Between 1841 and 1843, Danish philosopher Soren Kierkegaard left his fiancée, traveled to Berlin twice, and wrote three groundbreaking works. His personal reflections on travel amid love and loss gave way over time to a complex conception of Christian faith as an unremittingly taxing journey to reconcile, overcome, and even incorporate opposing forces such as doubt and despair. With particular attention to Fear and Trembling (1843) and The Sickness Unto Death (1849), I will consider developments and continuity in Kierkegaard's use of travel imagery. I hope to contextualize his innovative and challenging conception of faith.