The historical development of astronomy in the Caribbean is reviewed within its cultural and environmental framework. The present status of astronomy in education, research and at the popular level is presented also with the focus being on its development in the island of Trinidad and Tobago in particular. We review what works in small developing islands versus larger developed or developing countries and the peculiar trials and tribulations of our circumstances as well as the rewards of such efforts. The critical role of students and volunteer effort will be highlighted. The psychological and cultural aspect and its role in the development of astronomy in the Caribbean is also explored. The outlook for the next decade will be highlighted with a brief proposal of having a node for TWAN (Third World Astronomy Network) in Trinidad in the Caribbean.