Hostal Oregon

Valparaíso – known as Valpo to the locals – is a port city located around 120km west of the Chilean capital Santiago. One of its defining features is the numerous hillside houses, which were traditionally brightly painted so that fishermen could spot their homes as they returned from sea. Now, its streets are just as colourful, filled with world-class street art including murals by local legend INTI. Funicular railways run up and down the steepest hills, while the waterfront area is home to supermarkets, museums and nightclubs.

You can stay in edgy graffiti-decorated Valparaiso hostels, including one that has been painted by a collective of local artists. There's also a former brothel that dates back to 1897, as well as a Valparaiso hostel that has beds closed off with wooden doors to mimic shipping boxes – a nod to the city's port origins. Outdoors, you can find swimming pools for cooling off from the Valpo heat, and rooftop terraces for sundowners overlooking the vibrantly hued buildings.

The city of Valparaíso is a collection of 45 hills (cerros), with the most popular being Cerro Alegre and Cerro Concepción. Both have bohemian vibes with cobbled laneways, graffiti artworks and modern restaurants serving up Chilean favourites like ceviche. Down by the port, near Bellavista metro station, you’ll find several bars and cafés serving the local speciality of chorrillana – plates piled high with grilled meats, eggs, onions and fries.

The city has a good mix of history, art and architecture – and a couple of interesting museums. Nearby beach Caleta Portales is popular for its seafood restaurants and its laid-back vibe is ideal for an afternoon stroll. For a colourful taste of the city's culture, sign up for one of the many street art tours available. It's a fantastic way to check out the different neighbourhoods up close, while discovering how Valparaíso came to be one of the best places for street art in Chile.

Walking is the best way to explore the city's winding cobblestone streets and portside lanes. There are also 22 funiculars, which transport passengers up to the various hills. The metro system comprises a single line running 43km along the waterfront, linking Valparaíso to the nearby city of Viña del Mar. Terminal Rodoviario is a 15-minute walk from the centre. Here, buses connect to Santiago’s Pajaritos station as well as other cities in Chile like Antofagasta, and even across the border to Mendoza in Argentina.