Regional development planning is proponed as an important tool for development implementation in small countries, both at the level of each nation and at the level of the interactions between small nations within the Caribbean. The assertion is substantiated on the basis of the need to take into consideration the historical sociological and physical determinants of developments in the preparation and implementation of economic development projects. The paper argues for regional planning to boarden out from the original physical emphasis posited on a natural resource priority (an outlook functional to the needs of nations with “empty perifheries”), to fill the conceptual and technical spaces of regional socio-economic programming and regional administration. The argument is developed further through the analysis of five experiences of regional development that used the approach outlined involving countries like Jamaica, Surinam, Saint Lucia and a multinational project of renewable energy.