Gálvez Passage in Valparaíso, Chile
Mark Orwoll

How to See Chile When You Have Less Than a Week

How much does the average person know about Chile? Culinary enthusiasts will smack their lips while describing Chilean sea bass and Colchagua Valley wines. History buffs may describe Valparaíso as one of the 19th century’s great seafaring ports. English majors can quickly name poets Pablo Neruda and Gabriela Mistral, both Nobel laureates. But although the country is gaining ground as an esteemed travel destination, many folks outside of South America don’t have much to say about Chile after “long and skinny.” 

Obviously there’s much more to this complex and beautiful country, as travelers can learn during a visit of even just four or five days. True, that’s not enough time to enjoy the Atacama Desert in the far north or the Torres del Paine mountains in the far south, but an itinerary focusing on three cities—Viña del Mar, Valparaíso, and Santiago, the capital—makes for a superb introduction to the Land of Poets.

Pictured: Gálvez Passage in Valparaíso

Chile's Casablanca Valley
lopezlago / Flickr
Day One: The Lay of the Land

The 90-minute drive from Santiago Airport to Viña del Mar on the Pacific coast is a visual feast. An early-morning dove-gray mist often rises above the roadside vineyards. Elsewhere, hills—some soft and rounded, others rocky and vertical—seem scattered at random across a vast agricultural plain. Besides the grape vines, most of the greenery is limited to scrub and stunted pines. A tight cluster of hills unexpectedly opens onto sprawling grape plantations running to another set of hills on the horizon. And then you begin to smell the sea. 

Flower clock in Viña del Mar, Chile
Mark Orwoll
A Stroll Around Viña del Mar

Since 1945, the top place to stay in Viña del Mar (just Viña to locals) has been the Sheraton Miramar Hotel, built on a rocky headland on the main coastal road. Every room faces the ocean, with sidelong views of Viña or its historic neighbor to the south, Valparaíso. After you settle into your room, take a walk outside. Flower baskets dangle from nearly every streetlamp, and an enormous botanical clock built in 1962 for the World Cup helps justify the town’s nickname: the Garden City. Other sights worthy of a stroll: the seaside 1908 Wulff Castle (which has a small history museum), the city’s venerable casino, the nightclub- and restaurant-filled Poniente neighborhood, the Fonck natural history museum, and Quinta Vergara park, where you can see plants from across the Americas and Asia. End the afternoon with an icy Cristal cerveza at one of the lively outdoor student cafés lining the western end of Calle Valparaíso or a pisco sour at an upscale bar in Poniente.

Divino Pecado restaurant in Viña del Mar, Chile
Mark Orwoll
Dinnertime: Divino Pecado

You only have to look at a map to grasp Chile’s close connection to the coast. Swimming in Viña, though, may prove problematic because of rough surf and frequent shark sightings. (Also, the water is “so cold it hurts,” according to one local.) But that doesn’t mean you can’t appreciate the bounty of the ocean. One of the best places to satisfy seafood cravings is Divino Pecado, an intimate spot within sight of the photogenic casino in Poniente. Set in a 90-year-old building with paneled walls, parquet floors, and a tiled, glassed-in patio, Divino Pecado is a Viña mainstay. It’s probably best known for salmon that’s smoked in-house daily and served with leeks, cream, and a taste of sparkling wine. But you also can’t go wrong with the kitchen’s baked scallops with camembert, farmer’s cheese, and crema fresca; a piquant and super-fresh ceviche; mussels in gruyere and chardonnay, with just a hint of ginger; and, for the non-fish eater, osso buco under a sauce of black mushrooms and cabernet sauvignon.

Valparaíso, Chile
Loïc Mermilliod on Unsplash
Day Two: Valparaíso—Jewel of the Pacific

Located just down the coast from Viña, the cultural capital of Chile is a brash, vibrant, gritty settlement spread across 42 hills (44, according to some sources) next to a vast natural harbor that made the town one of the most famous ports in South America in the 1800s. The completion of the Panama Canal in 1914 curbed the city’s fortunes, and crime has risen in recent decades—though tourist areas are relatively safe. The city’s brightly painted houses and ornate historic structures give the place a zestful appeal, and the locals, called Porteños, are welcoming. In 2003, UNESCO named Valpo a World Heritage Site for its idiosyncratic architecture and organic urban design. Caution: It’s better to take an Uber than to attempt driving on the narrow, nearly vertical hillside streets, no matter how picturesque they may be.

Museo La Sebastiana in Valparaíso, Chile
Marcelo Ois Lagarde [CC BY-SA 3.0], via Wikimedia Commons
Museo La Sebastiana

Pablo Neruda (1904–1973) is considered the poet of the Chilean soul. Full of contradictions, he was a politician and diplomat who lived a bohemian lifestyle, a committed Communist who broke with Mao over the Cultural Revolution, and the “people’s poet” who was rich enough to own three grand homes. One of them, La Sebastiana, is now a must-see museum. In addition to having one of the best views of the city, Neruda’s multilevel home on Cerro Florida (cerro means hill in Spanish) holds intriguing artifacts from the poet’s life—a wooden carousel horse purchased in Paris, an open fireplace he designed himself, the bar where he entertained friends while wearing a silly fake mustache, and the window-lined living room where he and his guests held bang-up New Year’s Eve parties while fireworks exploded over the city.

Reina Victoria ascensor in Valparaíso, Chile
Rodrigo Fernández [CC BY-SA 4.0], via Wikimedia Commons
Ascensor to Cerro Alegre

There are so many steep hills in Valparaíso that in the early 1900s the city created a system of outdoor elevators, called ascensores, to move people quickly and cheaply between downtown and the uphill neighborhoods. The 1903 Reina Victoria ascensor (pictured) rises from Cummings Street at a 52% grade to reach Cerro Alegre (“happy hill”), so named for its colorful houses and charming lanes. Almirante Montt and the surrounding streets are crammed with bars, youth hostels, restaurants, ice cream shops, boutiques, galleries, street vendors, and a steady stream of people heading to and from the funicular. The area is full of families during weekends when the weather is nice.

Tres Peces restaurant in Valparaíso, Chile
Mark Orwoll
Lunch Break: Tres Peces

Tres Peces, a strictly seafood restaurant on Cerro Concepción (adjacent to Cerro Alegre) is dedicated to sustainable fishing and buying directly from local fishermen the same day the food is served. (As in many coastal nations, overfishing and out-of-season fish are ecological problems in Chile.) On the menu: conger eel soup, rockfish with potatoes, garlic shrimp, and a bouillabaisse-like stew—everything simple and straightforward. “We focus on what we can get fresh from the sea,” says co-owner Meyling Tang, an ardent advocate of responsible fishing. “We’re making the effort to buy only what’s legal, and only seasonal fish. So the menu changes every day as a result.” The old-world-style bistro is one of the trendiest spots in town. Reservations aren’t accepted, so don’t be surprised to find lines down the street.

Guide Juan Astorga leads a street art tour in Valparaíso, Chile.
Mark Orwoll
Street Art Tour

Back on Cerro Alegre, visitors can wander the cobbled lanes to take in the thriving street-art scene. A local guide is a good idea—someone like Juan Astorga (pictured), a graphic designer and photographer who counts many of the street artists as friends. Gálvez Passage is super-narrow, with a deep gutter on one side and walls decorated with cartoonlike murals. At a bend in the street is a pair of red doors decorated with flowers—“the most photographed doorway in Valparaíso,” according to Astorga. Calle Tempelman—“the heart of Cerro Alegre,” says Astorga—features murals by artists whose works also appear in local galleries. Street art is taken seriously here. “The graffiti artists live by a code,” Astorga says. “The rule is you don’t touch a mural. And the people of Valparaíso like the murals because they take over from the ugly, illegal graffiti.”

For more information on Juan Astorga's tours, email valpostreetart@gmail.com.

Santiago, Chile
Image by Horst Engelmann from Pixabay
Day Three: Santiago—the Big Picture

As you drive back to Santiago, the glacier-capped Andes on the city’s eastern border are especially prominent. And so, unfortunately, is the smog. This city of 6.5 million inhabitants does battle daily with pollution—a brown haze gets trapped between the mountains and the sea (60 miles to the west). Still, Santiago has all the attributes you’d expect from a capital city: theaters, concert halls, museums, universities, and varied neighborhoods. A recommended hotel is the Santiago Marriott, not just because it has a gorgeous lobby and large rooms (even the smallest is more than 450 square feet), but also because it has what many consider one of the premier restaurants in the city, the Latin Grill. The hotel is a good choice for families, too, owing to its proximity to parks, a large supermarket, and a shopping mall.

Emporio La Rosa cafe in Santiago, Chile
Mark Orwoll
Lunch Break: Emporio La Rosa

Emporio La Rosa started in 2001 as a simple café, then began offering ice cream made in-house. The place quickly developed a huge following and today has numerous locations throughout the city. La Rosa’s key selling point is that the ice cream uses only Chilean ingredients. But don’t neglect the lunch menu. Try an empanada stuffed with chopped beef, olives, onion, hard-boiled egg, and raisins;  or a hearty stew with corn, tomato, minced onions, and finely sliced beef with slow-cooked natural tomato sauce. Afterwards, go bonkers with ice cream choices such as honey (from Patagonia), lemon, rose banana, and papaya.

Plaza de Armas in Santiago, Chile
Mark Orwoll
Walking Tour of Historic Neighborhoods

“When you walk around Santiago,” says local guide Connie Llanos, “remember that the Andes are to the east. In fact, when we people from Santiago go to other cities, we always get lost because we can’t see the Andes.” Start your walk in Lastarria, a neighborhood filled with tree-lined streets, cool old buildings, inexpensive restaurants, and lots of college students and other young people. “We haven't kept a lot of our old buildings because of all the earthquakes we’ve had,” says Daniela Perez, a Santiago-based publicist, “but you will find older architecture in Lastarria.” 

Not far away, Santa Lucía Hill is where the city was founded in 1541. Today, the hilltop Hidalgo Castle (1817) is used for private events like wedding receptions. Savor an excellent view of Santiago on the Terraza Caupolican just below the castle summit. The nearby Plaza de Armas (pictured), the city’s palm-shaded main square, is the beating heart of downtown. Pedestrian promenades in this area lead to boutiques, coffee houses, snack shops, and museums. 

For more info on Connie Llanos's tours, email her at cconstanza.llanos@gmail.com. 

The Latin Grill in Santiago, Chile
Mark Orwoll
Dinnertime: The Latin Grill

The Santiago Marriott’s Latin Grill is a paean to Chilean culinary excellence. The banquette-lined walls, soothing brown color scheme, and subtle lighting lend a sense of intimacy to what is actually a big-hotel restaurant. But it’s the food you’ll be raving about: crispy baked goat cheese with duck confit; lamb ribs and pumpkin tortellini with onion cream and toasted hazelnuts; mountain salmon alongside abalone; smoked octopus in black olive cream; corvina and king crab on a bed of green bean purée—are you hungry yet? Chef Luis Cruzat has made it part of his mission to use only ingredients from Chile. Dinner here is a bit of a splurge, but worth it.

Viñamar in Chile
Mark Orwoll
Day Four: Viñamar Winery Tour

Though some foreigners think of Chile’s vintages as upstarts, the wine industry here predates California’s. A winery tour is an absolute must (ask your hotel for recommendations). A typical itinerary might begin with a drive through Curacaví and into the fertile Casablanca Valley, about an hour from Santiago, where 14 wineries make up the Ruta del Vino. One of the more interesting is Viñamar, with its estate building, tasting room, patios, and restaurant. The valley lies in the path of cool winds coming off the ocean 20 miles to the west—conditions especially conducive to making white wines like chardonnay and sauvignon blanc. In nice weather, tastings are held on a handsome terrace overlooking acre upon acre of vineyards. Be sure to try the sparkling wines; they’re not produced anywhere else in the valley.

Macerado restaurant in Chile
Mark Orwoll
Lunch Break: Macerado

Visitors to Viñamar—or any other Casablanca Valley winery—would do well to time a visit so they can have lunch at Macerado on Viñamar’s second-floor terrace. Start with a glass of sauvignon blanc and an appetizer of charred octopus from Chile’s remote Juan Fernández Islands. For a main, choose the roast beef in a syrah demi-glace with creamy polenta and tomato confit. End things on a sweet note with the poached pear and a glass of sparkling pinot noir extra brut. Then just sit there for a few minutes, taking in the glories of the Chilean countryside and the faraway mountains on the horizon.

Aerial tramway in Santiago, Chile
Sfs90 [CC BY-SA 4.0], via Wikimedia Commons
Day Five: Santiago's Best View

The aerial tramway in Parque Metropolitano, just 3 miles northeast of Plaza de Armas, rises to the top of Cerro San Cristóbal. An overlook offers views of downtown and the surrounding mountains. (A thin layer of sawdust-brown smog shouldn’t mar the panorama entirely.) There are several snack bars and cafés at the summit selling ice cream, coffee, hot dogs, and other light refreshments. You can also visit the stone church at the hill’s highest point and shop for souvenirs at a handful of stalls. Return to street level via the historic open-air funicular, accessed via a churchlike station at the top and a castle-like station at the bottom. Best of all, the funicular drops guests off in Bellavista, one of the most intriguing neighborhoods in all Santiago.

Castillo Rojo in Santiago, Chile
Mark Orwoll
Bohemian Bellavista

Bellavista began as a worker’s neighborhood in the 1920s, with tree-shaded streets and modest homes. In the ensuing years, the residents began painting their houses in bright colors. When poet Pablo Neruda moved here in the 1950s, the bohemian crowd soon followed, and Bellavista’s fortunes were set. Don’t expect beatnik poets and starving artists in paint-stained smocks today, though, because Bellavista is far too popular—and expensive. But it is still a scenic and fun neighborhood for strolling. “And there’s street art everywhere,” as local guide Connie Llanos points out. The central avenue, Constitución, strings together restaurants, bars, and small shops. At one end of the main drag is Castillo Rojo (pictured), a highly Instagrammable rust-colored chalet now run as a hotel.

Patio Bellavista in Santiago, Chile
Mark Orwoll
Lunch Break: Patio Bellavista

The Patio Bellavista complex on Constitución is tons of fun, a visual and culinary smorgasbord, and a hugely popular gathering spot for locals. Essentially, it’s an outdoor shopping mall, but there are way more restaurants than you’d expect at a typical food court. Choose from Italian at Vendetta, sushi at Panko, cocktails at Cosmopolitan, steaks at Montana, pizza and beer at the Pizza Factory, Tex-Mex at Rosita, seafood at Puerto Bellavista, Colombian dishes at La Casa en el Aire, Peruvian dishes at Tambo, and burgers at Mr. Jack. Other storefronts sell souvenirs, jewelry, clothing, and accessories in a festive al fresco setting. If Patio Bellavista is too busy, try Galindo, one block north, for authentic Chilean cuisine and laid-back vibes. 

Museo La Chascona in Santiago, Chile
Mark Orwoll
Museo La Chascona

Pablo Neruda felt an affinity with Bellavista. In 1953, the poet began building a house here that would eventually develop into a small compound called La Chascona. The place was intended for Neruda’s mistress, Matilde Urrutia, who would become his third wife (and whose unruly red hair gave the house its Spanish name). The most memorable stops on the audio tour are the comfortable library at the compound’s highest point; the open-air “summer bar” (as opposed to the maritime Captain’s Bar in another building); a secret passage that allowed Neruda to hide from unwanted guests; and the “lighthouse”-style living room, where Neruda lay in state after his death in 1973. Today, the house is as cheery as when Pablo and Matilde lived here. A visitor might half-expect Neruda himself to pop out of a secret passageway and suggest a pisco sour in the summer bar.