Exploration of the Sydney area by the early European settlers brought them into contact with the local Aboriginal people, the Eora.

As Tim Flannery says in The Birth of Sydney:

"Ever since the end of the last ice age the waters of Botany Bay and Sydney Harbour have provided a living to Aboriginal people. When the British arrived its bays and coves were dotted with Eora canoes, and the smoke of Eora campfires filtered from its caves and rock shelters. Women paddling fragile canoes even ventured outside the Heads on fishing expeditions. Governor Phillip estimated that about 1500 Eora lived in the area between Botany Bay and Broken Bay. Some of those living on the northern shores of Sydney Harbour called themselves Cadigaleans, for Cadi was their name for Sydney Harbour, and galeans means 'the people of'."

The harbour acted as a sort of dividing line between two Aboriginal groups, the Camerigal who lived between Botany Bay and the south shore, and the Cadigal, who largely dwelt between the north shore and Broken Bay. As with most neighbours, relations between the two groups seem to have alternated between feasting and fighting. The opportunity for a feast came only rarely to the Eora, for it was difficult to find sufficient food to satisfy a large group for any length of time. A gift from the sea in the form of a stranded whale seems to have offered the most common opportunity. The discoverers of a stranded whale would light fires to broadcast news of the discovery, and then people would converge for days of feasting."

"On the south side of the harbour entrance lies South Head, and behind it a great sweep of sand backed by grass and stately Port Jackson figs. This is Watsons Bay, which has long offered the most sublime views of the city. The trip out along Old South Head Road, the first road built in the colony, was a favourite weekend jaunt in the early days and a compulsory sightseeing expedition for distinguished visitors who could then admire the city's lighthouse.

Proceeding along the southern shore we come to Rose Bay where Bungaree, the first Aboriginal circumnavigator of Australia and 'King of Sydney', was buried in 1830. Further on is Point Piper, where Captain Piper, the celebrated 'Prince of Australia', built his magnificent residence which was so favourably commented upon by many new arrivals.