This study examines how ICTs have supported equitable development of online distance learning for students in primary, secondary, and tertiary education systems across the Caribbean. By presenting data obtained through interviews with government officials and other key stakeholders in five countries and territories - Barbados, the British Virgin Islands, Guyana, Jamaica, and Trinidad and Tobago – the study highlights learning continuity challenges and successful adaptations specific to the subregion during the COVID-19 pandemic. The study identifies best practices and recommendations to integrate ICTs in education systems during the pandemic and to ‘build back better’ national education systems towards greater efficacy and inclusivity across student populations.