Impressions from various discussions on regional integration initiatives in Africa demonstrate that the idea of “free movement” between states is not new and, therefore, makes migration inevitable. Although migration has been characterised as essential in the search for ‘African solutions to African problems’, with the highest number of a young generation in the world, the African continent is severely compounded by factors that impact on emigration. These include political instability, structural violence and economic bottlenecks. This paper focuses on the African youth (14 -30 age according to EAC policy), more specifically, on the youth in the East African region. Building our arguments on human capital theories, the paper aims to explore youth migration both within the region and abroad over time. We look at how young people’s imaginations about the future shape their views about life in the EAC region vs. life in Europe and beyond. Looking at the challenges and opportunities of youth migration, and using a random informal discussion with university young people from EAC countries, coupled with secondary data on regional integration and migration, the study seeks to contribute to the on-going conversations and policy recommendations for a sustainable regional free movement and integration with the involvement of the youth.