The conference theme ‘Looking at the world history of planning’ is echoed in a statement by U.S. urban designer Edmund Bacon on the 1911 Plan for Canberra, which he eulogized as ‘a Statement of World Culture’.1 Bacon was referring to the way in which the Griffins’ plan incorporated elements of space design derived from cultural realms as wide-ranging as those of Europe, the Americas, and Asia. However, the plan and its transformation in modern and post-modern times have also been objects of fundamental cultural controversies.2 Enthusiasts and opponents have dug in their heels and fought battles of uncertain outcomes. The core research question here is how to deal with the complex and controversial nature of these perspectives. In this situation, the paper applies the famous ‘Windows’ metaphor from the preface of Henry James’ novel ‘Portrait of a Lady’ as a narrative device to the context of planning history.3 It concludes that the windows opened upon ideas and realities, myths and models surrounding the Canberra Plan and its transformations may help negotiate between opposing views, different paradigms and conflicting cultural positions as potentially complementary and at least enlightening