Santiago is Chile’s transportation hub, and four days are enough to explore the capital and nearby wineries and seaside towns within an hour’s drive. This short trip avoids long flights and has a leisurely pace, making it a good addition to a longer journey or a stopover arrangement.
Weapons Square and the Cathedral → Santa Lucía Hill → La Moneda Palace and the historic district → In the evening, hike up Cerro San Cristóbal to overlook the city and see the silhouette of the Andes at sunset.
Head to the Maipo Valley or Casablanca Valley to visit wineries and taste Carménère and Sauvignon Blanc, enjoy a vineyard lunch, and return to the city in the evening. Most wineries require advance reservations, and some offer half-day tours with pickup and drop-off.
Explore the graffiti-filled streets and take the funiculars in the colorful hillside city of Valparaíso → Visit the former home of poet Pablo Neruda → Stroll along the seaside in Viña del Mar, then return to Santiago in the evening. The hilly city has many slopes, so wear comfortable shoes.
In winter, you can visit ski resorts in the Andes; in other seasons, go hiking in the valley or head to Cajón del Maipo → In the afternoon, visit a market to sample seafood and pisco → Fly out or continue south in the evening. If time allows, use this day to explore Santiago’s museums and neighborhood cafés to experience daily city life.