‘What is this place?’ – A deviously simple question asked by a cruise-ship passenger on a half-day tour to Paldiski. The question can be asked anywhere at any time but this specific one at this specific moment and location triggered a deeper exploration of this particular place. The answer surely depends on who you are, who you ask from, what are your previous experiences of places and what are your expectations of this one. A place is many things, a pattern of implicit and incomprehensible features, or is it a place at all? This paper is my attempt to synthesise the experience of a historical geographer examining the past of the Pakri peninsula on the northern coast of Estonia about 30 km west of its capital city of Tallinn, its ecological, social, and cultural boundedness with that of a tour guide taking unsuspecting visitors around a landscape where both the human-built environment and nature reach their respective limits. In addition, Paldiski – the port established by Peter I in 1718, a prison camp, a farming community, a Soviet military enclave from where all the maritime spy missions in Europe were supposedly launched during the Cold War, a harbour with allegedly amazing potential, or a cursed and god-forsaken town – is highly contested locally with competing strategies and political parties taking centre stage in turns. In the context of energetic imagineering and place-marketing in Estonia today, partly grounded in historical understandings but mostly in fantasy, ‘Paldiski’ is exceptional and typical and hence the broader processes and hybrid character of branding, of making a mark, of creating a heritage future, and local responses can be examined on its example.