Chiado is the bookish, polished half of the upper city, and Bairro Alto is its scruffy nightlife twin one street over — but go by day and the whole thing becomes a quiet literary walk. Two and a half kilometres, best in the afternoon, before the bars open and the character changes.
Start at Livraria Bertrand, the oldest bookshop in the world still trading, open since 1732. A few doors up, A Brasileira, the café where Pessoa and the poets sat — he's bronze on the pavement now, and everyone queues to sit beside him. Then up to the Convento do Carmo, the Gothic church the earthquake unroofed and the city never rebuilt: bare arches open to the sky, the most affecting ruin in Lisbon.
Cross into Bairro Alto while it's still asleep — shuttered, catted, hosed-down, far better than its night self. Climb to Miradouro de São Pedro de Alcântara, the formal little terrace with the castle laid out across the valley and a quiosque (a garden kiosk-café) for a drink.
End on the Elevador da Bica, the toy yellow funicular down the steepest street in the city, to Cais do Sodré and the river.
