A : is the aswer This westernmost chain is the largest island group in the region. It contains the four largest islands in the Caribbean. They are Cuba, Jamaica, Hispaniola (the island on which the countries of Haiti and the Dominican Republic are located), and Puerto Rico. Cuba is the largest island in the group covering 40,543 square miles (105,006 sq km). In times past, when sea power determined a country's strength, the islands in this group were strategically important because of their proximity to the United States. They were also stopover points for ships traveling between Europe and the New World.