Start in the heart of town, at bustling Plaza de Armas, dedicating the morning for tours of central museums like Museo Chileno de Arte Precolombino. Dive into a savory seafood lunch at Mercado Central, then hotfoot it up Cerro Santa Lucía to revel in the city from above. Break for afternoon tea and people-watching at a Barrio Lastarria cafe, then head to Bellavista for a long and lazy dinner before a night of carrete (partying) in the neighborhood's discos. Get inspiration on your second day at Pablo Neruda's house, La Chascona, then take in great views atop Cerro San Cristóbal. Head to Barrio Italia for shopping and brunch, then have a pisco sour at Chipe Libre before a show at Centro Gabriela Mistral – for contemporary works – or Municipal de Santiago (for classics).
On day three cruise out to the countryside with a visit to Cajón del Maipo or tour nearby wineries. In winter head for the snow at Tres Valles. Spend your fourth day admiring street art in working-class Barrio Brasil or contemporary art in the galleries of hoity-toity Vitacura, home to Chile's most acclaimed restaurant: Boragó. Toast your stay in Santiago with a wine flight at Lastarria's lauded Bocanáriz.