1. Bohemian vibes in Valparaíso
Few disagree that Valparaíso is the city that most oozes effortless, bohemian cool. A now infamous backpacker stop off, Valpo is a labyrinth of winding, graffitied streets, brightly painted buildings and rickety nineteenth-century ascensores shuttling you into the city’s distinctive skyline of hills.
It’s in these cerros that Valpo’s real magic, and the chance to appreciate the creative, liberal leanings of its residents, are found. Cerro Bellavista’s sprawling walls of street art culminate in the Museo de Cielo Abierto (the Open Sky Museum): a poignant collection of murals defiantly proclaiming artistic freedom. Started in 1973, they were only completed in the early 1990s after the fall of the Pinochet dictatorship.
Valpo’s excellent nightlife also secures this city as the trendiest spot on the Chilean backpacking trail. Dancing until dawn is guaranteed in the student-favourite super club El Huevo, while the seafront La Piedra Feliz bundles every type of live music into four rooms. For a more relaxed evening, Casa Cervecera Altamira offers refreshing craft cerveza and mellow jazz in a cosy setting.
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2. Dancing in delicious Santiago
An oft-ignored Latin American capital, Santiago has a surprisingly varied live music scene and excellent restaurants. Santiaguinos certainly see themselves as more on trend than the rest of the country, and this modern city is quick to prove its cool credentials.
While foreign crowds are normally drawn to bars such as Latin-inspired Maestra Vida in central Barrio Bellavista, heading a little further from the city centre is where you’ll find a refreshing display of Chileans’ eclectic musical tastes.
Discover the latest local bands at popular rock club Batuta in Plaza Ñuñoa, or stumble upon the truly underrated of Santiago music: Club de Jazz. Once located in nearby Ñuñoa, where legends such as Louis Armstrong and Elvin Jones topped the bill, nowadays you’ll find the Club de Jazz set in the glorious old colonial building of La Fabbrica restaurant in La Reina.
Santiaguinos also know a thing or two about fine-dining. Follow the crowds to the up-and-coming restaurants in trendy Lastarria neighbourhood; pair pisco with dishes from Chipe Libre, or sample the country’s extensive wine tradition without even leaving your chair by putting yourself into the expert hands of Boca Nariz.
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3. Coastal cool in Iquique
While the northern stretch of Chilean coastline is typically neglected by visitors, Iquique is an oasis of cool in the undulating sand dunes of the region. It’s an under-appreciated haven for sun worshippers, as well as those seeking to capitalize on the region’s wealth of extreme sports.
A recent addition to the global surfing circuit, Iquique is fast becoming a pro-surfer’s playground thanks to its epic, world-class waves. A short distance from the city, the 18ft swells of La Bestia and El Colegio bays keep wave junkies occupied.
For those with a less adventurous head, Playa Cavancha in downtown Iquique is a relaxed beach perfect for soaking up rays or sipping the nation’s favourite cocktail – the pisco sour.
Adventure fanatics can get their fill by heading to the top of the looming Cerro Dragon sand dune that overlooks the city. Sandboarding tours skim down steep, golden hills, while paragliding allows you to soar though the Iquique skies and out towards the Pacific.
4. Partying in Pucón
Further south, Pucón blends lazy afternoons and high-adrenaline activities, making it a small but perfectly formed hangout. Each summer, thousands of backpackers and Chileans alike flock here for back-to-back parties in the bars along the main thoroughfare, Avenida O’Higgins, while the black lava beaches of the town’s lake, La Poza become an excellent spot for sweating out the previous night’s excesses.
But it is the instantly visible bulk of Volcán Villarica that has established Pucón as one of Chile’s most unmissable cities. Climb this active volcano during the summer months (spurting lava included if you’re lucky) or don your coolest ski gear and hit its slopes when fresh snowfall crowns its peak.