Navigating the Internet of Things is an exploration of interconnected objects, functions, and situations in networks created to ease and manage our daily lives. The Internet of Things represents semi-automated interconnections of different objects in a network based on different information technologies. Some examples of this are presented here in order to better understand, explain, and discuss the elements that compose the Internet of Things. In this chapter, we provide a theoretical and practical perspective on both the micro- and macro-scales of ‘things’ (objects), small and large (e.g. computers or interactive maps), that suggest new topographic relationships and challenge our understanding of users’ involvement with a given technology against the semi-automated workings of these systems. We navigate from a philosophical enquiry into the ‘thingness of things’ dating from the 1950s, to the idea of the supposed ‘smartness’ of new technologies today – and back again – as we ask questions to alert us to the kinds of tensions these elements may impose on our lives and on our ability to understand the world around us today, and in the future