In March of 2016, the Obama family went on a whirlwind 3-day tour of Havana, Cuba—the first visit to the island by a sitting U.S. president since 1928. The occasion was the reestablishment of diplomatic relations between the two countries and for Obama, the trip was a careful balance of politics and pleasure. In this episode, we discuss the ins and outs of how the trip came to be after a century's worth of contentious history between the two countries, and how things have fared since.