The Manly Scenic Walkway
This was a lovely walk, I think I heard about it through the Lonely Planet. After some searching around for the right bus, which takes you over the Sydney Harbour Bridge the bus driver stopped for me and told me where to start the walk (very friendly).
At first you walk over the bridge (or can get off at the other side, but I wanted to have a look) and are hit by the huge, expensive looking houses!
The walk is well sign posted throughout and you go buy some lovely secluded beaches, very tropical looking, you get wonderful views when you get up high of the city and the coastline, and all the boats bobbing around.
I passed some big lizards and the odd small snake, at the highest point there's some Aboriginal rock carvings to see, you can see why they carved them where they did; spectacular views.
You end up on the far side of Manly, a secluded fishing area then walk around to the main part.
It is 9kms and takes around 3-4 hours, be sure to take plenty of water and your bathers! Watch out for sharks, I read there's not been an attack for 35 years, but they could happen as around most of Australia.
If you don't want to walk back you can hop on the ferry to Darling Habour, make sure you get a nice cold beer on the Manly side first and watch the sun go down, as I did!
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Website: http://www.openroad.com.au/travel_onfoot_thespittomanly.asp