The perfect combination of stunning views and bushy terrain through Sydney Harbour National Park in North Sydney. One way, the route spans about nine kilometres, but the 18 km out-and-back is really worth it. At Dobroyd Head, the highest point of the trail, you can enjoy nearly 360-degree views of Sydney. If you’re lucky, you might spot a whale. You can start at Manly Beach or the Spit Bridge. If you only want to go one way, bus to the Spit and catch one of Sydney’s famous ferries back to the city from Manly. The ride, with the wind in your hair and the views around the headland of the Opera House to the Sydney Harbour Bridge, is incredible.