Higher education is considered as one of the most essential factors in influencing societal changes, due to its ability to help formulate good decision making in every sphere of modern society, in businesses, education, politics and science. Higher education over the years has significantly increased, thus given rise to many opportunities for those who pursue it. The Caribbean students, like the rest of the world seek to benefit from higher education, not only for enhanced academic knowledge, but also for socio-economic development. Due to its sluggish development, brittle economy and lack of natural resources the Caribbean region faces many economic challenges in making quality higher education accessible to all of its occupants. The purpose of this study is to investigate and compare the challenges of low output of higher education and availability of higher education institutions in the 21st century in the Eastern Caribbean. The study analyzed database of 37 tertiary institutions in the OECS, while using comparative approach to analyze availability and cost for higher education. Results show that factors that are affecting higher education in the region are accessibility, location, quality of education, institutional costs and unemployment of graduates. We found that increased access in higher education has risen tremendously due to accessibility of technology and factors like globalization, integration-networking and traveling cost. This paper suggests that collaborative approach be taken by governments of the region to increase access and funding for higher education through scholarships and grants.