Centenaries, bi-centenaries, and similar milestones are occasions to reflect upon people, events, institutions. 2015 was the year that brought together two major authors born in the same year, one hundred and fifty years ago – W.B. Yeats and Rudyard Kipling – both with connections with India, although in two entirely different ways. Reading milestones is a temptation to dwell on the moment, on uniqueness and on individual achievement. What I wish to do here instead is to open up the perspective. Milestones are part of a process and that process is a journey. I would like to suggest that the very notion of a journey is central to the ways in which Yeats and Kipling wrote their finest poetry. Their individual modes of interweaving this concept into their poetry are an index to both their similarities and their differences.