This epic walk has two major components: the 10km western stretch between Manly and Spit Bridge, and the 9.5km eastern loop around North Head. Either download a map or pick one up from the information centre near the wharf.
The western section traces the coast past million-dollar harbour-view properties and then through a rugged 2.5km section of Sydney Harbour National Park, which remains much as it was when the First Fleet sailed in. After crossing the Spit Bridge you can take a bus either back to Manly (buses 140, 143 or 144) or into the city (176 to 180).
The eastern loop is known as the North Head Circuit Track and takes between three and four hours. From the wharf, follow Eastern Esplanade and Stuart St to Spring Cove, head into the North Head section of Sydney Harbour National Park, and make your way through the bush to the spectacular Fairfax Lookout on North Head (approximately 45 minutes in total). From the lookout, walk the Fairfax Loop (1km, 30 minutes) and then head back via the Cabbage Tree Bay Walk, which follows the sea-sprayed shoreline back to Manly Beach via picturesque Shelly Beach and tiny Fairy Bower Beach.