Case Study: Theodore Roosevelt Association


Sometime in the spring of 2011, when regulations on travel to Cuba had once again been loosened to include people-to-people travel, and insightCuba was one of the first organizations to receive the license, the telephone rang in the office of the President of insightCuba. On the other line was Michelle from the Theodore Roosevelt Association (TRA); “Would insightCuba be able to do a program in Cuba that focuses on the Spanish American War”? “Absolutely, said Mr. Popper, we will organize the best Spanish American war program to Cuba”. 

Setting out to fulfill that promise, insightCuba worked hand-in-hand with Theodore Roosevelt Association while planning an itinerary that trails the footsteps of the former President Theodore Roosevelt and the rough riders in Cuba.  Revisiting the places that the late former president had visited in Cuba and seeing history come alive before their eyes, was for this group of travel companions who share a common interest in the legacy of Theodore Roosevelt an experience that few had imagined would come true.  For many, it was surreal to stand on the San Juan Hill and to see the environs where the major battle took place.

As they set about retracing history, they not only furthered their knowledge on the Spanish American war, but they also delved into the cultural richness that Cuba has to offer. Many expressed that is was a treat to interact with Cuban people. In Santiago, the group of 94 travelers was welcomed by an entire neighborhood to a block party. It was a magnificent night with music, dance, food, conversations and plenty of laughter.

“This trip was about making new friends, both on the tour and with Cuban people”, shared one of the TRA members, I had a wonderful time and hope to visit Cuba again someday.”

“We are very pleased to have been part of this great adventure”, said Ronald; the diversity of experiences was great.”