Simon Reeve starts his Caribbean journey in the Dominican Republic, Haiti and Puerto Rico.

Simon enters continental Central America in Nicaragua, the poorest Americna country after Haiti, and finds that's largely the fault of the Sandinista government's misrule after the Contra civil war. Locals grimly disagree about the projected larger alternative to the Panama Canal, costing thrice the GNP, massive expropriation -disrupting natives- and wildlife destruction without guaranteed jobs for poorly schooled locals. in Honduras, a violent political history seems overtaken by drug-related gang wars, terrorizing the civilians and forcibly recruiting even pre-teens. Simon ends his journey on Jamaica, where re-migrants from the US play a major part in the ambitious government's efforts to turn the tide by cleaning up its own ranks, especially the corrupt police, and modernize the economy.

On Barbados, Simon examines the contrast between the very rich's opulent beach houses and the relative poor local dwellings. On nearby, poorer, yet soil-rich St.Vincent, he visits the local farmers' cannabis plantation on the volcanic slopes and their prime minister, considering legalization of the 'soft' drug. In Venezuela, he finds a rich oil-country under terrible government can fall deeper into misery, over the Colombian border, a major smuggle route, that a former guerrilla battleground can rehabilitate.