The GAM is one of Santiago's most exciting new cultural centers, and it acts as a default meeting point for tourists and locals due to its central location on the Alameda, in Barrio Lastarria. Opened in 2010 in a strikingly renovated behemoth of a building (originally built by President Salvador Allende in 1972 for the international trade summit UNCTAD), the building now bears the name of Chile’s most celebrated female poet, Gabriela Mistral, the first and only woman to win a Nobel Prize in Literature to date. Permanent exhibits include an in-depth collection of pre-Colombian crafts and artifacts, and visiting exhibits often feature contemporary artists with ties to underground urban movements. The GAM also has an excellent wine shop, a bookstore specializing in Chilean art, design and film, a café and a restaurant open for lunch and dinner.

Like a miniature version of Cerro San Cristóbal, Santa Lucía offers sweeping views of the city and a more manageable hike. The hill, which is nestled between the Lastarria and Bellas Artes neighborhoods just north of the Alameda, is lovely and features Gothic balustrades, cobblestone walkways and lush vegetation. The hill was named by Pedro de Valdivia for the saint day which coincided with his arrival in Santiago, and it was initially the site of military fortresses and a strategic lookout point to anticipate attacks by the native Mapuche Indians. The Castillo Hidalgo on the peak of the hill provides one of the best panoramic views of Santiago. Time your visit accordingly to hear the thunderous boom of a canon that has sounded every day at noon since 1825. Elevator access available.

In the early 1900s, CJ Kingston left his home in Michigan to search for gold in Chile, and while he never found the mother lode, his journey led him to the acquisition of a cattle ranch in the Casablanca Valley. Five generations later, his descendants continue to show the same pioneering spirit through the exploration of new frontiers in Chilean winemaking. Kingston Family specializes in handcrafted, sustainably grown Pinot Noir, Syrah, Sauvignon Blanc and Chardonnay from their vines in the western side of the valley. A visit to this family-run winery begins the moment you turn off a remote country road in Casablanca onto their hidden palm drive. End an intimate tour of the beautifully landscaped premises with a private tasting on their terrace with a view. Reservations are required.

Santiago’s Mercado Central is a majestic little market located in a bustling part of the city, one of the last remnants of an age when passenger trains pulled in and out of the Estación Mapocho and the grand Cal y Canto Bridge spanned the Mapocho River across the way. The wrought-iron structure of the building, which has been declared a national monument, was designed and constructed in England before being shipped over and assembled in Chile. Its first home was the Plaza de Armas, the historic center of Santiago, but it was moved to its current location as the city grew. These days the Mercado Central has been overshadowed in size and volume by the sprawling La Vega market on the far side of the river, but it remains a quaint and accessible venue where first-time visitors can experience the natural bounty that Chile has to offer. Discover the tastes and textures of sea urchin, piure and shellfish of all shapes imaginable in the small fish market before heading inside for a proper Chilean meal.

This winery—about an hour-and-a-half drive west of Santiago—was founded by Pablo Morandé, who was a pioneer in the Casablanca Valley. Morandé was the first to see the valley's vast potential for whites, Pinot Noirs, and cool-climate Syrahs. The winery has a newly built wine tasting salon and a shop selling wines from all around the region (even those not made by Morandé), as well as gifts, books, gourmet food products, and wine-related accessories. Their restaurant, House (Ruta 68, km. 61, Casablanca; 56 32 275 4701), is outstanding and offers a wine-pairing menu.

After both his parents passed away, Jorge Yarur Bascuñan turned his family’s home into a fashion museum showcasing more than 7,000 pieces of clothing, accessories, textiles, decorative arts and sports articles previously owned by Bascuñan’s mother and father or acquired at auction over the past decade. Yves Saint Laurent, Jean-Paul Gaultier, Vivienne Westwood and Chilean designers Marco Correa and Octavio Pizarro are among the famous names represented; dresses and outfits worn by Princess Diana, Madonna, Clark Gable and Marilyn Monroe are also on display.

Although Santiago’s Museum of Visual Arts is a relatively small institution, it is not one to be overlooked due to its outstanding exhibits of contemporary Chilean and international artists. Opened in 2001, the museum has accrued an impressive collection of works from Chilean artists including the celebrated surrealist Roberto Matta and the contemporary Nicolás Franco. Laid out on four separate floors, MAVI features exhibits from its permanent collection along with the works of an established Chilean artist, a visiting show by an international artist and a young or emerging artist. There is a small store with books and arts and crafts, and a neighboring café.

Built in 2006 on a site between the Palacio de la Moneda—the beautiful neoclassical building that once served as a mint, then the presidential palace, and now houses the presidential offices—and Avenida Libertador Bernardo O’Higgins, better known as “the Alameda,” this subterranean cultural center hosts exhibitions, a national film archive and the excellent Artesanías de Chile, an expansive crafts shop and showcase. Look for the entrances on either side of the "plaza" and head down the stairs.

The Palacio de Bellas Artes (Fine Arts Museum) and the Museo de Arte Contemporaneo (MAC) are housed together in a regal, Beaux Arts edifice that was inaugurated on the eve of Chile's centennial independence day in 1910 (the museums have separate entrances at the back and front). The two institutions hold Santiago's largest collection of contemporary art and serve as a venue for the country's most important temporary exhibits. The palace has a noteworthy glass cupola that softly lights a vast lobby, and the facade and interior layout were modeled after the Petit Palais of Paris, making the museum worthy of a visit for the lovely architecture alone. MAC opened in 1947 as an extension of the University of Chile art program and has grown its permanent collection to over 2,000 works since. Its goal is to operate as a pluralistic entity that strives to highlight a wide range of art depicting the cultural diversity found in Chilean society. The Fine Arts Museum hosts major shows by well-known international artists such as Damian Hirst.

The Parque Metropolitano, a city park that is larger than New York's Central Park, sits on the western edge of Providencia. Take the historic funicular to the top of the San Cristóbal Hill, or walk up one of the park's many trails and roads, for dazzling views of Santiago and the Andes. Families can stop off at the Jardin Zooogical, the city zoo, and then reach the summit where a 45-foot-tall statue of the Virgin Mary stands watch over Santiago. The park is home to botanical gardens that represent nearly all the flora found along the length of Chile. Note that on a smoggy day, the obstructed views are not worth the trip to the top.

Like most Latin American countries settled by the Spanish, Santiago was built around one large central square, the Plaza de Armas. This is where the first colonizers ruled, resided and fraternized, and the city’s grid layout radiated out from this point. These days the hustle and bustle of cars and pedestrians as well as frequent construction projects fill the air, but step inside the Santiago Metropolitan Cathedral for a moment of quiet reflection and to admire the neoclassical architecture and elaborately decorated altars. The cathedral is the fifth church to occupy its location since the arrival of the Spanish and was completed in 1800. Other important buildings surrounding the square include the central Post Office, the newly renovated National History Museum and the government building first used to house the Cabildo, the King’s representative governing body in Chile.

Acclaimed Chilean poet Pablo Neruda had three homes in his native country, which have been made into museums. Neruda was a widely traveled diplomat, an obsessive collector and a prolific poet, and a tour through this home, La Chascona, features anecdotal treasures and art that bring to life the singular nature of Neruda, and the political environment during his time. Neruda built the house in 1953 to honor his secret lover and later third wife, Matilde Urrutia, whom he called la chascona, which translates to “the uncombed.” Tours do not need to be reserved, and there are audio guides in Spanish and English.

About a 90-minute drive west of Santiago lies the coastal town of Valparaíso. Because Santiago sits inland, this city on the sea emerged in the late 1800s as Chile’s primary shipping port, and benefitted financially from an influx of wealth. Built on 45 hills, the town’s Victorian houses—painted in every color of the rainbow—create a picture-perfect setting and extraordinary views of the coastline and dockyards. The colorful architecture and hillside setting, along with its laid-back nature and numerous cafés and restaurants, combine to make the city feel like a South American version of San Francisco. Little has been changed or renovated since the heyday of the 19th-century (once the Panama Canal was completed, Valparaíso’s ports were not as crucial) and the town is charming, in a scrappy kind of way. Walls are covered with beautiful and vibrant graffiti, representing everything from pithy cultural references to what could be considered works of art. As a lively student town, Valparaíso has a fun and energetic nightlife. In reply to the question of “when do bars close?” most locals will answer, “when the candles burn down.”

Funiculars, dating back to the 1880s, still carry people up and down the steep hills, though the women of Valparaíso are rumored to have “the most beautiful legs in the world” from the constant exercise. Strolling the rambling pathways of Valparaíso, breaking for lunch at one of the lauded restaurants like Pasta e Vino (Calle Templeman 352, Cerro Concepción; 56 32 249 6187), is a lovely way to spend a morning before an afternoon of wine tasting in the nearby wineries. If visitors would like to spend the night in Valparaíso, there is the Relais & Chateaux property Hotel Palacio Astoreca (hotelpalacioastoreca.com), a boutique hotel with stunning views of the coastline and a magnificent restaurant Alegre, headed by ex-El Bulli chef, Francisco Araya. It is housed in a renovated Victorian mansion and sits across from the also newly renovated fine arts museum, Museo Baburizza (www.museobaburizza.cl). Pablo Neruda’s home La Sebastiana (Ferrari 692; 56-32-225-6606), with its boat-like structure and dazzling views of the bay, is a perennial favorite, and is situated on Cerro Bellavista.