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Coram native goes to Cuba for ‘the best job in the world’

Chris Cloonan is seen in Havana, Cuba in

Chris Cloonan is seen in Havana, Cuba in this undated photo. Credit: AP Special for Newsday / Desmond Boylan

Chris Cloonan’s family and friends thought he was a little crazy when he decided to make Cuba the focus of his studies and his life. But he thinks he has “the best job in the world” on the Communist-run island, where he’s a tour guide.

Cloonan’s off-the-beaten-track venture is paying off. For the past year and a half, the Coram native and 2012 Stony Brook University graduate has worked in Cuba at the precise moment historic events have unfolded on the island. They include President Barack Obama re-establishing U.S. relations with Cuba, the Rolling Stones playing a concert in Havana and Fidel Castro’s death in December.

“When I first went down there, people thought I was nuts to do what I was doing because there had been 50 years of embargo and bad relations,” said Cloonan, 26. But “I love what I do.”

Cloonan’s job is to lead groups of tourists around an island that for decades was mostly off-limits to Americans because of a U.S. embargo. He accompanies artists, university and high school students, even baseball fanatics, to Cuba, where baseball — not soccer as is common on other Caribbean islands and throughout Latin America — is the national sport.

Cloonan was present for the Rolling Stones concert last March, and a baseball game between the Tampa Bay Rays and Cuba’s national team that Obama attended along with Cuba’s president, Raul Castro, Fidel’s brother.

His work has been made possible in part by Obama’s decision in December 2014 to restore relations between the two countries — located 90 miles apart — for the first time since shortly after Fidel Castro’s revolution triumphed on Jan. 1, 1959. In March 2016, Obama became the first U.S. president to visit Cuba in nearly a century, making for a Berlin Wall moment.

Americans can now travel to Cuba more easily and even on commercial flights, though still with some restrictions and often in need of a bilingual insider to show them around the island and explain a political and economic system that often seems alien to Americans raised in a capitalistic society.


Cloonan’s Cuba connection started at Stony Brook. Urged by his parents to study for a semester abroad, he went on a Stony Brook-sponsored expedition to Russia in July 2011. He didn’t care much for the former communist country.

But when Cloonan went on another trip in January 2012, this one to Cuba and run by Stony Brook’s journalism school, he was captivated. The weeklong journey during his junior year “totally changed my life,” Cloonan said.

He came back determined to delve into the topic of Cuba, and do what he could in his own small way to end the embargo, which he saw as a failed policy that hurts both countries.

Cloonan graduated from Stony Brook in December 2012 because of extra courses he had taken, and by the spring semester of 2013 enrolled in a master’s degree program in Cuban studies through Burlington College in Vermont that brought him back to the island.

He studied alongside Cubans at the state-run José Martí Institute in Havana. It was unusual for an American to be there. Cloonan is certain that Cuban spies were in the classroom watching him.

“I was just going to do it for a semester,” he said, “but I loved it so I kept doing it.”

After the semester, Cloonan visited as often as he could, and by December 2014 he graduated. It happened to be the same month Obama announced the re-establishment of relations.

“When the announcement came, I said, ‘See, I told you so. Now I’m going to get a job,’ ” he told family and friends.

But it wasn’t so easy. Cloonan went eight months without one. He knew he had to get creative. He read every news story he could about Cuba, and contacted nearly all the sources named in the articles and introduced himself.

He eventually heard from a California-based company, Cuba Cultural Travel, and by August 2015 had been offered a job leading tours on the island. In September, Cloonan went to California for training, and by October he was in Cuba.

He has found a lot to love about Cuba.

“As far as what the country and people are like, they love Americans, first of all,” Cloonan said. “We are known as good tippers. There is a collective resentment about the American occupation of Guantánamo, but that is aimed at our government. Fidel was always careful to separate the anger at our government from Americans as a people.”

Cloonan said Cubans are always willing to help each other and that resolving issues and struggling together are part of daily life. Celebrations begin when day turns to night, he said.

“Nighttime is often a party on the Malecón,” he said, referring to Havana’s boardwalk. “No enforced drinking age, no open-container laws. There is music and dancing everywhere all the time. Just no drugs; they are very serious about that.”

Cubans prize the island’s white-sand beaches and crystal clear waters, which are home to coral gardens and hundreds of species of fish. Cloonan said he favors Havana, the nation’s capital, and its bar and restaurant scene.

“The area surrounding the capitol building is my favorite place to go,” he said. “I enjoy the rooftop bar at the Inglaterra hotel, and the Parque Central hotel staff is unbeatable. The Yellow Submarine bar in Vedado is a cool stop as well. It’s Beatles themed, right next to Parque John Lennon.”

Cloonan can’t stay on the island permanently. He must leave at least every 30 days because of the requirements of the visa granted by Cuba. When his visa expires, he either returns to New York or goes to Miami overnight. He stays at Airbnbs when in Cuba.

“It’s been a wild ride,” he said. “Every trip is different.”

Cloonan has been on tobacco farms, urban farms in Havana, art museums and family-run paladares, or state-approved restaurants people operate out of their living rooms. He has also been to Ernest Hemingway’s former home, where the famed writer lived for 20 years as an expatriate and wrote “The Old Man and the Sea.”


Cloonan has made 17 trips to Cuba and given about 30 tours. As a result, he said he is fluent in Spanish. He said a typical tour group numbers from eight to 20 people, but that he has led tours with up to 65 tourists. Tours last from four to 10 days, he said.

Cloonan’s experience has caught the attention of professors at Stony Brook, who invited him to be part of a panel discussion in December about the impact of Fidel Castro’s death on Cuba.

Cloonan’s involvement with Cuba “was exceptional timing because it came right at the moment the Obama administration was beginning this rapprochement to Cuba,” said Eric Zolov, director of Stony Brook’s Latin American and Caribbean studies program.

“It’s wonderful to have him come back as an alumnus,” he said, adding that Cloonan has “tremendous insider knowledge.”

Rick Ricioppo, a professor at Stony Brook’s journalism school who helped lead the trip that was Cloonan’s first to Cuba, said he uses Cloonan as an example when he tells his students how hard they will have to work to land a job in the media or other fields, no matter where they are.

“He didn’t really fall into it,” Ricioppo said. “He worked at it.”

Stony Brook’s journalism school was so impressed with Cloonan that they asked him to serve as their guide for another student trip to Cuba the school sponsored last year.

Cloonan said that in his work “it’s very crucial for me to stay neutral on political issues. I see my role as to explain things that people don’t understand about the other side, and I do that with the Cubans when I speak with them, too.”

Still, he notes that while Americans generally have a negative view of the Cuban Revolution, “if you were to go to Africa and places like Angola and Namibia and you ask them about Cuba, they hail Cuba as this great country, this tiny little country that stood up for us and helped us achieve independence against our colonizers. That’s not an opinion we would hear in the U.S.”

The United States and Cuba are “like a married couple that got divorced and now are reuniting after 50-plus years,” Cloonan said. “After all that time apart, it takes a little time to get to know each other again. My role is to reintroduce the two societies.”

Cloonan said problems and conditions you see in other parts of the world are not present in Cuba, which took him by surprise.

“It’s what you don’t see that is most impressive,” he said. “Cuba does not have chronic violence; it’s the safest country in the hemisphere. It does not have homelessness, or starving people. We have that in the U.S. It does not have people without access to health care, as we have here. Education is free, pre-K through Ph.D. There is no debt — mortgage, medical, student loans, credit cards, car loans, et cetera. But it’s hard to recognize these things when you first land, because you are struck by the 1950s cars, crumbling infrastructure and lack of American anything.”

Cloonan said his most memorable experiences in Cuba include the Rolling Stones concert. He arrived at Ciudad Deportiva (Sports City) at 10 a.m., even though the concert was not until about 8 p.m. Hundreds of thousands of people attended.

“It was insanity,” Cloonan said. “When they opened the gates, everyone ran up to the front. We were all squished in, body to body. You couldn’t move for hours because it was so tightly packed in there. There were no concessions, no anything. You were just there, waiting for the show to start.”

It wasn’t just a concert but a political statement, he said. Rock and roll had been banned for decades under the Communist regime.

“For them to come down and do that concert, it really signifies that the West is coming back into Cuba now and there is a bit more freedom and things are really opening up,” Cloonan said. “It was really a monumental thing. People were so excited because they never thought something like that would happen.”

A man was “in tears because he never thought he would see somebody like that come to Havana,” Cloonan added.

Obama’s visit the same week was also unforgettable, he said. Havana virtually shut down for the three-day visit. Cloonan was in the stadium when the Tampa Bay and Cuban baseball teams faced off. Americans in the stands good-naturedly chanted “USA! USA!” The Cubans responded with “Cuba! Cuba!”

“It’s been such a wild ride with Obama’s announcement and his visit and the baseball game and the Rolling Stones,” Cloonan said. “I couldn’t have seen any of this coming.”

Glimpses of Cuba

Cuba is a long and narrow island that is the largest in the Caribbean. The island’s official name is the Republic of Cuba, and nearly 11 million people live there. It is also the habitat of the world’s tiniest bird, the bee hummingbird, which in adulthood is just 2 inches long. Cuba’s beaches are characterized by crystal-clear waters and delicate white sand, and its waters are the habitat of some 500 species of fish, 200 sponges, coral gardens and caves.

More about Cuba:


Number of miles Cuba is from the coast of Florida


Number of official currencies. One is the Cuban convertible peso, the other is the Cuban national peso.


Number of mountain ranges


At the end of the Spanish-American War, a defeated Spain signed the rights to its territories — including Cuba, Puerto Rico and Guam — over to the United States.


Date that Fidel Alejandro Castro Ruz, a charismatic, anti-U.S. revolutionary, seized power. Castro died Nov. 25, 2016.

Vintage wheels. Cubans call the old American cars that are ubiquitous in the country “máquina,” which means “machine.”

Sources: Time magazine; National Geographic;;

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