Founded by Ambassador Charles Shapiro and Amanda Mattingly, Art of Diplomacy Tours started with the idea of taking curious, policy-minded American citizens to Cuba. Charles and Amanda led their first delegation trip to Cuba in June 2023, followed by trips in 2024 and most recently in January 2025.

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Charles and Amanda have traveled to Cuba several times over the last 20 years and believe that U.S. government-licensed, people-to-people exchanges such as these make a difference and can open important dialogue between the people our two countries. So much about the U.S.-Cuba relationship is misunderstood, but educational travel trips like these can help Americans and Cubans gain a better understanding of one another. It is our hope that citizen diplomacy and advocacy can help improve U.S.-Cuba relations over the long term. 

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All trips are legal under U.S. law and licensed through the U.S. Department of Treasury's Office of Foreign Asset Control.