One of Madrid's most atmospheric squares, Plaza Santa Ana sits at the heart of the old literary quarter where Cervantes, Lope de Vega and Calderón de la Barca all lived and worked. Statues of Calderón and García Lorca watch over the terraces.
The square itself is lined with classic Madrid bars. Cervecería Alemana, a favourite of Hemingway's, still pulls cold beers on the corner. Villa Rosa, with its gorgeous tiled facade, has been a flamenco venue since 1914. The Viva Madrid bar around the corner is worth stepping into just to see the azulejo-covered interior.
Come in the evening when the terraces fill up and the tapas crawl through the surrounding streets — Calle Echegaray and Calle Ventura de la Vega are both within easy walking distance and packed with options.