An eight-day study tour of Cuba became an eye-opening experience that highlighted a country struggling to feed and house its population in the 21st century, while stuck in a confrontational cold war past. Alan and Sharon Kotok describe their experiences as part of a group of University of Iowa alumni who visited Cuba in January 2013. From this tour and their careers in business and foreign affairs, the Kotoks propose 21st century solutions harnessing entrepreneurship, sustainability, and freedom of expression to encourage a thriving and democratic U.S. neighbor.