This 3-4 hour walk is a wonderful way to view the North and South headlands of Sydney Harbour. I recommend taking the bus to Spit Bridge in Mosman and getting off at the stop just before the bridge (Don't bother parking in the public car park at Spit Bridge as the parking fees are obscenely high, especially on the weekends!). Then walk northwards over the bridge and walk down the roadway to the water's edge. Then head east and follow the signs on the well-marked trail. You'll see million-dollar houses, million-dollar views and lovely bush over the next few hours.
Take a picnic (maybe a bottle of wine) and a water bottle for the hike and sit out in the national park gazing out into the Harbour, through the headlands to the South Pacific Ocean. You won't think that you are only a few kilometres from the heart of a major international city :-)
It is better to finish your hike in Manly because then you can enjoy its beaches, cafes, pubs, jazz festival (September usually), etc.
Then take the 30-minute ferry ride back to Circular Quay to end a lovely day!
If the previous week has been sunny, then joggers are all that is required, however if you are doing this hike just after / during rain, you'll benefit from hiking boots.
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