Chueca is the most self-assured barrio in Madrid — the neighbourhood that turned itself around in the 1990s and never lost the confidence. It's compact, social, and built around squares and a market, which makes it a near-perfect short walk: under three kilometres, all of it terraces and shopfronts, best in the afternoon when the tables fill.
Start on Plaza de Chueca, the tiled square the whole barrio orbits, then walk a block to the Mercado de San Antón — a glass market with a rooftop terrace worth the climb for the view alone. From there take Calle del Almirante for the design boutiques, cut down to Plaza del Rey and the haunted Casa de las Siete Chimeneas, then back along Calle de Augusto Figueroa, the old shoe street that still runs on sample sales.
End on the pedestrian stretch of Calle de Fuencarral, all streetwear and motion, and follow it south. Gran Vía Metro sits at the bottom — the walk drops you straight onto Madrid's great boulevard.