Caribbean and African ties run deep. They are based on a shared history, culture, and sense of a common identity forged by the slave trade which forcibly relocated more than 10 million Africans to the New World, in the process, creating large centres of African Diaspora in the Caribbean and elsewhere. The common historical experiences of slavery and colonialism inspired formation of the Pan-African Movement in the first half of the 1900’s led by the African Diaspora outside of Africa. Organized around an agenda of de-colonialization and racial equality, spanning several decades, this early period marked the most rich, vibrant and dynamic period in African-Caribbean relations with both groups united around a common agenda. Today, while Africa and the Caribbean engage through multiple points of contact and in different fora, the relationship seems to have lost its lustre and drive. This paper argues that the future of Caribbean-African relations is one ripe with potential and promise, but it requires concerted investments of time, attention and political will to systematically transform the relationship into a political, social and economic force, fit for purpose and suitable for these modern times.