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The oldest part of Sydney's settlement, the Rocks was inhabited by the first fleet of convicts arriving in Sydney Cove in 1788, impacting forever the way of life of the local indigenous people and setting the foundations for what would become an intriguing and cosmopolitan city.

Heading out aboard a twenty metre long, motorised catamaran from Sydney's aptly named Darling Harbour, the refreshing breeze will clear the cobwebs as you pass between the North and South Headlands and into the open water.