If you want to experience some of the highlights of Chile but are limited in terms of time, then this brisk five-day jaunt is perfect for you. You'll arrive in the capital of Santiago and explore the city on foot, taking in the major sights. Then it's off to the coast for some wine tasting and an exploration of the most romantic city in the nation: Valparaiso. After a tasty food tour of Santiago, you'll finish your time in the country with a road trip into Chile's central mountains. Enjoy!

Highlights

  • Go wine tasting in Chile's famous Casablanca Valley
  • Tour Valparaiso, the most romantic and artistic city in Chile
  • Discover the flavors of Santiago on a food tour
  • Emabark on an excursion in the mountainous Maipo Valley

Brief Itinerary

Day Highlights Overnight
Day 1 Arrival in Santiago de Chile Santiago
Day 2 Valparaiso, Viña del Mar & Casablanca Valley Santiago
Day 3 A Bite of Santiago Santiago
Day 4 Maipo Valley Full-Day Tour Santiago
Day 5 Departing Santiago  

Detailed Itinerary

Day 1: Arrival in Santiago de Chile

Santiago is an eclectic, artistic, and historic city
Santiago is an eclectic, artistic, and historic city

Welcome to Chile! Upon arrival at Santiago International Airport, a driver will meet you and transfer you to your hotel. You'll have the rest of the day to explore the city at your leisure. 

Suggested activities include:

  • Hike to the top of Cerro San Cristobal, the most magnificent viewpoint in Santiago. When visiting any new city it's a good idea to get your bearings by surveying the area from a high vantage point. Pathways lead 850 meters (2,788 feet) up this central hill to a series of lookouts that offer wraparound views of Santiago. Enjoy the reconnoitering, and if you aren't the hiking type not to worry: you can catch a scenic gondola to the top.

  • Stroll the cobblestone streets of Barrio Bellavista. On the north side of Santiago, you'll find this trendy enclave, at once fashionable and bohemian. Brightly painted old houses adorned with graffiti art sit alongside modern shopping complexes featuring an eclectic array of eateries and bars. It's a great place to come for dinner out, a glass or two of Chilean red, and people watching from a patio table. 

  • Visit the Plaza de Armas, located in Santiago's historic center. There's a lot of history within the four corners of this expansive stone plaza, as it was founded all the way back in 1541. Also here is the impressive Catedral Metropolitana, a neoclassical church dating to 1748 and whose towering twin bell towers dominate the north side of the plaza.

  • Snap pics in front of the Palacio de la Moneda. Chile's opulent Presidential Palace (known simply as "La Moneda") is just a short stroll from the Plaza de Armas, and like the plaza, it's filled with history. It was here in 1973 that Chile's armed forces, backed by the U.S. government, overthrew President Salvador Allende, kicking off a brutal right-wing military dictatorship that would last for 17 years. Today the country is under democratic rule, and visitors are welcome to visit the palace. 

For dinner be sure to get out of the hotel and enjoy a culinary adventure in the city. In recent years Santiago has emerged as a global foodie destination. Chilean chefs are reinventing traditional dishes like empanadas, cazuelas (stews) and seafood with ingredients harvested all the way from the northern deserts and southern Patagonian regions. You can find great restaurants and wine bars not only in the Bellavista neighborhood but also in the revitalized historic barrios of Yungay and Italia.

Day 2: Valparaiso, Viña del Mar & Casablanca Valley

The hills of Valparaiso
The hills of Valparaiso

After breakfast, you'll depart from your hotel in Santiago and drive about an hour west towards the coast. Your destination is the Casablanca Valley, which is home to many top wineries. Here you'll take a tour, tasting, and enjoy lunch at the wonderful Casa del Bosque Winery.

After lunch, you'll continue the short distance to the coast and the cities of Valparaiso and Viña del Mar. First up is the port city of Valparaiso, a UNESCO World Heritage Site famous for its colorful hillside neighborhoods, winding stairways, and abundance of street art. It's a throwback to a time when electric trollies coasted along the waterfront and funicular elevators carried people high into the hills. On a city tour, you'll visit some famous sites, such as Plaza de la Victoria and the Naval Academy, and ride a funicular high into the hills where panoramic vistas of the bay await. A real highlight is visiting the former home of Chile's Nobel Prize-winning poet, Pablo Neruda. 

Afterward, you'll drive a short way to the adjacent town of Viña del Mar, which couldn't be more different in terms of style than its neighbor. Whereas Valparaiso is a retro artistic haven, Viña is a modern seaside hotspot abounding with sleek shopping centers and upscale restaurants. After touring around the city and waterfront, you'll return to Santiago in time for dinner.

Day 3: A Bite of Santiago

Savor some tasty Chilean empanadas on a food tour
Savor some tasty Chilean empanadas on a food tour

Today you'll get out and explore on a half-day food tour of Santiago. It's an immersive experience that reveals the true beating heart of the city, which is found in its people, marketplaces, and cuisine. It's so informative, in fact, that by the end of it, you'll be an honorary Santiaguino. 

Highlights of the tour include:

  • Wandering the aisles of Santiago's labyrinthine central market. This is the beating heart of the city, overflowing with vendors and local residents eager to get their hands on the freshest of the day's produce. With the assistance of an English-speaking guide, you'll engage with these vendors and shoppers, learning about their daily routine while getting the inside track on the most delicious tidbits to try.

  • A tasting of traditional Chilen dishes. It's not enough to experience the kinetic energy of the marketplace—you'll want to do like a local and indulge your taste buds as well. You'll also get a glimpse into how some of Chile's most famous dishes are prepared.

  • Ascend to the top of Cerro San Cristóbal. After the market its time to hop on a cable car to the top of this hill that sits about 300 meters (984 feet) above the city.  Enjoy the 360° panoramas and take plenty of photos, as these are the most incredible views in Santiago.

  • Take a lunch break in the fashionably bohemian enclave in Barrio Bellavista. It's time for even more food, this time in the trendiest neighborhood in the city: Bellavista. Here you'll find a diverse array of funky cafés, international eateries, and high-end restaurants.

After the tour, you will return to your hotel and can spend the remainder of the day relaxing. 

Tour Duration:
Half-day (with English-speaking guide)

Day 4: Maipo Valley Full-Day Tour

The Embalse de Yeso, in the Maipo Valley
The Embalse de Yeso, in the Maipo Valley

Today you'll experience even more of Chile's famous natural beauty with a visit to Cajón del Maipu. After breakfast, you'll embark on a 45-minute road trip southeast of Santiago to this popular gorge. You'll first arrive in the fertile San José de Maipo region, with its hills and vineyards. Then it's an ascent into the mountains and the landscapes become even more dramatic as massifs and snow-capped peaks dominate the skyline. That's to say nothing of the sparkling rivers and streams that wind through this paradise.

After reaching 3,000 meters above sea level (9,843 feet), you'll exit the vehicle at the shores of the Embalse de Yeso, a reservoir nestled in the Andes whose glassy surface shines bright turquoise. There will be ample time to marvel at this landscape and snap photos of the panoramic vistas. You'll also walk around the shore as your expert guide offers insight into the geology of the area as well as the history of the reservoir, a result of damming the Yeso River back in 1964.

For lunch, pull up a seat near the water and enjoy a picnic accompanied by a selection of top Chilean wine. Afterward, you'll return to San José de Maipo and stop in at a local restaurant to try a traditional Chilean empanada. Finally, you'll transfer back to your hotel in Santiago.

Day 5: Departing Santiago

Sunset over Santiago
Sunset over Santiago

It's time to say farewell to Chile. In the morning, you'll transfer from your hotel to the airport in Santiago for your flight back home. ¡Buen viaje!