1 EXPLORE Historic centre
Pedro de Valdivia founded Santiago in 1541 and the statue of the conquistador astride a horse in the Plaza de Armas is a good place to follow his footsteps. The Santiago Heritage Route traces the city's tumultuous history beginning at the plaza, with its imposing colonial-era cathedral. The walking trail passes historic buildings housing the Museum of Pre-Columbian Art and the former congressional building before arriving at La Moneda Palace, which still bears the scars of the 1973 coup that ushered in the reign of General Pinochet.
2 VISIT Pablo Neruda's House
Nobel Prize-winning poet and diplomat Pablo Neruda is one of Chile's most famous figures. A lifelong communist, he was variously feted and hunted by Chile's leaders. He was called the greatest poet of the 20th century by Colombian writer Gabriel Garcia Marquez. But his death in 1973 is rumoured to have been ordered by Pinochet. One of the museums dedicated to Neruda's life and literacy legacy is La Chascona, the house he built for his lover and later wife Matilde Urrutia, on the edge of Santiago's Parque Metropolitano. fundacionneruda.org/en
3 CLIMB San Cristobal Hill
Parque Metropolitano covers almost 722 hectares, and is criss-crossed with trails for joggers, cyclists and casual strollers. A zoo, swimming pools and gardens surround San Cristobal Hill inside the expansive park, while a statue of the Virgin Mary stands sentinel on top, her prim gaze taking in Santiago's splendid views. The peak rises 300 metres and is accessible by cable car or a brisk 45-minute walk.
4 EAT Like a local
From gourmet stars to market mayhem, Santiago's food scene is deliciously diverse. Chef Rodolfo Guzman's award-winning Borago draws on Chile's finest culinary traditions and unique geography – Patagonia, the Pacific coast and the deserts of Atacama – to craft exquisite dishes. Or pursue Anthony Bourdain's footsteps to La Fuente Alemana, the renowned sandwich shop, for a classic lomito (pork loin). Once fortified, plunge into the raucous La Vega Central, which houses 1200 stalls selling fresh fruit, vegetables, meat and other delicacies. Follow your stomach or join one of FoodyChile's tours for insider tips on the city's culinary life. foodychile.com
5 DRINK Pisco
Fractious neighbours Peru and Chile have fought over land, water and which country can rightly claim pisco as its own. Pablo Neruda called pisco "our sweet and treacherous national drink". Boisterous bar and restaurant Chipe Libre - Republica Independiente del Pisco avoids taking sides by offering a rich variety of the tipple from both countries. Pisco sour is the best-known cocktail using this local brandy, typically made with egg white, lime juice, sugar syrup and, in Peru, bitters. But endless variations range from piscola (pisco with beer) to sweeter concoctions such as the Serena Libre and Pisquina. chipelibre.cl
6 EXPLORE Barrio Lastarria
Santiago is a city of villages, each with a distinctive personality. Lastarria is a bustling neighbourhood of elegant early-20th-century architecture housing theatres, cafes and restaurants, design shops and galleries. The Museum of Fine Arts and Gabriela Mistral Cultural Centre offer a taste of Chile's cultural life. Stock up on handicrafts and antiques from one of the outdoor markets that take over the streets or relax in the nearby Parque Forestal.
7 DRINK Terremoto
Chile is one of the most earthquake-prone countries in the world, but it may be this concoction of pipeño (a fermented white wine), pisco, pineapple ice-cream and sugar that causes the ground to tremble. The terremoto was apparently created by a waiter in Santiago's infamous Taberna El Hoyo (The Hole) who sloshed ice-cream into a glass of pipeño for reporters covering an earthquake that struck the city in 1980s. Named after the Spanish word for earthquake, the first round is likely to leave the ground and your legs feeling wobbly. The next round is called replica or aftershock and will floor all but the sweetest tooth. elhoyo.cl
8 EXPLORE Pedal power
A city of 6 million people, hectic traffic and smog does not sound cycle friendly, but Santiago has surprisingly safe and diverse rides for the two-wheeled traveller. La Bicicleta Verde offers reasonably priced tours of the city's markets, landmarks and parks with a healthy dose of politics and culture. Further afield, there are tours of Valparaiso (plenty of steep hills) and surrounding grape-growing regions where there is likely to be more time off the saddle. labicicletaverde.com
9 VISIT Human Rights Museum
The 1973 overthrow of President Salvador Allende heralded one of the darkest periods in Chile's history. Thousands of people were killed and tortured by the police and military during General Pinochet's 17-year dictatorship. The Museum of Memory and Human Rights charts Pinochet's reign of terror, in at times harrowing detail, with displays of torture devices, photographs, testimony from survivors and letters written to family members from prisoners. museodelamemoria.cl
10 DANCE Cueca
A flurry of skirts, arch-backed men and handkerchiefs wielded with a flourish signals a performance of this dance. A regular fixture at El Huaso Enrique, a rustic restaurant in the Yungay neighbourhood, the cueca is said to mimic a strutting rooster as he seeks to seduce the demure hen. Versions of the dance are performed throughout South America, but it has national status in Chile where young and old take to the dance floor with relish and fancy footwork. elhuasoenrique.cl
11 VISIT Valparaiso
A change of pace from Santiago, Chile's second city is renowned for its vibrant nightlife and artistic vibe, and as the birthplace of Australia's third prime minister and the first Labor leader Chris Watson. A UNESCO world heritage site, Valparaiso's charm is not to be found in the uninspiring flat expanse around the port. Instead, get lost in the maze of narrow streets filled with galleries, bars and restaurants as well as row upon row of brightly painted 19th-century mansions improbably clinging to hills overlooking the sea. Rickety cable cars climb the steepest slopes for visitors too tired to walk.
12 EAT Hidden Kitchen
Carolina Blanco did not know what to do when she retired from her 30-year career at the Museum of Pre-Colombian Art. "I realised that every day was a Sunday and that was awful." The resourceful Blanco turned her penthouse into Puertas Adentro, a "hidden" kitchen dishing up a home-cooked meal and sparkling conversation to strangers from half a world away. One of several private restaurants in Santiago, Blanco plies guests with pisco and empanadas as soon as they enter her art-and-knick-knack-filled apartment, providing a unique culinary experience. protourschile.com; santiagopuertasadentro.cl (in Spanish only)
13 RIDE The foothills of the Andes
Cristian Waidele's sizeable, razor-sharp knife suggests danger lurks among the cacti and wildflowers of the Andean foothills on the edge of Santiago. But he mainly uses it as a bottle opener as he guides our horses along dirt trails towards a hilltop where a lavish barbecue and fine views of the city and snow-capped mountains awaits. Waidele is a convivial host as he regales our group with tales of horseriding adventures in Patagonia, which more intrepid travellers can saddle up and join. andesriders.com
14 RELAX Quinta Normal
A lazy afternoon can be easily spent in the Quinta Normal, an oasis of greenery that is also home to an array of cultural institutions including the national history museum (mnhn.cl), the city library (bibliotecasantiago.cl) and the Museo Artequin, an art museum aimed at children. Don't miss the food vendors selling a variety of Chilean fast food, from cooked meat sandwiches to cuchuflies, caramel-filled wafers.
15 EXPLORE Yungay
Named after a 19th-century military victory over arch-rival Peru, Yungay is one of Santiago's oldest neighbourhoods filled with graceful manor homes lining cobblestone streets. The Roto Chileno monument of a gun-toting soldier commemorates the 1839 military victory of the Chilean Army, although the Cerveceria Nacional, which boasts dozens of boutique beers, might be a more attractive destination. Boulevard Lavaud, meanwhile, houses the famed barber shop Peluqueria Francesa as well as a bar, restaurant and cafe.
16 FOLLOW Wine trail
Cabernet sauvignon, carmenere and sauvignon blanc are among the grape varieties nurtured in the wine regions surrounding Chile's capital. Bodegas Re (bodegasre.cl) is a small family affair in the Casablanca Valley that draws on ancient techniques of winemaking in clay amphoras, while the nearby Matetic Vineyards produces organic and biodynamic drops (matetic.com/en). Upscape runs wine tours that focus on boutique vineyards, with lodging in local haciendas, long lunches at wineries and winemaker-led tours. upscapetravel.com
17 STAY The Aubrey
Set in the restored 1927 mansion of Chilean railroad tycoon Domingo Duran, the walls of this boutique hotel have heard their share of political intrigue. Santiago's political elite, including a former president, held long lunches in the dining room of The Aubrey run by Australian Mark Cigana and partner William Martin. The atmosphere is calmer these days, with the hotel's 15 eclectically furnished suites, cobbled courtyard and swimming pool providing a relaxing retreat from the hipster restaurant and bar strip of nearby Bellavista. theaubrey.com
18 SEE Street art
There's barely a blank wall in Santiago thanks to the city's active graffiti scene. Politics and protest mix with spirits and fairy tales (and the odd scantily-clad woman) – all depicted with surprising skill and humour by the city's army of street artists. The bohemian Bellavista neighbourhood features beautiful street murals, some painted by professional artists and others by amateurs, which can be seen while bar hopping along its tree-lined streets. Santiago Street Art Tours runs cycling, vehicle and walking tours of the city's street art as well as painting classes with local street artists. stgostreetart.com
19 SKI The Andes
Snow-capped mountains provide a stunning backdrop to the Chilean capital as well as top-quality ski resorts little more than an hour's drive away. One of five resorts near Santiago, Valle Nevado receives an average of seven metres of snow each year across 60 kilometres of groomed slopes (half of them suitable for beginner and intermediate skiers). Lift queues are virtually non-existent, and long trails sparkle under bellbird skies dotted with condors. vallenevado.com/en
20 SURF The Pacific Ocean
The waves are large and the Humboldt Current ensures the water is bracingly cold along Chile's coast. The country's top surf spot is Pichilemu but the beach towns of Vina del Mar, Zapallar and Cachagua are easily reached from Santiago. Indeed, Chile's slender geography – more than 4300 kilometres long, but a mere 90 kilometres at its narrowest – means a skilled driver can ski and surf in the same day. The climate is Mediterranean, crowds are rare and the waves tend to be left-hand point breaks.
Andrew Taylor travelled with assistance from Qantas and AccorHotels.