Simon begins his journey around the Caribbean on the island of Hispaniola and its two very different countries - the Dominican Republic, a tourist hotspot, and Haiti, the poorest country in the western hemisphere. He ends this first leg on Puerto Rico, a Caribbean island that is practically America's 51st state. From flying boats to drug busts, Simon explores both the light and dark sides of the Dominican Republic, the Caribbean's most popular tourist destination. He joins the police anti-narcotics division on the front line in the war against international drug cartels in Santo Domingo before crossing the border to Haiti, where he visits the notorious tented camps of Cite Soleil. These slums remain home to many of the survivors of the worst earthquake to hit the island in two centuries. From voodoo ceremonies to dolphin watching, Simon also discovers a vibrant, colourful and thriving side to life in Haiti born out of the country's unique history. Finally, Simon reaches Puerto Rico, an island with close ties to the USA. He visits the tiny, paradisiacal island of Vieques, billed as the Caribbean's next major tourist destination. However, not everything here is as it seems, as Simon examines the impact six decades of bombing and weapons testing by the U.S. Navy and Army has had on the landscape of this tiny island and on the people who live there.

Simon Reeve continues his epic journey around the Caribbean Sea. Travelling from the stunning Caribbean islands of Barbados and St. Vincent to the diverse mainland coast of Venezuela and Colombia, Simon meets the region's extraordinary people, and explores some of the issues they face.

On the Caribbean coast of Nicaragua Simon visits a remote community that could be split in two by the world's largest engineering project. In Honduras Simon dives in crystal clear water on the 'Jewel of the Caribbean', and travels to San Pedro Sula, the murder capital of the world. Inside the city's prison he meets the gang leaders largely responsible for the violence plaguing the country. And Simon finishes his Caribbean adventure on the beautiful beaches of Jamaica.