In the first episode, Trevor visits the biggest island, Cuba, and learns about life under a communist regime. Life is like a time warp in the Castro-led country and nearly everything is 50 years old - including the cars. Food is rationed, a TV can cost more than a house and everyone is paid equally from doctors to taxi drivers.

In the second part of his journey, Sir Trevor discovers three parts of the Caribbean which all have one thing in common – they are all defined by money. • He visits Barbados, a luxury haven for the rich and famous, and the home of one man who is so wealthy he owns much of the island. • He travels to poverty-stricken Jamaica, a country blighted by violence and drugs, and meets the British girls who have been jailed for drug-smuggling and the local women trying to turn their lives around through music. • And his first stop in the second programme is the Bahamas – the wealthiest outpost of the Caribbean where many of the 700 islands have been bought by rich foreigners.

In this final episode Trevor visits Harbor Island in the Bahamas, Grenada and Montserrat. Montserrat was once an island paradise where many of the biggest stars in the world came to record hits at George Martin's famous Air Studios. Trevor meets the legendary Beatles producer as they return to the studio where Dire Straits recorded th