Let's go to Cuba!
January 22-26, 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. We 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. Our goal is to help you understand the complexities.
We 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. We 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.
Sample Itinerary
While the final itinerary will be confirmed in the weeks before the trip, please view the draft itinerary below to get a sense of the wide array of meetings and sights that you can expect to experience.
What's Included?
The cost per traveler of $3,250 single occupancy, $2,750 double includes:
• 4 nights’ accommodations with breakfast
• All group meals as indicated in the itinerary
• Professional, bilingual guides
• Ground transportation
• Health insurance while in Cuba
• Admission to all museums and public buildings
Travelers are responsible for making their own arrangements to and from Havana. In Cuba, we will partner with Cuba Educational Travel for all other arrangements.
This policy trip complies with all U.S. Treasury Department regulations.
Reserve your spot today
In order to keep the trips intimate and educational, we only offer a limited number of seats for each trip. Travelers can secure their spots with a deposit via check to Art of Diplomacy Tours, LLC and by signing the sales agreement. If you have questions, please reach out to us anytime.