Art of Diplomacy Tours: The Cuba Experience (Registration Open Through Nov 15)
January 22, 2026 – January 26, 2026
Curious about Cuba? Ambassador (ret.) Charles Shapiro and Amanda Mattingly are leading a trip to Havana January 22-26, 2026 to meet with a wide range of Cuban academics, artists, small business owners and others to figure out what is going on and how the United States should respond.
The group will meet with the Acting U.S. Ambassador to Cuba as well as the Cuban Ministry of Foreign Affairs (requested). The Cuban economy has been crushed by U.S. sanctions, poor Cuban governance, and Covid in 2020. In 2021 and 2024, protests broke out and were repressed by the Cuban government. One thing is sure: the sound bites from the U.S. right and left miss the complexity of Cuba. The goal is to help you understand the complexities.
You will fly commercial airlines via Miami and meet in the Havana airport the late morning of Thursday, January 22 and depart on flights Monday, January 26. The group will stay in privately owned, comfortable boutique hotels and travel around town in classic American cars. All trips are legal under U.S. law and licensed through the U.S. Department of Treasury’s Office of Foreign Asset Control.
