Exploring the Region
Many wineries, ski resorts, and coastal communities are close enough to Santiago to be explored on day trips, but your travel experience will be enriched if you opt to spend the night high in the Andes at a ski resort, or at a cozy B&B in the wine country. This way you'll spend less time in a vehicle and more time enveloping yourself in truly beautiful natural environments. A rental car provides a lot of freedom to explore at your own pace, especially if you are heading to the coast or visiting wineries. I've known more than a few travelers who, upon arrival or departure from Santiago, rent a vehicle at the airport, drive to the coast or the wine country, return the rental at the airport, and then taxi into Santiago (or vice versa). A good road map is essential. Once you exit the main highways, signposting is generally poor and Chileans will likely send you in the wrong direction than admit ignorance or an inability to help you.
Taking a bus is not a bad option either -- in fact, Santiago's national coach system is better than that of the U.S. Buses are modern and clean, and there are usually a dozen or so daily departures to most major destinations. Bus terminals are located downtown but can by reached by Metro. Taxis wait at regional bus terminals to deliver you to your hotel or wherever you need to go.
The Coastal Region
Beach retreats are the Chileans' favorite weekend getaway, and this section covers, in depth, Chile's better-known coastal cities, boisterous Viña del Mar and intriguing Valparaíso. Other smaller villages that dot the coast have their own strongly defined characteristics (and clear-cut socioeconomic levels), and visitors with a rental car will take pleasure in discovering each new village around the bend. You can also arrange a tour to coastal destinations that are not part of the "usual" itinerary.
Zapallar is home to Chile's moneyed elite, and it's the prettiest cove in the region. Cachagua and Maitencillo are where the upper-middle and middle classes own their second homes. Con Con is where you'll find the cheapest -- and the freshest -- seafood restaurants, and a Radisson resort; Reñaca is where the young and gregarious socialize and loll in the sun. Farther south is another middle-class hub, Algarrobo (nothing much to see here), and down-at-the-heels Cartegena, the oldest seaside resort in Chile, which has now fallen out of favor (to give you an idea, Chileans commonly use the phrase "tackier than a honeymoon in Cartegena"). A popular destination on the tourist map these days is Isla Negra, because Pablo Neruda spent most of his time in his house here, which is now a museum, and you can visit the up-and-coming San Antonio wine region on the way. The port city of San Antonio, south of Isla Negra, is a grim, desolate place that is often unavoidable for travelers who pass through due to restricted coastal access north of Isla Negra.
Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.