Trinidad and Tobago contains the majority of the Caribbean's oil production. In 2007, the country produced 163,320 barrels per day (bbl/d) of total oil production, of which 121,150 bbl/d was crude oil, the remainder mostly consisting of natural gas liquids (NGLs). In 2007, Trinidad and Tobago consumed an estimated 29,000 bbl/d of oil, allowing it to export a sizable amount of its production. In recent years, the country’s oil production has begun to rebound; despite the fall in 2007, oil production is still above the level seen in 1998.

Most oil production in Trinidad and Tobago occurs offshore, concentrated off the southeastern and southwestern coasts. In January 2005, production began at the Greater Angostura field in Block 2(c), the first oil production to occur off the northeast coast of Trinidad. Operated by a consortium led by BHP Billiton, the Angostura field contains an estimated 310 million barrels of recoverable reserves. Overall, the largest crude oil producers in Trinidad and Tobago include Petrotrin and BHP Billiton. Important producers of NGLs in Trinidad and Tobago include the Phoenix Park gas processing plant and the Atlantic LNG project.

Cuba produced 52,000 bbl/d of oil in 2007, roughly the same as 2006. In 2007, the country consumed an estimated 205,000 bbl/d, making the island a net oil importer. Cuba's oil production has increased significantly in the past two decades, with the country only producing 16,000 bbl/d in 1984. Most of Cuba's oil production occurs in the northern Matanzas province, producing a heavy, sour crude that requires special processing. Currently, two Canadian companies, Sherritt International and Pebercan, are producing oil in Cuba, under joint-venture production agreements with state-owned oil company Cubapetroleo (Cupet). Much of this production occurs onshore, though there is some offshore production in very shallow coastal waters. Cuba’s oil production seems to have largely stabilized in the near term, with any additional increases in production dependent upon the discovery of substantial new reserves (see below).

There has been considerable excitement over exploration activities in Cuba's offshore basins, especially its portion of the Gulf of Mexico. Industry analysts have reported that there could be at least 1.6 billion barrels of crude oil reserves in these basins. However, exploration activities have, so far, been somewhat disappointing. In July 2004, Repsol-YPF announced that its exploratory well in the Gulf of Mexico had discovered high-quality crude oil, however the company noted that it had not discovered commercially-viable quantities. In 2007, Cupet and Venezuela’s PdVSA concluded an agreement to jointly explore Cuba’s offshore areas, and the country has signed other exploration agreements with Malaysia’s Petronas, India’s OVL, and Vietnam’s Petrovietnam. Industry reports indicate that larger exploratory drilling efforts could begin in Cuba’s offshore basins in 2009. There have been concerns raised in the United States regarding the close proximity of any potential Cuban oil production to Florida. However, as oil companies have not yet conducted a comprehensive survey of the area, it is difficult to predict the exact locations of any potential production platforms.

While Barbados does not have significant crude oil reserves, it does maintain a small amount of domestic production. Oil production in Barbados during 2007 averaged 1,000 bbl/d, while the country consumed an estimated 8,000 bbl/d. As Barbados has no refining capacity, its oil is refined elsewhere and then returned for domestic consumption.

Many of the Caribbean countries import oil from Mexico and Venezuela under favorable terms. Under the San Jose Pact, Barbados, the Dominican Republic, Haiti, and Jamaica received oil and refined products from those two countries. Cuba also receives crude oil and petroleum products from Venezuela at a discounted rate. In 2005, nearly all Caribbean countries signed the Venezuela-backed Petrocaribe initiative. Under the program, Venezuela sells crude oil and refined products to these countries under favorable financing terms.