal to escort them to an US prison.
Some expatriates, however, know they'll never go back. Lorna Burdsall, a grandmother who has lived in Cuba since before the revolution, has too much invested in the tropical island. The septuagenarian daughter of a wealthy Connecticut doctor quit a fellowship as a dance student at New York's Juilliard School in 1955 and boarded a plane with her new husband to an island she had never visited.
Her husband, Manuel Pineiro, went from being a Columbia University business student to become Cuba's top spy for more than 30 years. Though Ms. Burdsall and Mr. Pineiro were divorced more than 20 years ago, she continued to raise her children on the tropical island, and eventually became the director of Cuba's Modern Dance Company.
"Cuba is my home," she says. "This is where my life is."
Hurlich, who has lived with her husband in Cuba since 1992, says she too is likely settled here for good, but she frequently returns to the States.
"I have a lot of friends that I miss, and that makes it hard," she says.
Inside Hurlich's apartment in the capital's once-exclusive Miramar district, paint is peeling off walls and an old Soviet TV flickers with an afternoon soap opera.
Hurlich recounts the positives of life in Cuba - the relative lack of violence, free medical care, and a strong community of caring people. Then she is reminded of the daily struggles of living in an economically devastated country.
"This is not the United States," she says. "Things are done differently. You can't think of what you lack by being here; you always gain something living abroad."