In this chapter, the author shares his experiences with a group of people who were also novice urban explorers, climbing the stairs inside the Woolworth Building in Manhattan, one of the city's most iconic buildings and the world's first ever skyscraper, less than two blocks and half a mile away from where Phillipe Petit performed his tightrope walk. He felt anything but, his eyes flitting between the strangers he had just met that he was exploring with and the other strangers in the lift who presumably had no idea about what authors were doing. Craning his head up, he saw 30 floors of red metal stairs, zigzagging up into a vertical vanishing point. By operating at the boundaries of the city's institutions, they had glimpsed a De Certeauian view of Manhattan from a vantage point that few people would ever get to see, particularly since the destruction of the World Trade Center's observation decks on 11 September 2001.