Jeanette Winterson's novel Sexing the Cherry is a story about the Dog Woman and her adopted son Jordan, who live in seventeenth-century London. After meeting John Tradescant, a famous botanist and gardener, Jordan, who was found in the Thames and named after the Jordan River, becomes obsessed with travelling, exploration and discovery. He accompanies Tradescant on his journeys across the world in search of exotic plants. At the same time, Jordan does a lot of daydreaming and mind-travelling. On these journeys, which he finds equally realistic and important, he visits magical cities and meets fairy-tale characters. Besides, since Jordan and his mother have their twentieth-century counterparts, it can be said that they also travel through time. This paper will explore the different ways of travelling described in this novel with the purpose of discovering to what extent it follows the conventions of the travel genre in general. It will also examine travelling in the context of the Enlightenment period and colonial expansion of the British Empire. In addition, since one of the novel's most significant topics is gender roles, this paper will also focus on the differences between male and female travellers, and male and female time.