Trinidad and Tobago contains the majority of the Caribbean's oil production. In 2008, the country produced 165,420 barrels per day (bbl/d) of total oil production, of which 114,280 bbl/d was crude oil, the remainder mostly consisting of natural gas liquids (NGLs). In 2008, Trinidad and Tobago consumed an estimated 41,000 bbl/d of oil, allowing it to export a sizable amount of its production. The largest oil producer in the country is the state-owned Petroleum Company of Trinidad and Tobago (Petrotrin). Other large producers include BP Trinidad and Tobago and BHP Billiton.

Cuba produced 52,600 bbl/d of oil in 2008, roughly the same as 2007. In 2008, the country consumed an estimated 176,000 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 13,000 bbl/d in 1988. Most of Cuba's oil production occurs in the northern Matanzas province, producing a heavy, sour crude that requires specific processing. Much of this production occurs onshore, though there is some offshore production in 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). In 2009, state-owned Cupet cancelled its production sharing agreements with Canadian firms Sherrit and Pebercan for the Block 7 area, which represents about two-fifths of the country’s total oil production.

There has been considerable interest in exploration activities in Cuba's offshore basins, especially in the Gulf of Mexico. The U.S. Geological Survey (USGS) mean estimate for undiscovered oil reserves in the North Cuba Basin (the basin north and west of the island in the Gulf of Mexico) is 4.6 billion barrels. Cupet estimates that all of Cuba’s offshore basins could contain in excess of 20 billion barrels of undiscovered oil reserves. However, actual exploratory drilling in the area has been, to date, quite limited. In July 2004, Repsol-YPF announced that its exploratory well in Block N27 in the Gulf of Mexico had discovered high-quality crude oil, but not in commercially-viable quantities.

In 2007, Cupet and Venezuela’s PdVSA concluded an agreement to jointly explore Cuba’s offshore areas. A consortium of Repsol-YPF (40 percent and operator), Norsk Hydro (30 percent) and ONGC-Videsh (30 percent) announced that it would drill an offshore exploratory well in 2010-2011. The consortium has exploratory licenses in seven blocks in the Gulf of Mexico. According to media reports, Cuba also signed offshore exploration agreements with Russia’s Zarubzhnieft in 2009. Petorbras announced in July 2009 that it had completed seismic work at its offshore block (Block 37) in the country. As of late 2009, no Chinese oil companies were drilling in Cuba’s offshore basins, according to media reports.

While Barbados does not have significant crude oil reserves, it does maintain a small amount of domestic production. Oil production in Barbados during 2008 averaged 1,100 bbl/d, while the country consumed an estimated 9,000 bbl/d. As Barbados has no refining capacity, its oil is mostly sent to Trinidad and Tobago for processing, with the refined products returned for domestic consumption.