A stroll around Watsons Bay will take you to numerous historically significant sites and locations.

The original Aboriginal inhabitants of what is now Watsons Bay were the Gadigal People, who referred to the area as Kutti. The Gadigal people fished, collected shellfish and launched canoes in the bays and waters around South Head. Sadly, most of the Gadigal rock engravings on cliff faces and rock surfaces have eroded.

Near the exit of Watsons Bay wharf is Robertson Park, named for the former Premier of New South Wales, Sir John Robertson, whose 1834 house Clovelly was located in the park area. To the south of Robertson Park is Dunbar House, which started life as a private residence but was later turned into a hotel with a menagerie in the gardens. Dunbar House is now a popular venue for weddings, parties and functions.

The famous Doyles on the Beach restaurant on Marine Parade is the successor to the small tea rooms first established in 1885 by Alice Doyle's grandparents.

Green Point, the promontory at the north of the bay, was a prominent landmark for early harbour navigation. Watsons Bay's first land grant to Edward Laing comprised what have become the core streets of the suburb. Numerous nineteenth- and early twentieth-century weatherboard frontages have been retained in these streets alongside homes built and renovated over the past one hundred years.

Just below Green Point is the former Marine Biological Station, built in 1881, and later used for military accommodation. It is now a Harbour Trust property periodically open to the public.

Camp Cove, now a popular swimming spot, was the site of the first landing in Sydney Harbour in 1788. An expedition party led by Philip camped there overnight before continuing on to what was to become Sydney Cove. Later pilots and a lifeboat were based there.

The path from Camp Cove to South Head reaches Hornby Lighthouse. Evidence can be seen her of military fortifications dating from the 1850s to World War II, with military activity continuing today in the form of the HMAS Watson naval base.

Thousands of visitors to Watsons Bay go the The Gap for its spectacular views of the ocean and surrounding landscape. Sadly, it is also a notorious location for real and fake suicides. Late twentieth-century revegetation and rehabilitation has restored natural bushland to the area near the Gap that was denuded by grazing stock and the cutting down of trees for timber.

Alongside The Gap is the anchor of the Dunbar which famously ran ashore here in 1857. Following the cliff top further south are more fortifications and the Signal Station. Beyond it is Macquarie Lighthouse, long a visible landmark from both far out to sea and from many vantage points around Sydney.

View of the Heads at the entrance to Port Jackson
by Joseph Lycett, 'Views of Australia', 1824