Signal Hill Battery

The Dunbar was a full-rigged ship designed and built from 1852 to 1853 by James Laing & Sons of Deptford Yard in Sunderland, England and used for maritime trade, as a troop ship and transport. The Dunbar was wrecked near the entrance to Sydney Harbour, Australia in 1857 with the loss of 121 lives. The wreck of the Dunbar ranks as one of Australia's worst maritime disasters, with the event still retained in the social history of Sydney and New South Wales. The location of the wreck is now a heritage site, at Watsons Bay. An anchor from the Dunbar, a memorial and remains of the 121 onboard are located within Camperdown Cemetery. The property is owned by the NSW Land Registry Services. The site was added to the New South Wales State Heritage Register on 17 October 2003. The Australian National Maritime Museum holds the John Gillies Collection of artefacts from the Dunbar wreck.

Alexandria Parish is one of the 57 parishes of Cumberland County, New South Wales, a cadastral unit for use on land titles. It contains the area to the south and east of Sydney city including Bondi, Paddington and Clovelly. It was probably named after the Battle of Alexandria fought in 1801. The Parish of Alexandria roughly corresponds with the "Eastern Suburbs" in the traditional narrow sense of that term. The "Eastern Suburbs" in a wide sense also includes the suburbs immediately to the south, in the Parish of Botany.

The Macquarie Lighthouse, also known as South Head Upper Light, is the first, and is the longest serving, lighthouse site in Australia. It is located on Dunbar Head, on Old South Head Road, Vaucluse in the Municipality of Woollahra local government area of New South Wales, Australia. The lighthouse is situated approximately 2 kilometres (1 mi) south of South Head near the entrance to Sydney Harbour. There has been a navigational aid in this vicinity since 1791 and a lighthouse near the present site since 1818. The current heritage-listed lighthouse was completed in 1883. The lighthouse and associated buildings were designed by James Barnet and built from 1881 to 1883. The lighthouse is fully operational and is under the control of the Australian Maritime Safety Authority. The grounds are managed by the Sydney Harbour Federation Trust.The lighthouse is featured on the coat of arms of Macquarie University. A simplified line drawing of the lighthouse forms the logo of Woollahra Council in which local government the lighthouse is located. The lighthouse and associated site were added to the New South Wales State Heritage Register on 2 April 1999 and to the Commonwealth Heritage List on 22 June 2004.

Caroline Byrne (8 October 1970 – 7 June 1995), an Australian model, was found at the bottom of a cliff at The Gap in Sydney in the early hours of 8 June 1995. Her then boyfriend Gordon Eric Wood (b. 1962), who at the time of her death was a chauffeur and personal assistant to businessman Rene Rivkin, was convicted of her murder on 21 November 2008 and spent three years in Goulburn Correctional Centre. He was acquitted of the conviction in February 2012.

The Gap is an ocean cliff at South Head in the Eastern Suburbs of Sydney, Australia. The area, which faces the Tasman Sea, is located in the suburb of Watsons Bay. Although the cliff is a popular tourist destination, it has an infamy for suicides.

Doyles on the Beach is an Australian seafood restaurant founded in 1885. Located on Marine Parade in Watsons Bay, Sydney, it is Australia's oldest continually running fish and chip shop, currently owned by Michael Doyle. There is both an à la carte restaurant and a garden bar at the Marine Parade establishment. It has two sisters restaurants: Doyles Fishermans Wharf, also in Watsons Bay, and Doyles at the Sydney Fish Market.In 2021, the restaurant was named in GQ's list of the "18 most expensive restaurants in Australia".One of the restaurant's attractions is the view over Sydney Harbour of the downtown Sydney skyline four miles to the east.

Watsons Bay ferry wharf is located on the southern side of Sydney Harbour serving the Sydney suburb of Watsons Bay.

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. Watsons Bay sits on the end of the South Head peninsula and takes its name from the sheltered bay and anchorage on its western side, in Port Jackson (Sydney Harbour). It provides views across the harbour to the Sydney Harbour Bridge. The Gap is an ocean cliff on the eastern side with views to Manly at North Head and the Pacific Ocean. Vaucluse is the only adjacent suburb, to the south.

The South Head General Cemetery is a heritage-listed cemetery located at 793 Old South Head Road, Vaucluse, New South Wales, Australia. It was built from 1845 to 1950. It is also known as Old South Head Cemetery and the South Head Cemetery. The property is Crown Land governed by Waverley Municipal Council. It was added to the New South Wales State Heritage Register on 25 August 2017.

Vaucluse High School (VHS), formerly known from 1960 to 1981 as Vaucluse Boys' High School (VBHS), is a former public co-educational secondary day school that was, until its closure, located in Vaucluse, an eastern suburb of Sydney, New South Wales, Australia. In 2006 the school was merged with Dover Heights Girls High School to form the Rose Bay Secondary College.

Wentworth Memorial Church is a heritage-listed former Anglican church building located at 32B Fitzwilliam Road, Vaucluse, Sydney, Australia. It was designed by Clarke Gazzard and Partners and built by Monteith Constructions, with Miller Milston and Ferris as engineers. The property is privately owned; and was formerly owned by the Anglican Diocese of Sydney. It was added to the New South Wales State Heritage Register on 25 September 2012.

Wentworth Mausoleum is a heritage-listed mausoleum located at 5 Chapel Road, Vaucluse in the Municipality of Woollahra local government area of New South Wales, Australia. It was built from 1872 to 1874 by Mansfield Brothers, architects. It is also known as Wentworth Mausoleum and site. The property is owned by Anglican Church Property Trust and is managed by Sydney Living Museums as part of Vaucluse House. It was added to the New South Wales State Heritage Register on 2 April 1999.