The countries in the Caribbean Community (CARICOM) share a history of colonialism that has left an indelible mark on all their institutions and systems of socialization, including education. A dominating theme across these countries is the question of equitable access to quality education at all levels, an issue that increasingly finds resonance in the 21st century’s technological era. The region has generally made important strides in the areas of universal access to basic education and increasingly to secondary education. Tertiary education has also been prioritized under the new “knowledge economy,” with many countries exceeding the 15% of qualified cohort (those who are academically qualified to be enrolled) that was set as a regional target in 1997 by Caribbean governments. Yet, even with these strides, the education project is still incomplete, with new and continued challenges of affordability and quality. These concerns are now incorporated into the Caribbean’s deliberate attempts at regionalism through the Caribbean Single Market and Economy (CSME), which serves as CARICOM’s organizing mechanism to face the new opportunities and challenges of the 21st century’s knowledge economy. These regional and development plans are expressed in CARICOM’s Human Resource Development 2030 Strategy (HRD Strategy), a multiyear development plan that is predicated on educational advancement across the region. The Caribbean’s educational achievements, equity challenges, and development plans are best understood in a historical context that captures the social, political-economic, and cultural idiosyncrasies of the region.