Clay Jenkinson, doing a historical presentation as Theodore Roosevelt in Santiago, Cuba. 2024
A not-so-rough rider, Clay gave a historical presentation as Teddy Roosevelt during a recent visit to Santiago, Cuba.
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Returning from leading a cultural tour of Cuba, the second in four years, Clay offers a new approach to U.S./Cuban relations.
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Clay Jenkinson is currently leading a cultural tour of Cuba, where the group spent time walking the scenic streets of its historic capital, Havana. (Shutterstock)

Catching the Tune in Havana

Now on a cultural tour of Cuba, outside a street-side cafe in Havana, Clay and his guests stumble into a magical, transcendent moment.
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Fidel Castro's cradle is on prominent display at his birthplace in Biran, Cuba. His father's sugar plantation, where Castro grew up, is now a museum.
Fidel Castro’s birthplace, now a museum, is one of the initial stops for Clay and his companions as he leads a cultural tour of Cuba.
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Before setting off for Cuba this week on a cultural tour of the island nation, Clay and his guests stopped in at the Bay of Pigs Museum in Little Havana, Miami.
Thomas Jefferson long harbored a desire to make Cuba part of the newly forming United States. In 1809, he wrote to James Madison outlining his dream to erect a column on the Southernmost limit of Cuba inscribed:
The United States has a long, tortured relationship with Cuba, including Thomas Jefferson’s imperial designs on the island. As Clay travels to Cuba this week to lead a cultural tour, he reflects on a bit of forgotten history between the U.S. and the island nation 90 miles from Key West, Florida.