All harbourside walks outlined here are featured in detail in an excellent book called Walking Sydney, which sells in Sydney bookshops for around $AUD22. The book has 25 walks (complete with maps) around Sydney Harbour, historic areas of Sydney and the surf-beach suburbs.
Watsons Bay / The Gap
Perphaps the most spectacular harbourside walk is one that starts at The Gap, a spectacular ocean cliff at Watsons Bay, near South Head, winds its way down through Vaucluse, meanders through Watsons Bay and takes you all the way up to the lighthouse at South Head. The Gap is famous not so much for its natural scenic beauty, but for more bizarre reasons: a reported 20-30 people suicide each year by leaping from The Gaps on to the rocks below. Dozens slip from the rocks, which makes it a dangerous place to be if you don't keep to the paths and stay behind the barriers.
What makes this walk so good is that you gain a great perspective on the positioning of Sydney Harbour in relation to the ocean. One you reach South Head, you can see the entrance to the harbour, North and Middle Heads and the main harbour channel leading up towards the city. Before you reach South Head, you get to pass Camp Cove and Lady Beach, some of the most picturesque and idyllic small beaches anywhere in the world.
If you can only spare the time to do one harbourside walk, this is the one to do.
Virtual Tour of the Sydney Coast
Justin Sullivan presents an online tour of parts of the Sydney coast he finds interesting.
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