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In a revealing and emotional journey, Lenny Henry travels to the Caribbean to investigate his own heritage and the relationship between the Commonwealth, the Caribbean and the UK.

Lenny's life would be very different without the influence of the British Empire and the Commonwealth. Because of the relationship between Jamaica and Britain, his parents were able to move to Dudley in the 1950s, putting Lenny on the path to fame and fortune in the UK. Lenny examines the deep-rooted and complicated connection between the Caribbean and Great Britain, and the role the Commonwealth now plays in this relationship. Where did this organisation, made up of 53 countries and 2.3 billion people, come from? How can it survive its legacy of empire and slavery? Does it have any role in the 21st century?

Lenny sets off on a tour into the body, mind and soul of the Caribbean, to investigate the experiences of those who live so far from the UK but remain members of this vast and populous club. He travels back to Jamaica to investigate his own beginnings and finds out why, 60 years ago, his mother uprooted the family to travel thousands of miles to the rainy Midlands. He meets his older brother Seymour for a tour of the remote and rural plot he would have called home if the Henrys had remained on the island. He visits a lush rum plantation in an attempt to understand what life was like for his ancestors - African slaves brought to the Caribbean against their will. Lenny spends time with Commonwealth champion Rasheed Dwyer and Olympian Sashalee Forbes, and hangs out at a Chronixx gig to hear what importance, if any, the Commonwealth has to Jamaicans today.

In Antigua, Lenny traces the roots of why the British ended up in the Caribbean in the first place and meets some of the expats who have decided to make the Caribbean their home. Finally he travels to Barbuda to visit the island community devastated by Hurricane Irma, to hear tragic tales from survivors and consider the role the Commonwealth could play in the future around the world.

Meeting a collection of real people along the way - street vendors and historians, teachers and students, entrepreneurs and politicians, as well as members of his own family - Lenny examines the special bond that exists between the people of the Caribbean and the UK, a microcosm of the wider relationship between all of the people of the Commonwealth.