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Governments around the world, including those within the Caribbean region, have committed to investing in the provision of “Education for All” as a critical sustainable developmental strategy (Moretti & Frandell, 2013). While there have been commendable strides in the achievement of this goal, the attitude of students towards school and learning continues to be an important variable in overall educational outcomes. This therefore necessitates further studies into students’ attitudes and its overall influence on educational outcomes. The formation of attitudes is often experiential (Mensah, Okyere & Kuranchie, 2013) as based on the experiences within the classroom, students develop positive or negative attitudes towards school and learning. This attitude consequently affects the quality of students’ academic performance (Kpolovie, Joe, & Okoto, 2014). This study, informed by Krathwohl’s et al. (1964) Taxonomy of the Affective Domain which focuses on the attitudes, values, interest and appreciation of learners, examined the attitude towards school and learning among 1477 secondary school students across four (4) countries in the Eastern Caribbean. The study guided by a survey design utilized Gray’s (1983) 24-item attitude towards school scale and was centred around a central question: “What are the Caribbean students’ general attitude towards school and learning?” More specifically, the study explored whether differences exist in students’ attitudes by gender and socio-economic status, as well as the main aspects of schooling towards which students expressed the most negative, and most positive attitudes. The preliminary data analysis indicates an overall moderately positive attitude towards school and learning; the mean attitude to school score was 15.21 (SD=4.794). The results further showed that there was no statistically significant difference in students’ attitudes towards either school or learning by gender; the mean scores on attitude towards school between the two groups (t= 1.773, df=1455, p= 0.076) indicating that the relationship between gender and attitude to school and learning is negligible (r=-0.051) based on Burn’s (2000) classification. In addition, there were aspects of schooling towards which students had more positive attitudes such as: students saw the benefits of schooling to assist them in getting a job, learning new things and helping them to think better. Conversely, these students generally agreed that they wished they did not have to go to school at all, they would rather stay at home, or go to the dentist and doctor rather than go to school. While there was not a statistically significant difference between the general attitudes of boys and girls, there were some notable differences in attitudes in relation to some specific aspects of schooling and learning. These findings are quite consistent with other international studies with similar goals (OECD, 2013; Gorard & Huat See, 2011). The results of this study have implications for the strengthening of inclusive education policies and practices in Caribbean schools, and for further achieving regional Sustainable Development Goal (SDG) 4.