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Watkin Tench was a naval officer who embarked in 1787 on the first British fleet conveying prisoners sentenced to be transported to Australia. Watkin Tench kept a diary that was published in two volumes in London in 1789 and 1793. The diary recounts a remarkable “colonial encounter”: the confrontation of an Aborigine group, convicts, seamen and officers of the Royal Navy in a context of extreme isolation and shortages on the shores of Port Jackson. The article relates, through the eyes of a member of the educated elite in the Enlightenment period, a two-way discovery of radical foreignness, of the Aborigine Indians, on the one hand, and of the convicts on the other, testifying to the unusual colonial experience which laid the foundations for contemporary Australia.