This lecture explores the Holyhead Road as a cultural corridor along which people, books, and ideas move, and is part of a larger project examining infrastructural links as sites of cultural exchange between Britain and Ireland from Swift to Joyce. The lecture begins by following Buck Mulligan's invitation in the opening of Ulysses to 'come and look' at the sea, and at the mailboat crossing from Kingstown to Holyhead. Looking at the sea takes us to questions of boundaries and connections, to the local, national, and global scales of identity and belonging, and to the contested and diverse meanings of routine journeys between Ireland and Britain. The representation of different aspects of this route by Katharine Tynan, W.B. Yeats, Sean O'Casey, Thomas Kinsella, Emyr Humphries and R.S. Thomas highlights the affective dimensions of the crossings and journeys made through Ireland, Wales and England, and suggests the lines of influence, connection, and contest that travel along these transport routes.