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What season is best to travel around Australia?

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We are two couples, in our late fifties, planning to travel around Australia in a Winnibego or car + B&B's for 4 months. AS one of us is a teacher, she would like to start in August or September. Some of us would like to start in January. Planning to start in Sydney as we all have family there, Clockwise or anti clockwise? Advice please! Positive and negative!

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