Rose Bay to Watsons Bay
This is a walk that offers a lot of variety. Catch a ferry from Circular Quay to Rose Bay Wharf. From there walk along the shoreline to New South Head Road and past all the shops. Head up the hill and turn left into Tivoli Avenue, and then left at Bayview Hill Road, until you come to the end.
A marked path takes you onto The Heritage Foreshore Walk. It's a 1.5 kilometre walk through bushland, with fantastic views down the harbour to the city. There are stairs and boardwalks, but designed for most walkers. Secluded beaches are located at Hermit Point and Milk Beach. Heritage-listed Strickland House overlooks Milk Beach. The walk ends at Nielsen Park, where Shark Beach has a netted swimming zone . The Nielsen Park Kiosk provides lunch and drinks.
Continue on from Nielsen Park to Vaucluse Road, then along Wentworth Road past Vaucluse House. A right at Chapel Road and a left at Fitzwilliam Road takes you to a pathway down to Parsley Bay. Cross the footbridge there, climb the hill and turn right into The Crescent, then left into Hopetoun Avenue. Follow the road past the many glorious homes of Vaucluse.
A left at Robertson Place will take you to Watsons Bay. Behind the ferry wharf, Robertson Park has an old world feel about it and is perfect for a picnic under the trees. There are numerous restaurants including Doyle's On The Beach, Dunbar House and Watsons Bay Beach Club. Regular ferries travel back to Circular Quay.