Lots of cyclists ride in the areas around Watsons Bay, Dover Heights and Vaucluse and why not, the sights up the bay and down the cliffs are fantastic. But its all roads and there are people driving around. To minimise your risk you can ride on a Sunday morning and you can take it easy. Another way is to only ride from Bondi to Watsons Bay and catch the ferry back to Rose Bay or the city.
For this trip I targeted the quiet council bike streets up to the water tower in Vaucluse. Then I rolled down to Vaucluse House on a really nice winding Hopetown Rd. After riding around Vaucluse house I then headed to Parsley Bay where I should have walked across rather than ride the roads around it. Then I hugged the harbour up to Watsons Bay with a quick trip to a hidden beach called Kutti Beach. I rolled around Watsons Bay and then turned on the turbo and went up the hill to Dunbar Head lighthouse. The best bit was the cliffs around Diamond Bay Reserve.
Very hilly, I did this on my eBike and that was hard enough.
Waverley to Vaucluse
On reflection I decided that the first part of the journey was good enough to make the tricky but not impossible classification on my maps. My trail starts at the beginning of Henrietta St in Bronte and heads across Waverley Park and down a council road into Rose Bay. Downhill is all on Birriga road and you likely will be going close to the speed of the cars anyway. On the way back up the cycle path is well marked on the side of the road with the odd section off road where the corners are tight. Its a good climb. The ride around Royal Sydney golf club into Rose Bay Village is on a tight separated cycle way. Once you are in Rose Bay, the real cyclists will head up New South Head Rd. The other way up steeper hills on back streets is the way I have mapped. At Vaucluse Water tower, you are on your own, I wont put it on my main maps.
Here are photos from this section that I took using my bike camera
The Full Trip
Do it on a sunday morning when its quiet. I won’t put this on my Sydney East map as its all roads but here is a separate map of the full trip >>
Shared Path 10%
Busy Roads 40% and not busy 50%