Moss won the Nassau Cup at the 1956 and 1957 Bahamas Speed Week. Also in 1957 he won on the longest circuit ever to hold a World Championship Grand Prix, the 25 km (16 mi) Pescara Circuit, where he again demonstrated his mastery of long-distance racing. The event lasted three hours and Moss beat Fangio, who started from pole position, by a little over 3 minutes.
In 1957, Moss published an autobiography called In the Track Of Speed, first published by Muller, London. In 1963, motorsport author and commentator Ken Purdy published a biographical book entitled All But My Life about Moss (first published by William Kimber & Co, London), based on material gathered through interviews with Moss. In 2015, when he was aged 85, Moss published a second autobiography, entitled My Racing Life, written with motor sports writer Simon Taylor.
Moss was married three times. His first wife was Katie Molson; an heir to the Canadian brewer Molson. They were married in 1957 and separated three years later. His second wife was the American public relations executive Elaine Barbarino. They were married in 1964 and divorced in 1968. Their daughter Allison was born in 1967. His third wife was Susie Paine, the daughter of an old friend. They were married from 1980 until his death in 2020. Their son Elliot was born in 1980.