Chiado and Bairro Alto by day
The oldest bookshop in the world, a roofless Gothic church, and the grid above before it wakes up for the night. This is a Claude-drafted route awaiting the editor's walk.

1. Livraria Bertrand
Start at the oldest bookshop in the world still trading — open since 1732, a Guinness record on the wall to prove it. The Portuguese-language stock runs deep, but there's a decent English shelf too. Buy something small; it feels right to start a literary walk by funding one.

2. A Brasileira
A few doors up, the *Chiado* café where the poets gathered — Fernando Pessoa among them, now cast in bronze at a pavement table outside, where everyone queues to sit beside him. The coffee inside is ordinary and the décor is the point: art-deco mirrors, the literary ghosts. Take a *bica* (the short Lisbon espresso) standing at the counter like a local.

3. Convento do Carmo
Up the hill to the roofless Gothic church the 1755 earthquake unroofed and the city chose never to rebuild — bare arches open to the sky, the most affecting ruin in Lisbon. The small archaeological museum in the apse is worth the ticket. Go in the afternoon when the low sun comes through the empty windows.

4. Bairro Alto
Cross into the grid of narrow streets that is Lisbon's nightlife by dark and its hangover by day. Come now, in daylight, when it's quiet — shuttered bars, a few old shops, cats, the occasional resident hosing the cobbles. It's a different and better quarter before the crowds arrive.

5. Miradouro de São Pedro de Alcântara
The terrace at the top edge of *Bairro Alto* — a formal little garden on two levels, the castle and the *Baixa* spread out across the valley opposite. A *quiosque* (a garden kiosk-café) for a drink with the view. One of the great sit-down spots in the city, and free.

6. Elevador da Bica
Walk back through the grid and take the *Bica* funicular down — a tiny yellow tram on a street so steep it's almost a stair, running since 1892, the most photographed descent in Lisbon. It drops you toward the river and *Cais do Sodré* for the metro and the riverfront.

Chiado and Bairro Alto by day