FATMAP difficulty grade
Starting from Raleigh Reserve this trail moves north along the Dover Heights cliff line, up Weonga Rd where you will find beautiful harbour views and back down to the cliff line at Lancaster Rd.
From there you simply follow the path around past Diamond Bay, the Light House and down to The Gap and Watsons Bay.
If you're feeling like it, I suggest you continue to Camp Cover and around South Head past Hornby Light House and return to Watsons Bay for a well earnt drink.
The 380 bus will return you to Raleigh St if you run one way.