Herbert Boyes was born in Launceston on 15 November 1917 and was raised on Flinders Island, where he attended Whitemark School. He was the son of a highly respected boatman renowned for his extensive knowledge of the Furneaux Group waters. Before enlisting, Herbie worked in a variety of occupations on the island. On 30 December 1941 he enlisted in the Australian Army alongside his brother Harry, the two brothers receiving consecutive service numbers, TX6573 and TX6574. During the Second World War Herbie served in Anti-Tank Regiments and later with Water Transport units in New Guinea and the Islands before being discharged in May 1946.

After returning to Flinders Island, Herbie married Joan, herself a Second World War veteran.

Joan grew up in Manly, Sydney and was stationed in Sydney serving with the Women's Royal Australian Naval Service (WRANS) as a transport driver, meeting Naval ships and seeing them off. After the war, Joan moved to Launceston, then in 1946 applied for a job on Flinders Island, working as a school bus driver and bookkeeper. Herbie lived not far away.

The couple moved onto Lot 2 Whitemark Estate in 1952, the first soldier settlers to move onto a farm with this scheme.  They established a dairy farm, where Herbie milked around sixty cows for many years until the factory closed in 1974. They then converted the property to mixed beef cattle and sheep production while the family raised their six children.