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Chilean wine is having a moment, with vintners discovering the myriad terroirs in the country spanning over 10 latitudes from the Pacific to the Andes--with over two dozen grape varietals. Many of the most avant-garde projects are small producers making garage or even underground wines alongside the reference wines. Enter Santiago Wine Club. The owners, two wine-loving friends (one French, one Chilean), teamed up to bring these inspiring wines to their loyal patrons in Barrio Lastarria. Arranged by valley, their are obscure, fun, serious wines for everyone. Owners are usually at the store and know their wines well. Perfect for any wine lover or drinker to take a bottle home--or drink while in town. Rosal 386, almost corner Victoria Subercaseux, Barrio Lastarria Phone: 56 (2) 2632 6596

Chilean society is quite conservative by many standards with the younger generations finally starting to cut loose. Get more playful. Be expressive. US expat Jayne Morgan saw the opportunity to fill the niche for erotic toys in the capital, starting as private bachelorette parties. The idea was a runaway success and she’s expanded to now have two stories in Providencia and Barrio Lastarria to satisfy the demand. Sex toys, games, outfits, and erotic books, all imported of high quality and good taste, are all laid in her attractive stories with attentive staff. Monjitas 580, 2nd Floor (in Bar The Clinic Building) Phone: 56 (2) 2632 5988

Go Bar occupies an old colonial house on a leafy Mendoza street (formerly Winery & Company). Its old, worn wooden floors speckled with sunlight have just the right vintage feel for wine browsing. It’s several rooms are stacked with wrought iron shelves featuring the region’s numerous wine labels. The staff is friendly and knowledgeable and will give you the perfect packaging to carry wines in your suitcase back home. Chile 898 (corner of Montevideo)

The first luxury lodge to come to Chile’s second biggest island, Tierra Chiloé opened in 2012 and became a member of the Tierra hotel group in 2014. Designed by Chilean architect Patricio Browne, the hotel looks like a boat on stilts and was inspired by the homes of local fishermen, which take the same form and are known as palafitos. The exterior is made from picturesque larch wood shingles—a building technique that’s very typical on Chiloé and is seen on the famous UNESCO World Heritage churches that dot the islands.

Inside, guests find more wood. The hotel’s wood walls and ceilings are made from indigenous species . The decorations are locally inspired with plenty of handicrafts such as wicker baskets, handwoven rugs, and wooden carvings. The focal point is the meadow and Reloncaví Sound below, where the hotel’s boat is harbored. Large windows line the building on both floors and provide excellent views. Guests can relax in a small spa, a winetasting room, or a book-filled upstairs studio upstairs. The living room with fireplace makes a perfect spot for an end-of-day pisco sour.

This little village fuels many a Chilean’s vision of the south—Germanic towns nestled among sapphire-hued lakes—and is often synonymous with summer vacation. Frutillar, just north of Puerto Varas, seems to be straight from Bavaria with its majestic “casonas,” built in the German tradition—a nod to the strong ancestry and settlement in the region. Frutillar’s lakefront has black-sand beaches, the shimmering lake dotted with white swans, magnificent views of the Osorno volcano, manicured lawns, and darling boutiques and cafes along the town’s streets. During the last week of January and first week of February, music lovers flock to Frutillar for the classical music festival where maestros from all over the world play in the Teatro del Lago, with some of the best acoustics in Chile. Besides strolling the relaxed lakefront, Frutillar is perfect to stop for a coffee and “kuchen,” a delectable German cake found throughout the lake district made with seasonal fruit.

In 1998, former Chilean dictator Augusto Pinochet was arrested in England at The London Clinic. A month later, satirical, left-leaning newspaper The Clinic was born. The newspaper’s namesake bar in the Lastarria area, housed in a gorgeous Baroque building, is constantly sporting zingers directed at many Chilean public figures. The Clinic is THE spot in Lastarria to toss back some cocktails or beers among hipsters. Every night it’s slammed. While they put on a weekend brunch and executive menu at lunch, it’s not about the food. It’s the cool scene. Monjitas 578, almost corner Miraflores Phone: 56(2) 2266 4440

This acclaimed ice cream parlor with more than 15 locations (most Santiago malls have one) dishes out every imaginable flavor. Regulars crave dulce de leche, lifted from the namesake caramel dessert. Or try the Chilean classic called café helado, a tall glass of strong, chilled coffee with a scoop of ice cream at the bottom and whipped cream on top. ¡Ay, yi, yi! A rare spot for decaf coffee, as well as sugar-free and gluten-free treats, La Rosa serves breakfast, lunch, and high tea.

Want to try hearty, rustic specialties that are considered true Chilean cooking? Look no further. This sprawling place on the outskirts of the city, in the foothills of the Andes, is a winner. Agustina Gómez de Olivares (aka Doña Tina), now 72, started decades ago selling “pan amasado,” homemade dimpled bread along the road. Years later, the whole family is involved. She’s stickler for seasonality so visit her during the summer months when corn is in season to try the heavenly national dish “pastel de choclo” or “humitas,” fresh corn tamales with basil. However, faithful capitalinos make the schlep east for her baked beef empanadas with juicy stuffing. Camino Los Refugios del Arrayán 15125, Lo Barenechea Phone: 56 (2) 2321 6546

Genuine Magallanes fare such as open-flame, spit-roasted lamb is what you find on the menu at this bucolic oceanside estate on the Eberhard Fjord in Patagonia. Aperitifs in hand, visitors can watch how the flavor-packed food that just keeps coming is prepared, and the service is a paean to Patagonia’s renowned hospitality. Connoisseurs recommend ordering the matambre, an especially tasty cut of beef. Tables hold parties of six or more, and individual diners are seated with whatever group can accommodate them. Reserve on the restaurant’s website (and remember that mobile service can be intermittent in this corner of the planet). Open mid-September to late April.

Located just outside of Santa Cruz in the heart of the Colchagua Valley, Clos Apalta Residence (formerly Lapostolle Residence) is known for its premium Chilean wine. In 2005, the Marnier family opened the stunning property on a steep hillside in the micro region of Apalta. In addition to a state-of-the-art, gravity-fed winery, they built four villas, giving wine lovers a unique place to stay. Today, Clos Apalta functions as a Relais & Chateaux luxury hotel, complete with beautiful views of the valley and its surrounding mountains. Guests can relax on their private terrace, in the lodge, or by the infinity pool, sipping house wines while enjoying the vistas. They also have exclusive access to the dining room, where chefs use produce from the hotel’s own organic garden, and tours of the owners’ wine cellar during visits to the winery.

Liguria is an institution in Santiago. It’s the default for meeting friends and colleagues over chilled draft beers called schops, or dangerously loaded cocktails. The bar scene is animated and starts in the late afternoon around happy hour and ends in the wee hours of the morning. The kitchen pumps out tasty Chilean bistro-style fare ranging from countryside rabbit in mustard sauce to their much renowned “carne mechada,” a braised beef in tomato and red wine chopped up on pasta or sliced down into sandwiches. Get there early to score a table or make friends with the bartender. Best Locations: Metro Tobalaba on Luis Thayer Ojeda & Metro Manuel Montt (address listed here). Photo: Qantas

Founded in 1879, Confitería Torres is Santiago‘s oldest restaurant still functioning, and a popular lunch destination. Housed in the Palacio Íñiguez on the stately Alameda avenue, the restaurant was saved from closing nearly a decade ago and completely restored to its former glory, with green-and-white hand-painted tile floors, lace curtains, and elegant waiters. It’s located near the government palace, and frequented by many politicians and presidents; former president Barros Lucos always ordered a steak and cheese sandwich here (the sandwich was christened with his name). The menu sticks to traditional Chilean cuisine and the bartender whips up some delicious pisco sours. Crowded at lunch time so reservations a good idea. Alameda 1570, Santiago Centro Phone: 56 (2) 2688 0751

A short drive outside the town of San Pedro de Atacama, Tierra Atacama has wonderful views of fields and Volvano Licancabur. The hotel is part of the Tierra hotel group owned by the Chilean-American Purcell family (who also own Tierra Patagonia, Tierra Chiloé, and Ski Portillo). The property originally served as a cattle corral, but Chilean landscape artist Teresa Moller has transformed the grounds, preserving the ancient algarrobo and chañar trees and restoring the adobe walls.

The bedrooms are decorated in natural colors, with local touches like ceramics marching along the sills of the extra-large windows. Animal-skin rugs and alpaca throws provide a touch of warmth for the cool desert nights. You can see the incredible silhouette of Volcano Licancabur from all the rooms, but the Poniente rooms are slightly larger and have better views. There is a friendly communal vibe at the hotel, and upon arrival guests meet with the head guide in the main lounge to choose from the range of group activities on offer each day.

The Aubrey sits at the edge of Barrio Bellavista, a few steps from Santiago’s bottle-green 1925 funicular (which takes visitors up to Cerro San Cristóbal) and just below the zoo (sometimes guests can hear the animals when they’re lying by the pool). Open since 2010, this 15-bedroom boutique hotel is housed between two 1920s mansions built by the same architect. The larger of the two houses once belonged to famed Chilean railway magnate Domingo Durán. Today, the hotel is owned by a Brit and an Aussie who spent $3 million and several years transforming it into its current state.

The bedrooms are split between the two mansions, and there’s also an outside block housing a few pool suites. A cobbled terrace runs between the restaurant and piano bar. The interiors are inspired by the early 20th-century art deco movement and feature statement art deco furniture, printed fabrics, and elaborate wallpaper.

About a two-and-a-half hour drive from Santiago (or 30 minutes by helicopter), Puma Lodge is located in the Andean foothills near the Argentine border. The lodge is part of the Chilean-owned Noi hotel group, which also has properties in Patagonia, Atacama, Santiago, and more. Opened in 2011, Puma Lodge has a ski chalet feel, with wooden interiors and a large fireplace in the middle of the bar and lounge area. The 24 rooms are all the same category, and the design is simple and comfortable with touches such as colorful throws and local artwork.

Many guests choose Puma Lodge for the heli-skiing, but there’s plenty on offer year-round and for the less intrepid traveler. Activities include hiking, horseback riding, or heading out for a picnic lunch by the river. There’s also an on-site spa, yoga studio, and wine cave. Outdoor hot tubs are great after skiing, and a swimming pool is a draw in the summer months.