It’s an island in the middle of the Caribbean Sea a little bit bigger than Tennessee, but ever since Fidel Castro and his band of Communist rebels took control of Cuba in the late 1950s, Cuba has had an outsized presence in the American consciousness.

Thanks to strained U.S.-Cuba relations and a trade embargo that began with the Kennedy administration, the island became a land that time forgot and was essentially off-limits to Americans for decades. However, beginning in the late 1990s, the rules around visiting Cuba began to relax and by 2016 U.S. airlines and cruise ship companies were permitted to bring Americans directly to Cuba.

The allure of being able to visit a place that was once off-limits was very appealing. By 2017, more than 600,000 Americans visited the island. However, with a new administration in the White House, there was a dramatic about-face on the rules governing American travel to Cuba, culminating with a decision in June of 2019 to revoke the “People to People” travel category under which the vast majority of Americans visited Cuba.

This new policy will essentially end the “veiled tourism” to the island. Cruise ships are no longer allowed to bring Americans to Cuba, and the tourists who came to tour cigar factories and Hemingway’s home will have to look for someplace else to go.

After more than 50 years of dramatic history, United States-Cuba relations are once again front-page news. But if you read between the lines, you’ll see this is still a promising time for the people of Cuba and the Americans who want to make a difference in their lives. While the “People to People” travel category has been eliminated, there is a separate but similar approved travel category called “Support for the Cuban People.” The intent of this category is to support independent activities and entrepreneurship that strengthen civil society in Cuba and promote economic independence among the Cuban people.

We have been bringing Americans to Cuba since 1997, and while many come to experience the faded Colonial splendor of Havana, it’s really always been the interactions with the people of Cuba that make the greatest impact on Road Scholar participants. Road Scholar’s relationships in Cuba, developed over 20 years, are deep, sincere and characterized by integrity and respect. In every town Road Scholar participants visit, the local people know Road Scholar and want to share their experience and point of view — a view that goes far deeper than the day’s headlines.

Road Scholar’s experiences in Cuba fully comply with the requirements of the “Support for the Cuban People” travel category. Our goal is to empower the people of Cuba. Meeting with local artists, musicians, organic farmers and others who own their own businesses, you’ll see there is a true dialogue that takes place. One of the most popular activities for Road Scholar groups is viewing performances and meeting with dancers from the dance company Malpaso. Fernando Saez, Malpaso’s founder, says, “Life is the art of making friends, and for a dance company to have followers and loyal friends like the Road Scholars who meet with us is essential to our success.”

A spirit of entrepreneurship among the Cuban people and a renewed sense of independence has taken root over recent years, and Road Scholar groups are a large reason why. Learning about authentic Cuba from Cuban people is what gives so much impact to the Road Scholar experience — for both Americans and Cubans alike.

See Road Scholar’s complete collection of programs in Cuba →

About the Author
JoAnn Bell, Senior Vice President of Program Development, develops and manages more than 5,500 learning adventures in 150 countries and 50 states. JoAnn's extensive travel industry experience informs her expert insight on everything from where to find the world's most charming streets to must-see hidden gems across the globe.


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