Old South Head Road is a major road in Sydney, linking the eastern suburb of Bondi Junction to Watsons Bay on the South Head peninsula. It is historically significant because its earliest origins can be traced back to the early days of the colony of New South Wales.

Watsons Bay is a harbourside, eastern suburb of Sydney, in the state of New South Wales, Australia. Watsons Bay is located 11 km north-east of the Sydney central business district, in the local government area of the Municipality of Woollahra.