The Cruise presents New York City to audiences from a different perspective as seen through the eyes of a well-known tour guide. Filmmaker Bennett Miller brings his camera inside a Manhattan Gray Line double-decker bus to document and follow Tim "Speed" Levitch, as he presents the famous city to tourist and viewers at home. Tim is homeless and a self-proclaimed speaker, philosopher, author and tour guide, who uses his dynamic personality to present New York to audiences in an unusual fashion. He mixes his knowledge of New England architecture and ancient philosophy with some historical facts, as he works each day trying to make enough money to find a warm place to sleep. Tim prefers to bunk with friends or in public places because he wants to live as a free man. Bennett films the tour guide inside and outside of work, living out of his suitcase and giving the filmmaker his vision of the city throughout the film.