Sydney's harbour is the reason it exists. The First Fleet arrived in 1788 and chose the sheltered cove where the city stands, on land long cared for by the Gadigal people of the Eora nation. The Harbour Bridge, opened in 1932 and known to everyone as the coathanger, and the Opera House, whose white sails by the Danish architect Jørn Utzon were completed in 1973, have since become the pictures people carry in their heads. In reality both look better when you stand under them at dawn, with the ferries just starting up and the water gently moving.
The Grand Pacific Drive begins here, and the sensible way out is south. Leave the centre early on a weekday or Sunday morning, avoid the rush hours, and follow signs through the southern suburbs toward the Royal National Park, which is the second oldest national park in the world, dating from 1879. The road winds through bushland and eucalypt forest with views over the Tasman Sea, and then continues past Stanwell Tops, where hang gliders launch over the cliff. After that comes the Sea Cliff Bridge at Coledale, a curved concrete viaduct built out over the water along a stretch of coast where the old road kept falling into the sea.
Take the traffic seriously. Sydney is a big, busy city, and the tollways around it are electronic, so check how a hire or foreign-registered bike will be billed before you set off. Lane filtering is legal for riders in New South Wales under defined conditions, but local rules are strict and the speed cameras are many, so read up before you rely on it. Summer brings heat, bushfire smoke in bad years and afternoon storms, and the best months for the coast are April to May and September to November.
The city offers everything a rider needs, with fuel at countless stations and workshops for every brand. Spend an evening at the water's edge near Circular Quay, take a ferry across to Manly if you have time, and have a flat white from one of the city's many small roasters. Then the coast road will be waiting.