The island states and European/US-controlled territories, situated within (or contiguous with) the Caribbean Sea and the mainland units usually classified with them: Belize, Guyana, Guyane, and Suriname, constitute this region.

For its size, it has exhibited great diversity in geography and micro-climates, colonial and post-colonial history, constitutional arrangements, official and vernacular languages, economic prosperity, political stability, and social differentiation.

Archaeologists identify settlements in the region from before 4000 BCE, with agriculturalists appearing after 500 BCE and Taino chiefdoms from about 1200 CE. The business models, intro­duced by the Europeans after arriving in 1492, sought the rapid extraction of economic values with little regard for the indigenous peoples or their economic practices. Despite this, the latter have left a mark in terms of the use of technologies in indigenous crops, and more broadly in areas such as fishing and small farming.

Mercantilist notions drove the Europeans to prioritize precious metals but little was found. Salt, timber, guano, and non-precious ores were subsequently of greater significance, and planta­tion agriculture provided greater wealth. Colonial trading monopolies, which Spain, Britain, and France sought to impose, were another element of mercantilism. Exclusive rights to engage in particular enterprises were standard, although frequently evaded, with mainly Dutch free ports providing an alternative. The latter received praise from Adam Smith, who criticised the prevailing mercantilism perspectives and provided economic arguments against colonialism.

Exploitation, racism, and use of state power by vested interest pervaded. Indigenous and African slave populations were so brutalized that they failed to reproduce at self-sustaining rates. The racism which justified this brutality later hampered certain groups' entry into lucrative employments and business ventures; race, color, and ethnicity remain important up to the present. The propertied classes imposed tax and other regimes to strengthen their pre-eminence, limit prospects for smaller property owners, and undercut the bargaining position of the laboring classes.

Absentee ownership was significant in some countries, and its negative effect was com­pounded by the metropolitan merchants' control over trade, and mercantilist opposition to certain types of production in the colonies. Varied topographies and patterns of settlement impacted the degree to which agriculture thrived, peasantries developed, markets in local products flourished, businesses catering to local needs prospered, and mercantile-plantation elites exercised hegemony; but even with respect to the latter, there were differences. For example, in Barbados locals maintained control, but in Cuba, Guyana, and Jamaica, US or British trans-national firms came to dominate agricultural production and/or trade in the twentieth century. Trans­nationals controlled the mining and refining of minerals such as bauxite, nickel, and petroleum, and entrenched themselves in the financial sector, and later, tourism. Manufacturing, outside of agricultural processing, developed slowly based on local markets, but by the 1940s states were promoting its growth. US businesses used Puerto Rico as a base for exports to their home market, but elsewhere new industries were mainly protected, finishing operations for local markets. Soon after the 1959 revolution, state enterprises became the norm in Cuba and grew significantly in some countries from the 1970s. Caribbean economies are open and, in many cases, the main production units have been plantations and/or branches of vertically integrated trans-national firms. National business cultures dominated by margin gathering, based on import-export trade, are common. Where this is the case, production-oriented innovation is not highly developed. By privileging an academic orientation and professions such as law and medicine, education systems have often re-enforced this tendency.

Traditional export agriculture has declined in most countries, while food imports have grown. Uncompetitive manufacturers have shut down and services have become more important. The oil and gas sector has prospered, although refining and transhipment of oil has declined in some non-oil-producing countries. Other minerals have had mixed fortunes with precious stones and gold being most buoyant. Trans-nationals often continue to dominate in the minerals, tourism, and financial (including offshore) services sectors. Some have taken over long established activities such as the production of alcoholic beverages. Where it still exists, large scale agriculture varies as to the prevalence of state, local, or foreign ownership. National enterprises have done better in merchandising and in small scale production and services for the local market. Some local firms have developed to be major players in national or regional manufacturing, and more so hospitality, tourism, and finance, where some have extended beyond the region. Services are provided to the Caribbean diaspora in North Atlantic countries; notably, for the transfer of remittances on which many countries depend.

Although under reform, the state sector remains paramount in Cuba. It also retains a strong presence in some other countries or in particular sectors, such as transport. The pervasive informal sector is an area where women have long had an entrepreneurial presence, notably in trading. Failure to comply with regulatory frameworks and/or corruption are common in some countries but not uniformly so. The level of national policy consensus varies widely, and conflict in some countries is exacerbated by racially or ethnically based divisiveness. Criminal businesses have prospered in the drug trade and in extortion, cyber-crime, and other scams in some countries, especially where links between criminal business, legal business, and the political and state systems are evident.

One indicator of the region's diversity is the date when national/central banks were established: ranging, for example, from the 1820s for the Dutch Islands to the 1980s for Belize and the English-speaking Eastern Caribbean. Geopolitical shifts have diminished bilateral North Atlantic institutional interest in the independent countries (post-2010 earthquake Haiti is an exception), but dependent territories are better able to secure transfers. National debts are generally large and there have been recent defaults. The region is not well integrated, especially across language communities, but various efforts have been made at political, economic, and functional cooperation. A shift towards strong internal ties, long advocated by regionalists, has not emerged, but there have been recent changes in external relations. Here, China is most significant, but Venezuela (especially under Hugo Chavez) and Brazil have also been important.

Regional diversity can be seen in founding dates for national universities which are even more varied than those noted above for Central Banks. Compare, for example, Dominican Republic, 1538 (closed during most of the nineteenth century); Cuba, 1728; Puerto Rico, 1903 with Haiti, 1942; English-speaking Caribbean (Jamaica campus), 1948; Suriname, 1966; and French Caribbean, 1982. Yet this indicates nothing of the diversity in the nature of the universities or the existence of earlier tertiary institutions. There was some teaching of political economy in the nineteenth century, but economics was generally first introduced from the 1940s or 1950s or later, and is still only taught as part of the business curriculum in some cases. With or without institutions, there was awareness of the development of political economic ideas. For example, Smith's Wealth of Nations was read in Jamaica within a year of its publication, and in Cuba the Sociedad Economica de Amigos del Pais maintained between 1818 and 1824 the first political economy chair utilizing, as a text, the work of Jean Baptiste Say.