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.
On a shopping trip with local journalist Juan, Sir Trevor discovers that his monthly shop comes to $2 thanks to getting items at a subsidised rate, but as consumerism is discouraged by the government they place taxes on items we take for granted, like toasters.
Trevor notes: "The entire city is enveloped by a sense of faded elegance. Buildings once grand and magnificent show signs of weary neglect."
In stark contrast, Sir Richard Branson's Necker Island couldn't be more different. The Virgin boss takes Sir Trevor on a tour of the place he purchased in the 70s. He bought the beautiful but unihabitated island and turned it into a luxury paradise, where the super rich shell out ?30,000 a night to enjoy the surroundings.
Finally, Trevor returns to his native home of Trinidad and arrives at of the country's annual highlights - a two-day long carnival.
He gets to meet the dancers and the man who hand crafts the steel drums which are sold all over the world. And he even gets dolled up in one of the elaborate costume - now that's got to be worth a look!
Feeling nostalgic Trevor says: "Watching the festival this year brought back for me a flood of warm memories. For two days Trinidadians put all their problems behind them and lose themselves with abandon in a riot of noise and colour."
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