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In the 19th century, Valparaíso was one of South America’s richest cities, having grown fat on the shipping trade. Then the Panama Canal stole its thunder and it became increasingly dilapidated. As part of an attempt to reverse its fortunes and give it a facelift, from 2006 the local government repainted many buildings. Façades were transformed with vermilion, lime-green, puce, cornflower-blue, and mango-yellow coats. Now, Valparaíso is a polychromatic canvas awash with street art, and anything goes. It tumbles precariously down hillsides to its port, a maze of helter-skelter streets and miradors connected by steep staircases and clanking funiculars.

At first glance, ‘Valpo’ (to use the local nickname) looks impenetrable and difficult to navigate. But, once you start wandering its switchback cobbled streets, the place somehow seems to make sense.

Its focal points are its cerros (hills, also meaning ‘quarters’ or ‘communities’ in this instance), some UNESCO World Heritage Sites. Cerro Alegre is a particularly rewarding place to lose yourself in, with its independent boutiques and handicraft shops.

Valparaíso is a city that bursts with unexpected quirks. While funiculars (called ascensors locally) carry you up to the highest hills, just outside the Ascensor Reina Victoria you can take a children’s playground slide back down.

Each of the cerros has far-reaching views over to the cranes and industry of the port, where cargo ships constantly spill out their goods onto the docks. Cruise liners visit the city more and more, and the docksides swell with crowds at certain times of day. Beyond all that lie beaches. Viña del Mar, a 20-minute drive away, is the locals’ choice.

Some of the best views are from Paseo Yugoslavo, one of the oldest parts of the city, whose streets are filled with rambling private residences and a former palace, Baburizza. It now houses the city’s fine arts museum.

Pablo Neruda’s one-time home, La Sebastiana, also boasts some of Valparaíso’s finest views. Designed to echo a ship’s hull, it’s crammed with his eccentric, sometimes nautical-themed memorabilia.

As a university city, Valparaíso has a certain carefree, playful ambience. Strolling its streets, you’ll rub shoulders with plenty of students, but also freewheeling bohemians and artists. They’re a far cry from the suited-and-booted commuters and well-heeled city workers of Santiago.

Valparaíso’s food and drink is especially celebrated in Chile. Many of the best restaurants and wine bars sit on stilts and often appear out of nowhere, tucked around a corner. They serve ceviche, seafood and inventive fine dining, with rich reds from the nearby Casablanca and Colchagua Valleys.

Street food is also big business in Valparaíso. It’s a place where you can grab a good empanada on the go as you explore.

Best time to visit Valparaíso

Spring to summer (October to April) brings the best weather. New Year’s Eve can be very busy and requires some forward planning if you’re looking to go to Valparaíso around this time.