The comedian, musician and nature lover takes fellow comedian Alan Davies to the Peak District National Park, walking the Monsal Trail to Derbyshire's highest pub, Abney Moor and Mam Tor. These two have been friends for 30 years and Bill was Alan's best man. As they walk, they chat about the perils of ageing, the stresses of modern life and the loss of their friend Sean Lock.

Bill and broadcasting legend Sir Trevor McDonald embark on walks in Essex and Suffolk, exploring the home of the artist John Constable. Their walks take in Dedham Vale, the Essex-Suffolk border and the Stour Estuary. As they stroll, they discuss Sir Trevor's emigration to the UK from Trinidad, his long and esteemed career as a journalist and some of his most memorable interviews, including Nelson Mandela.

Bill walks with comedian and writer Paul Merton along the Jurassic Coast on the Southwest Coast Path in Dorset. Together, the men discuss the question of what we leave behind as Paul ponders a return to life as a touring stand-up and opens up about his mental health.

Bill meets with Shaun Ryder in Somerset for walks around the Avalon Marshes, Chew Valley Lake and Ham Hill. Along the way they discuss Shaun's life of rock and roll excess, being diagnosed with ADHD late in life and his return to music.