Sydney
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Sydney is Australia's biggest city.
Going South
There are two options.
The Princes Highway is more scenic and mostly not a freeway, but it's 200 km longer. You can try to take a train to Waterfall and walk to the highway. It might not be legal to stand there, though, and it's not a great spot. Guaka and amylin waited 10 minutes, declined a ride to the next town and then waited an hour or so. So possibly find yourself a better spot to start.
Take the Hume Highway if you're in a hurry (which you shouldn't be).