In late 1973, sponsored by The Sunday Times, Simon began travelling around the world on a 500 cc Triumph Tiger 100 motorcycle. For four years he travelled over 64,000 miles (103,000 km) through 45 countries. Most accounts from his trip are detailed in his book, Jupiter's Travels, while some of the book's gaps are filled in its second part, the book Riding High.

From Seattle, Washington to Marysville, Ohio on a Fowler Truss frame wheel in 53 days, covering over 2,600 miles on eighty-five dollars and fifty-nine cents. That is how William Henry Sheneman spent the summer of 1896.

People .asked why we did not take a motor instead of a motor ‘sidecar. They were extra-ordiriarily fertile in recommending makes of motor-cars. And I had to explain that - yes, we have no motor-car - no, we belong to the fraternity of vagabonds.

Sheridan, Clare. Across Europe with Satanella. New York: Dodd, Mead and Company, 1925.