This study investigates the barriers to and facilitators of the inclusion of learners with special education needs (LSEN) in the schools of three member countries of the Organisation of Eastern Caribbean States (OECS). Students who require special education provision continue to face challenges in accessing quality equitable education in schools in the OECS. As a result, members of this marginalised group could face negative educational and employment outcomes (Armstrong et al. 2005; Miller 2000; Peters 2003). Inclusion has been embraced by educators as a means of creating equitable, informed and democratic societies. The successful practice of inclusion that meet the needs of diverse learners could see LSEN and communities reap the full benefits of a quality education system (Acedo 2008; Ainscow, Farrell and Tweddle 2000; Kelly 2012; Peters 2003; UNESCO 2005). The study is significant because it specifically explores the practice and strategies of inclusion within the education systems of the often overlooked small island developing states of the Eastern Caribbean, thereby contributing to the literature available on the sub-region. Underpinned by a qualitative approach to research design, and using a constructivist grounded theory (CGT) to collect and analyse data, the research engaged five groups of participants with in-depth interviews: special education teachers, special education students, parents of special education students, Ministries of Education policy actors and staff members of disabled people organisations. The CGT qualitative approach lends itself to reporting the lived experiences of the members of the five participant groups and provides insight into the barriers that have negatively impacted the access to quality equitable education for LSEN. Inclusion has been a global education goal as early as the Salamanca Statement in June 1994 and the Education for All mandate (Ainscow and Sandhill 2010; Miles et al. 2014; Peters 2003; UNESCO 2005). In the OECS, broad strategies intended to facilitate inclusion into education systems include the implementation of universal secondary education and the placement of special education teachers in some schools (Browne 2007; Hinds 2007). However, the findings of this research indicate that deficient policies and supportive structures, a lack of availability of suitable adaptations for LSEN, a failure of parents to advocate on behalf of their child, among other hindrances, continue to frustrate the successful inclusion of LSEN and the successful practice of inclusion in schools. These research findings highlighted eight major themes in which both positive and negative outcomes manifest: legislation and policy; teacher training and professional development; adaptations; resources and support; attitudes and perceptions; education and advocacy; parental involvement; and collaboration and networking. In addition, the evidence adduced indicates that a level of purpose must guide OECS education stakeholders in order to strengthen supportive structures and engage in the transformation of barriers to inclusion into facilitators of inclusion. The study is important because it explores the current provision of special and inclusive education in the OECS from the perspective of not only those charged with the development and implementation of policy, but also from those most affected by the policy. Indeed, a particular research focus is on the challenges participants face and the solutions they suggest. It is hoped that the conclusions drawn from this research can be used to inform the future development and implementation of effective policies and strategies for inclusion in the OECS.