The article proceeds as follows. First, it combines a sketch of older Caribbean-African relations with more recent cooperation-related undertakings, framing mooted CARICOM-AU summitry and its precursor diplomatic milieu by analytically situating both regions in international affairs-related high politics. I show that some recent foreign policy stances of a handful of CARICOM Member States provided early, if incomplete, signals as regards the regional push for a deepening of CARICOM-AU relations. Second, this article delves into the fundamental issue of how to cast Caribbean-African relations while also taking a closer look at summit diplomacy and the main drivers behind African and Caribbean countries' foreign policies. Third, and from a CARICOM vantage point, it pinpoints the role of geopolitical and geo-economic dynamics in the making of summitry with the AU. In the case of the geopolitical dimension, the article highlights recent systemic shifts in relations between the Organisation of African, Caribbean and Pacific States (OACPS) and the European Union (EU). The article also examines geo-economic shifts germane to the Africa axis of CARICOM Member States’ foreign policies, underlining the associated value that CARICOM attaches to the summitry enterprise. The article concludes with a look back at core lines of argumentation, along with a look ahead at the practical implications of the COVID-19 crisis and other conditions vis-à-vis the prospects for deepened CARICOM-AU relations.