In June 2001, I had the chance to fly to Cuba for a story about Gulfstream International Airlines, the Miami-based carrier that was doing charter flights to the island nation at the time. Scheduling conflicts kept me from making that trip, and I always regretted it.

Fast-forward to March 2016, when former President Barack Obama relaxed travel restrictions on trips to Cuba. It made it easier for U.S. citizens to visit. Thanks to low mileage requirements on Southwest Airlines, I was able to get two tickets to Havana and our family of three visited for four days in June.

Being in Havana on the day President Donald Trump announced he’d be reinstating some old restrictions on travel to Cuba made the trip especially interesting.

While WiFi access was limited, I was able to download a story on the proposed changes to my iPhone. Everyone we met wanted details since the policy will impact Cubans as well. I even shared the details with a Cuban news crew. (Newsgathering in Cuba, like most things, is controlled by the government, which means that citizens don’t always get news quickly.)

Source: Boston Consulting Group
Source: Boston Consulting Group

How does this affect my travel to Cuba?

The Departments of Commerce, State and Treasury will issue regulatory amendments “in the coming months” to the existing rules in order to implement the policy outlined by President Trump on June 16.

What does this mean for travelers?

One of the most popular of the categories allowing U.S. citizens to visit Cuba was “people to people.” Under the new policy, that category would be eliminated, meaning that individuals won’t be able to go to Cuba unless they are participating in a group educational exchange activity approved by the Department of the Treasury. It must be designed to enhance contact with the Cuban people and promote their independence from Cuban authorities.

Travel via airlines and cruise ships will still be allowed. Visitors will be discouraged from making travel-related transactions with the government, instead encouraged to spend with Cuba’s private businesses.

Trump’s announced changes don’t take effect until new regulations are issued, so if you made your Cuban travel arrangements before June 16, the old rules still apply.

(Courtesy of Benét J. Wilson)
(Courtesy of Benét J. Wilson)

U.S. travel to Cuba before Obama

Before the brief relaxation era began in 2016 under Obama, Americans could only book trips to Cuba in groups or if they were traveling for work or a cultural exchange.

Jackie Jones, the assistant dean for programs and chair of the multimedia journalism department at Morgan State University, took her first trip to Cuba in June 2014 through the Institute of Advanced Journalism Studies (IAJS), a nonprofit organization that provides reporting and professional development opportunities for black journalism students and mid-career professionals.

Morgan State students go to Cuba twice a year and are currently working on a documentary with students at the University of Havana. Since IAJS has been taking students to Cuba since 2001, the organization has developed a friendly relationship with locals.

“They were always very kind and receptive,” Jones said. “They don’t see Americans as the problem. It’s more between the countries’ governments. They respected President Obama and hoped he would find a way to open the governments more.”

Delia Harrington, a Boston-based freelance travel writer, first went to Cuba in 2010 as a student spending a semester abroad. She has been back for work twice since. Each time, Cubans have been receptive.

“As an undergraduate, I was a political science minor and whenever people heard that they wanted to talk politics,” Harrington said. “Cuban people spoke freely, talking about their leaders and their lives. They were incredibly informed about our political system.”

When it comes to Trump’s proposed changes, both women saw them as hurtful to those they purport to help.

Will the changes affect the tourism industry?

On her trips, Jones saw Cubans earning extra income from tourism, which improved their quality of life. She met a female doctor who, along with her economist husband, bought an apartment in Havana.

“They rent out the apartment and the husband does a car service for guests,” Jones explained. “He makes far more money doing that as compared to his economics job. Raúl Castro opened the door to private ownership that Fidel never would have.”

Emily Morris, an associate fellow at the University College London’s Institute of the Americas, wrote in an analysis that “reinstating restrictions on U.S. travel would most acutely affect those who have enjoyed the greatest benefit — including the private restaurateurs, bed and breakfast owners, and taxi drivers of Havana — rather than the Cuban state.”

“There is palpable concern in the Cuban government and amongst Havana’s entrepreneurs about the risks posed by the new U.S. administration, particularly given the pro-sanctions posture of some senior appointees.”

Prior to Trump’s announcement, the Boston Consulting Group estimated that by 2025, as many as 2 million U.S. travelers could visit Cuba each year. However, some airlines didn’t experience high demand and canceled routes close to when Trump tweaked the U.S. policy.

Frontier and Silver Airways stopped flying to Cuba altogether in early June, and Southwest announced that it would end two routes to Varadero and Santa Clara on Sept. 4. (The airline will keep its route to Havana.) American Airlines, JetBlue Airways and Delta Airlines still fly to Cuba.


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