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No matter where you fly from, you'll likely arrive in Chile's capital early in the morning after an all-night flight. Unless you're one of those rare people who can sleep the entire night on a plane and arrive refreshed at your destination, reward yourself with a couple of hours' shut-eye at your hotel before setting out to explore the city.
The neighborhoods, small and large, that make up Santiago warrant at least a day and a half of exploration. A trip up one of the city's hills—like Cerro San Cristóbal in Parque Metropolitano or Cerro Santa Lucía—lets you survey the capital and its grid of streets. Any tour of a city begins with its historic center; the cathedral and commercial office towers on the Plaza de Armas reflect Santiago's old and new architecture, while the nearby bohemian quarter of Bellavista, with its bustling markets and colorful shops, was built for walking. But Santiago's zippy, efficient metro can also whisk you to most places in the city, and lets you cover ground more quickly. Avoid taking the metro during the morning and evening rush hour.
Alas, if you're here in the winter, gloomy smog can hang over the city for days at a time. Your first instinct may be to flee, and one of the nearby wineries in the Valle de Maipo will welcome you heartily. If it's winter and you brought your skis, Valle Nevado, Chile's largest downhill resort area, lies a scant 16 km (10 mi) outside Santiago.
A 90-minute drive west from Santiago takes you to the Central Coast and confronts you with one of Chilean tourism's classic choices: Valparaíso or Viña del Mar! If you fancy yourself one of the glitterati, you'll go for Viña and its chic cafés and restaurants and miles of beach. But "Valpo" offers you the charm and allure of a port city, rolling hills, and cobblestone streets with better views of the sea. Nothing says you can't do both; only 10 km (6 mi) separate the two, and a new metro system connects them. Overnight in either city.
You certainly could drive the nearly 1,500 km (900 mi) to Chile's vast El Norte Grande, but a flight from Santiago to Calama, then a quick overland drive to San Pedro de Atacama will take you no more than 3½ hours. That a town with such a polished tourism infrastructure could lie at the heart of one the world's loneliest regions comes as a great surprise. This is one of the most-visited towns in Chile, and for good reason: it sits right in the middle of the Atacama Desert, with sights all around. You'll need at least two days here to do justice to the alpine lakes, ancient fortresses, Chile's largest salt flat, and the surreal landscape of the Valle de la Luna.
San Pedro to Iquique is a drivable 500-km (300-mi) journey, but a flight up from Calama saves you more hours of precious vacation time. There's not much of interest in Iquique itself, other than some nice white-sand beaches and the nearby ghost town of Humberstone, but the town makes a good base for visiting the hundreds of geoglyphs at the Cerros Pintados—it's the world's largest collection—in the Reserva Nacional Pampa del Tamarugal. The largest geoglyph on Earth, the Gigante de Atacama, is nearby.
If you've come this far, head to Chile's northernmost city, with a temperate climate and a couple of creations by French architect Gustave Eiffel. The main attraction, however, is the nearby Museo Arqueológico de San Miguel de Azapa and its famed Chinchorro mummies, which date from 6,000 BC. Their Egyptian cousins are mere youngsters by comparison.
A morning flight on your last day gets you to Santiago in plenty of time to connect with an overnight flight back to North America or Europe.
Although it's quite easy, and even preferable, to explore Santiago, Viña del Mar, and Valparaíso using public transportation, a car makes it easier to visit the sights and towns in El Norte Grande. That said, it is possible to get around using buses, which connect most of the cities of El Norte Grande. Once in San Pedro de Atacama or Iquique, you can hook up with various tour agencies to visit sights not accessible by bus. There are frequent flights from Santiago to Calama and from Arica back to Santiago.