Time Out says
This ten-kilometre trek is best approached from Spit if you want to reward yourself with snacks at the finish line
The route takes you from sandy coves to beautiful vantage points of Sydney Harbour, up and down rocky staircases, and to at least four secret beaches.
You’ll need to keep an eye out for the signs, but at the highest point of the climb you can see Aboriginal rock engravings of a kangaroo, a whale and small fish at Grotto Point. Castle Rock beach is postcard perfect, so bring your swimmers and a towel as you’ll want to spend time by the crystal-clear water at the otherwise hard-to-reach beach in Middle Harbour.
Should you pack snacks? Definitely bring water and proper sun protection, as there are very few water fountains and limited shade. However, you may want to make a day of it with lunch at Queen Chow in Manly or Chiosco by Ormeggio, a short walk over Spit Bridge.