Long-time friends, Americans and Canadians share many world-views and values. Yet, important differences exist. This study examines one foreign policy where these differences are striking. The United States and Canada have had very different policies toward Cuba, especially since Fidel Castro assumed power in 1959. Canada's policy of constructive engagement stands in marked contrast to the isolationist solution adopted by the American government. Much of the current literature offers traditional economic or domestic interest group explanations for the two policies. This study challenges these conventional narratives. By examining each country's policy toward Cuba in tandem this study demonstrates that there is far more than domestic political or economic calculations involved in the formulation of these foreign policies. Adopting a constructivist approach, this study will show that differences exist over Cuba because the two countries are different in other ways—they have their own identities, values and perceptions that contribute to the formation of very distinct approaches toward this island regime. Canadians and Americans perceive Cuba through different lenses. The American identity as an exceptional country and their corresponding view of Cuba as inferior as well as the perception that Cuba is within the American sphere of influence has affected the relationship between the United States and Cuba since the days of the Monroe Doctrine. The American identity as the guardian of freedom and democracy helped to construct American policy. After 1959, Cuba was seen to be an anathema to everything the United States represented. In contrast, the Canadian identity as “not American” and the need to assert this in foreign policy, as well as their identity as a good international citizen with its emphasis on values such as dialogue and compromise have greatly influenced the Canadian perception of Cuba. In sum, the examination of identity and its related values, perceptions, and norms offers an alternative way of making sense of US-Cuban and Canadian-Cuban relations. These two case studies reveal how these variables influence foreign policy and enable us to better understand Canadian and American foreign policy as well as international relations.