Wandering the coloured cerros — Valparaíso's magic is the hills — a chaotic, vertical maze of houses painted every colour, corrugated iron and faded grandeur, threaded by staircases, alleys and hidden passages, with the Pacific glinting below at every turn. Cerro Alegre and Cerro Concepción are the classic, most walkable pair, full of murals, mirador viewpoints and cafés. There's no set route; the pleasure is getting pleasantly lost, climbing and descending, finding the next painted wall, the next view, the next cat on a wall. It's the essential Valpo experience.
Funiculars and the port — Linking the flat lower town to the hills are Valparaíso's antique funiculars (ascensores) — creaking, century-old cable lifts that haul you up the near-vertical slopes, a beloved and characterful way to climb (several still run). Down in El Plan, the port and Plaza Sotomayor hold the maritime heart — the naval monument, the boats, the markets. Ride a funicular up for the view and down for the port, and you've grasped the city's up-and-down geography and its seafaring past.
Street art and the bohemian spirit — Valparaíso is one of the great street-art cities of the world — its walls, stairways and houses are covered in murals, from vast painted façades to tiny stencils, a living, ever-changing open-air gallery (Cerro Bellavista's open-air museum and the lanes of Cerro Alegre are the hotspots). This artistic, bohemian identity runs deep: the city was beloved of poets, above all Pablo Neruda, whose quirky hilltop house La Sebastiana, with its bay views, is a wonderful museum. Between the murals, the poetry and the cafés, the creative spirit is Valpo's soul.
Seafood, wine and the coast — Valparaíso eats well and cheaply — Chilean seafood from the port (machas, congrio, ceviche, seafood empanadas), the hearty chorrillana (chips piled with meat, egg and onion), completos (loaded hot dogs), and the market fondas, washed down with Chilean wine or the potent terremoto. The city is the gateway to the coast — the beach-resort glamour of neighbouring Viña del Mar — and to the Casablanca and central-Chile wine valleys just inland. Between the hills and the harbour, eat the seafood, drink the wine, and enjoy the Pacific setting.