I challenge you to find a more fulfilling circuit that not only works out your body but also your camera, with striking vistas of the city skyline amid lush foliage.
With the sun out, a spot of lunch is best enjoyed at the water's edge in Darling Harbour and Cockle Bay. And take the opportunity to savour the elevated city perspective of the Sydney Monorail one last time, as it will literally reach the end of its line when it's decommissioned on June 30.
Another fabulous Sydney experience is to board a ferry at Circular Quay for the 10-minute ride to leafy, historic Balmain. The harbour enclave is one of Sydney's oldest suburbs, settled by boatbuilders in the 1830s. It's where most of Sydney's iconic yellow and green ferries were built.
Balmain is now a thriving artistic suburb, home to some of Australia's best-known writers, actors and musicians. The main thoroughfare of Darling St is a melange of sandstone cottages and wrought iron-wreathed villas, galleries, boutique stores and historic pubs. Quench your thirst with a foam-topped lager from the sprawling balcony of the London Hotel, one of the city's most atmospheric pubs.
If you want to scratch even further beneath the surface of the inner city, head to Newtown and Paddington to rub shoulders with the edgy and eccentric locals.
Enmore Rd and South King St are home to vintage fashion stores and a billowing array of specialised curio stores. Buttons, beads and tiles are big in Newtown.
Paddington's status as an antiques mecca is legendary, but accentuating its allure is the biggest concentration of Sydney's most beautifully restored Victorian terraces, replete in cast-iron latticework.