The growing reconciliation between the United States and Cuba has created a unique opportunity for U.S. business and hospitality students to observe and experience first-hand an economy in marked transition. Attempting to balance the tenets of socialism with a rapidly growing reliance on capitalism creates a rare learning environment for students. This article presents the plan for a 10-day faculty-led study abroad program to Cuba. The program is divided between the two (arguably) most important destinations in Cuba: the economic and cultural center, Havana, and the tourism powerhouse of Varadero. At each destination, students are engaged in lectures, site visits, research, and cultural experiences.