Over the past 14 years, I’ve traveled to Chile roughly 20 times for work and pleasure. I’ve braved the Atacama, the driest desert on earth, and touched the glaciers of Patagonia. 

I’ve ridden horses alongside the Pacific coastline and hiked the Andean foothills. I’ve also explored Santiago, Chile’s capital, noting its best restaurants, bars, hotels, wine shops and cultural points of interest.

As Wine Enthusiast’s contributing editor for South America, I’ve also spent time in Chile’s wine valleys, from Elqui and Limarí in the north to the central regions of Maipo, Casablanca, San Antonio, Cachapoal, Colchagua, Curicó and Maule. 

Chile is one of my favorite wine-producing countries to visit. It’s a mostly safe nation that has worked hard over the past two decades to escape the shadows of its darkest times (from 1973–1990, the military ran the country). Thanks to its populace’s strong work ethic, the country’s roads and highways, telecommunications systems and politics all have taken huge turns for the better. 

Today, Chile is arguably South America’s most stable, accessible country. Home to talented chefs, otherworldly seafood, genuinely nice hotels and hundreds of wineries, big and small, it’s the perfect place to spend a week, especially if drinking good wine and eating well are priorities. 

Spend an awesome week in Chile, starting with two days in Santiago, followed by two days in the Casablanca Valley wine region and the coastal city of Valparaiso. Then enjoy two more in the Colchagua Valley, one of Wine Enthusiast’s Top 10 Wine Travel Destinations of 2012. 

Use this insider’s guide as your road map, and you won’t be disappointed.

Santiago 

Day 1

Check into the Lastarria Hotel, a boutique property housed in a renovated 1920s mansion. It’s situated in the heart of Lastarria, a historic neighborhood that has undergone a massive renaissance over the past several years. This charming hotel is walking distance from a collection of trendy restaurants, bars, boutiques, museums and one of the city’s must-see landmarks, Santa Lucía Hill, where Santiago took root in the 16th century. 

Prior to summiting Santa Lucía, where a panoramic view of the city is your reward for scaling countless steps, fuel up at Fuente Alemana (58 Ave. Libertador Bernardo O’Higgins; no Web site), one of the capital’s most popular sandwich shops. Here, the lomito (roast pork) and churrasco (steak), piled high with toppings like smashed avocado and mild green chilies, have been filling stomachs for decades. 

Dinner on your first night should be at Bocanáriz, a year-old wine bar and small-plate joint just a short stroll from the hotel. Sip themed flights of Chilean wines, select from among 35 by-the-glass selections or drink one of the 300 bottles listed on the hulking wall-mounted chalkboard. Owners Daniela Lorenzo and Katherine Hidalgo are winemakers committed to showcasing only Chilean offerings from nearly every bodega in the country. 

Finish the night with an artisan pisco, Chile’s national spirit, at The Aubrey, a fashionable hotel in the Bellavista neighborhood that has a lovely courtyard and bar.

Day 2 

Start the day in Santiago by touring the home of the late Pablo Neruda, Chile’s Nobel Prize-winning poet and statesman. Called La Chascona, or “the tree house,” this multistory home in Bellavista is filled with artwork and knick-knacks that provide insight into how Neruda, a bon vivant and wine lover, lived during the 1950s. 

Ready for lunch? Head to the Providencia neighborhood and the original Bar Liguria, a longtime favorite known for its party vibe, wacky wall hangings, funky illustrated menus and authentic Chilean grub. Start with a Pisco Sour, the national cocktail, before moving on to a bowl of viscous crab soup (chupe de jaiba), hake cheeks topped in a garlic sauce called pil-pil, and finally, some grilled lamb chops (chuletillas de cordero). 

Satiated and lubricated, it’s time to visit Santiago’s one true urban winery, Viña Santa Carolina. Devastated by a major earthquake in 2010, it has been restored to a level of grandeur that surpasses what previously existed. Taste the signature Herencia Carmenère inside Santa Carolina’s original bodega, which has been declared a national monument. In addition, this 135-year-old winery, which can be reached by metro or car, boasts beautiful colonial-style gardens. 

For dinner, consider Baco Vino y Bistro (113 Nueva de Lyon; no Web site) in Providencia. This winemaker haunt serves Gallic classics like briny oysters and a duck confit that might make you think you’re in Bordeaux. 

If you prefer, you could hit Mestizo, located in tony Vitacura. This swanky spot features indoor-outdoor seating and a hopping bar with views of Bicentennial Park. The open kitchen turns out wine-friendly dishes like grilled skirt steak (entraña) and pan-roasted conger eel (congrio). 

Strolling Santiago

The Singular (thesingular.com) runs a spectacular hotel in Patagonia and is expected to open its first Santiago location in 2014. Clotheshorses should explore the Museo de la Moda, which is run by the Yarur textile family and features superbly curated exhibits related to international fashion. No trip to Santiago is complete without passing through the Gustave Eiffel-designed Mercado Central, especially if you enjoy seeing all types of fresh seafood and produce on display. Seeking Chilean wine to take home? La Vinoteca and El Mundo del Vino are Santiago’s best wine shops and can pack a plane-ready case of your favorite vinos. Other commendable restaurants include Miraolas and Aqui Está Coco, which both specialize in top-notch seafood; Tiramisu for good pizza and oversized salads in buzzing surroundings. For delicious empanadas, try Don Benito. It’s located 45 minutes outside of the city in Isla de Maipo, where there are a number of wineries worth visiting, including De Martino, Odfjell, Santa Ema and others.

Casablanca Valley and Valparaiso 

Day 3 

Having experienced the hustle and bustle of the city, now it’s time to breathe in the smell of Sauvignon Blanc and the Pacific Ocean. About 45 minutes west of Santiago, the Casablanca Valley is Chile’s preeminent cool-climate wine region. 

Another 30 minutes westward from Casa-blanca and you’re in Valparaiso, historically Chile’s main port city. It’s now a magnet for artists, international travelers and anyone with a Bohemian leaning.

But before arriving in Valpo (as the locals call it), your first stop should be at Viña Emiliana, an organic and biodynamic producer of top-quality Sauvignon Blanc as well as Pinot Noir and Chardonnay. Take one of the morning tours, taste a few of Emiliana’s wines, then move a bit further west to Casas del Bosque, one of Chile’s best makers of crisp, pungent Sauvignon Blanc. Here, you can tour the vineyards and winery, but the highlight is lunch at Tanino, the winery’s on-premise restaurant. The eatery features dishes like seared Pacific salmon with crunchy shrimp and white asparagus paired with Chardonnay, or phyllo pockets stuffed with wagyu beef and goat cheese that go ideally with the winery’s Syrah.

After lunch, continue on to Valparaiso and check into Casa Higueras or the nearby Zero Hotel. Both have cool vibes and offer excellent views of the harbor. Dinner is within walking distance of both hotels, either at Café Turri, where traditional seafood and a superb wine list await, or Pasta e Vino (352 Templeman; no Web site), for what many consider the best Italian food in Chile. A nightcap at Café Vinilo is a good way to finish your day.

Day 4 

After three fairly hectic days, today is for relaxing. But not before getting lost amid the labyrinth of narrow streets that snake up and down Valparaiso’s hillsides. After your morning walk, head north in the direction of Viña del Mar, Chile’s one-town Riviera, where you can catch some rays on the beach before having a seafood lunch and a nice bottle of wine at Portofino. 

After lunch, head back toward Santiago, but detour to the San Antonio Valley. Check into La Casona at Matetic Vineyards, one of Chile’s finest winery-based hotels. A stay here includes all meals and a tour of Matetic’s ultramodern winery, which puts out superb Syrah and Sauvignon Blanc as well as interesting Gewürztraminer and Riesling. Get a good night’s rest in your fluffy bed, because tomorrow you’re going to cover some ground.

Colchagua Valley 

Day 5 

The ride from San Antonio to the Colchagua Valley will take at least three hours. But when you arrive in this warm-climate wine region located about 100 miles south of Santiago, you’ll be happy you came. It feels a lot like Napa Valley here—except that in Colchagua, many locals still get around on horseback and wear ponchos and chupayas (wide-brimmed cowboy hats).

Check into the Residence at Lapostolle, a five-star Relais & Chateaux property perched above the famed Apalta Vineyard that Lapostolle shares with other wineries, including Montes, Ventisquero, Santa Rita and Neyen. The Residence is Chile’s most high-end, high-priced winery lodging option. The four cabins that comprise the hotel, however, come with every luxury, from high-thread-count sheets and spacious walk-in closets to wood-burning fireplaces. Included in the tariff are three meals each day, plenty of wine, a tour of Lapostolle’s architecturally impressive Clos Apalta winery, horseback riding through the vineyards and transportation throughout the valley. For more affordable options, contact the offices of Ruta del Vino, which handles wine-related tourism in the valley.

For restaurant meals, try these: Rayuela, located at Viu Manent winery, which specializes in grilled meats and fish; La Casita de Barreales, offering Peruvian-inspired cuisine in a quaint adobe house; and Vino Bello, where Italian dishes are prepared by a Chilean chef who trained in California.

Day 6 

Your final full day starts in Santa Cruz, Colchagua’s main town, with a visit to the Museo Colchagua. Exhibits here detail Chilean history, from precolonial days through colonialism and modern times. You will see more amber, nautical maps, weapons, tools and machinery than you’d ever imagine existed, and it’s easy to spend hours here, if not the whole day.

If you’re traveling with a group of six or more, you should reserve a daytime “session” with Pilar Rodríguez, a personable and skilled private chef who runs her Food & Wine Studio at Viu Manent. For a memorable lunch, take part in Rodríguez’s three-hour interactive session. Diners work with the chef to prepare a six-course wine-and-food lunch that incorporates such native Chilean ingredients as merkén (a spice), quinoa and maracuyá (passion fruit). And, while on the subject of doing it yourself (or at least with a teacher), consider blending your own wine while touring Viña MontGras.

For your final night’s stay, head back toward Santiago and get off the Pan-American Highway just north of San Fernando. Check into Hotel Casa Silva, one of Chile’s first boutique winery hotels, and enjoy dinner overlooking the property’s polo field. On the walls of the restaurant, which also functions as the polo clubhouse, are hundreds of photos of the Silva family and others participating in polo matches and other equine events. It’s a perfect final taste of the huaso (cowboy) culture that, along with wine, defines life in the Colchagua Valley. 

The Great Beyond

Should you be spending more than a week in Chile, there are a number of places worth visiting that require a flight from Santiago. Among the best are San Pedro de Atacama, a quirky but civilized gateway to the world’s most arid desert; Torres del Paine National Park in Patagonia; Easter Island, where the eco-resort Explora has its newest outpost; and the southern Lake District, near the city of Puerto Montt, where one can fish for wild trout and salmon, or head inland to see volcanoes like Pucón and Villarrica.

WE's Editor for South America set out on a journey to discover what Chile has to offer. From Santiago to Colchagua Valley, he explored nine wineries and sat down with winemakers at each to talk terroir, top wine picks and tourism opportunities. Watch exclusive Chile Expedition video >>>