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  • Writer's pictureLauren H

Two Weeks in Chile



Hike across stunning landscapes in Patagonia, kayak amongst glacial icebergs, visit penguins in the wild, explore famous landmarks in Santiago, sample organic wines, and take in the street art of Valparaiso, all within two weeks in Chile.


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Day One and Two: Santiago

For two days in Santiago, I have outlined our favorite activities below. Fit in as much or as little as you want!


Cerro Santa Lucia- This is a park, hill, and historic site all in one.  It’s a great stop for getting some steps and a view in, with the added bonus of a beautiful Neptune fountain and ornate stairways. 


A Fountain at Cerro Santa Lucia
A Fountain at Cerro Santa Lucia

Cerro San Cristobal-This another park and hill, but much larger than Cerro Santa Lucia. There is a Funicular that takes you to the top, but hiking trails are also available if you prefer to walk. Near the top is a Statue of the Virgin Mary and a small chapel. The Chilean National Zoo is also located in this park. Cerro San Cristobal felt much more touristy than Cerro Santa Lucia, but the views from the top were better. 


Riding the Funicular at Cerro San Cristobal
Riding the Funicular at Cerro San Cristobal

Walk or Bike Around the Bellavista Neighborhood- The Bellavista area (near Cerro San Cristobal) is known for its vibrant street art and local bar and restaurant scene.  It’s a picturesque neighborhood to explore. 


Street Art in Bellavista
Street Art in Bellavista

Walk and Shop Around the Streets in Lastarria-This area also has a lively restaurant and cafe scene as well as street artists and vendors. Start walking near the Museo de Artes Visuales; you will find many street artists. 


Walking around Lastarria
Walking around Lastarria

Plaza De Armas de Santiago- No trip to a South American city is complete without a trip to the local Plaza De Armas. During the day, this Plaza had many artists and vendors set up as well. 


Cascada de las Animales-Horseback riding in Maipo Valley is a popular activity for visitors in Santiago. We visited Cascada de las Animales and enjoyed a half-day horseback ride in the mountains. It felt like a traditional Chilean experience. 


Horseback Riding in Maipo Valley
Horseback Riding in Maipo Valley


Day Three: Fly to Punta Arenas

Note that even if you aren’t interested in a multi-day trek, it is still absolutely worth flying to the Patagonia region. There are shorter day-hike options, horseback riding tours, penguin tours, boat tours, spas, and more that can fill your days. The landscapes of Patagonia are like nowhere else in the world. 


Day Four: Penguin Tour

From Punta Arenas, we took the day trip to Magdalena Island (via boat) to visit one of the largest nesting sites for Magellanic penguins. I have seen penguins in other parts of the world, but this experience was unique. The penguins run the whole island. Tourists can walk on a path around the island and see penguins interacting with one another, caring for their young in their nests, talking to each other, and more. It was worth the excursion. Note that it can be windy and chilly on the island, so dress accordingly! We also learned that any tours that depart after early morning have a high liklihood of being cancelled. The winds tend to pick up later in the day and they will cancel the boat rides due to the wind conditions. Be sure to book one of the early morning departues.


Photographing penguins on Magdalena Island
Photographing penguins on Magdalena Island

Penguins on Magdalena Island
Penguins on Magdalena Island

Day Five: Punta Arenas and Transfer to Puerto Natales

If you have time in the morning, explore Punta Arenas before departing for Puerto Natales. Costanera del Estrecho is a 7-mile waterfront walkway with sculptures, beaches, and artwork that is worth a short walk. Note it will be very windy (the whole town is!). 


Walking on Costanera del Estrecho
Walking on Costanera del Estrecho

I also recommend walking up to the viewpoint at Cerro De La Cruz to take in the colorful views of the city from the top of the hill. Nearby Cafe Sarmiento makes a great lunch spot as well. 


Views of Punta Arenas
Views of Punta Arenas

In the afternoon, we took a bus to Puerto Natales. Hiring a driver or renting a car are also options for getting to Puerto Natales. It is a 3-hour drive. 


Day Six: Bus to Tores Del Paine and Start the W trek

See my post here for information on planning for the W Trek and here for information on each day of the trek. 


Day Seven: The W Trek

Day Eight: The W Trek

Day Nine: Kayak Gray Glacier Lake, bus back to Puerto Natales


We kayaked at the end of our W-Trek hike, but there are options for glacier kayaking and glacier treks for visitors not doing the W-Trek. Check out Big Foot Patagonia for more information. It was an other-worldly experience kayaking around icebergs that had broken off of the glacier. They provide all of the gear and clothing you need.


Kayaking near Gray Glacier
Kayaking near Gray Glacier

Day Ten: Explore Puerto Natales


We wanted to plan for a rest day after all the hiking, but we also wanted a day to explore Puerto Natales. It is a picturesque mountain town with many unique art galleries, shops, and restaurants. A few of my favorite spots in town are listed below. 


Muelle Historical- Puerto Natales is famous for this historical pier. It was a fun spot to take photographs with the ever-changing Patagonian sky behind it. 


Muelle Historical
Muelle Historical

Pueblo Artesenal Etherh Aike- This was a nice stop for buying locally made wool goods and other souvenirs. It felt pretty touristy, but it still had a decent selection of vendors.


A small store in Pueblo Artesenal Etherh Aike
A small store in Pueblo Artesenal Etherh Aike

Cafeteria Nandu- This was a cafe/souvenir shop.  At first glance, it seems like the store only has cliche travel souvenirs, but ticked in the back was a section of art and clothing made by local artist Jorge Caballero.


Artwork by Jorge Caballero
Artwork by Jorge Caballero

Espacio Artesanal- This was another artists' market with small mini spaces showcasing various artists.  This market had more actual paintings, carvings, and art than Pueblo Artesenal Etherh Aike.


Espacio Artesanal
Espacio Artesanal

Ls Tehuelch- This store focused on woven goods.  It was more expensive than the stores mentioned above, but walking through to see woven wall art, pillows, blankets, and more was still fun. 


Day Eleven: Bus to Punta Arenas, Fly to Santiago


Day Twelve: Casablanca Wine Valley

For this portion of the trip, we hired a driver to drive us to Casablanca, Valparaiso, Vina Del Mar, Colchuga Valley, and then back to Santiago.  It would also be easy to rent a car and take a road trip on your own. The roads were well-marked and in good condition. 


The Casablanca Wine Valley is a younger wine region in Chile. My favorite vineyards in the area are outlined below.


Casa Valle Vinamar- This vineyard is known for its sparkling wines. The wines were good, but I think visiting the picturesque grounds and restaurant makes it worth the visit.  The lunch was delicious as well. 


Walking around the grounds at Casa Valle Vinamar
Walking around the grounds at Casa Valle Vinamar

Views from Casa Valle Vinamar
Views from Casa Valle Vinamar

Bodega RE- Our driver recommended this small, boutique vineyard to us, and we loved it.  We both bought multiple bottles to bring home and hope they will ship to the States someday.  They make numerous natural wines that are made in clay pots rather than wood barrels. Some of their wines are still made with grapes crushed by feet. 


Clay pots at Bodega RE
Clay pots at Bodega RE

Casas Del Bosque-The wines weren’t particularly memorable here, but the lunch at Casa  Mirador was.  The restaurant is atop a small hill and beautifully designed to showcase the surrounding views. 


The lunch table at Casa Mirador
The lunch table at Casa Mirador

Day Thirteen: Valparaiso + Vina Del Mar

Valparaiso and Vina Del Mar are large cities near Santiago and easy to add on as part of a road trip around wine country. The two cities couldn't be more different. Vina Del Mar is a beachside resort town that is very crowded. There is a long walkway along the oceanfront and multiple beaches to explore. It felt like many other European beach towns.


Vina Del Mar
Vina Del Mar

Vina Del Mar was so crowded it would discourage me from visiting again. If you want to squeeze in a beach day, it's a nice spot, but I would recommend more time in Valparaiso instead. Although the two look close on a map, the traffic between them can make traveling between the two cities difficult.


Valparaiso is a vibrant, artistic city built up on a hillside along the water. Multiple funiculars throughout the city can take you to various viewpoints of the colorful buildings below. There are also numerous well-known artistic landmarks, such as the piano staircase. We enjoyed wandering the streets to pop in art galleries, cafes, and restaurants while taking in the street art along the way.


A colorful staircase in Valparaiso
A colorful staircase in Valparaiso

A View of Valparasio's Colorful Buildings
A View of Valparasio's Colorful Buildings

Looking down a street in Valparaiso
Looking down a street in Valparaiso

Day Fourteen: Colchagua Valley Wine Tasting


Colchuga Valley is arguably Chile's most well-known wine region and is only a short drive from Santiago. A couple of my favorite vineyards in the area are listed below.


Casa Silva is a larger wine producer that ships their wines worldwide. It was interesting to tour a larger vineyard and its grounds, but we also really enjoyed their wines, especially their Carmenere varieties.


This vineyard is a perfect spot for viewing the sunset. It is set higher in the mountains, so you can enjoy views down in the valley while enjoying a wine tasting and charcuterie board.  They offer live music at sunset some nights of the week as well. 


Views at Vina Ventisquero
Views at Vina Ventisquero

What to Eat


Empanadas- 

Like the rest of South America, Chile has its own take on an empanada. I loved the flaky puff pastry exterior we found on Chilean empanadas.


A Chilean Empanada
A Chilean Empanada

Calafate Anything!-

Calafate berries are a fruit that is only found in the Patagonia region.  They look like a blueberry but are more flavorful. We found them used in drinks and desserts.  A Calafate Sour is a commonly found drink in the area; it's a pisco sour with added berries. We only found one Calafate Spritz, a take on an Aperol Spritz, but the one we had was amazing.


A Calafate Spritz
A Calafate Spritz

Pebre-

This sauce is Chile’s take on a salsa or chimichurri. It is often served with bread, grilled meats, or empanadas. It consists of onions, tomatoes, oil, parsley and spices. 


Pebre with Bread
Pebre with Bread

Dulce De Leche-

A Thick caramelized milk that is found in all kinds of desserts throughout Chile. When you see a pastry that includes dulce de leche, you can't go wrong, try it!


Brazo de Reina-

A traditional Chilean rolled sponge cake filled with dulce de leche.  It is simple but delicious!


Brazo de Reina
Brazo de Reina

Milhojas or Thousand Layers Cake-

This cake (and sometimes a pastry) contains very thin layers of dulce de leche and then layers of cream and/or fruit.


Milhojas (or Thousand Layers Cake)
Milhojas (or Thousand Layers Cake)


Where to Eat


Santiago


They offer counter-service traditional Chilean empanadas. The restaurant has been around since 1930.  Beware, the empanadas are large!  


Emporio Zunino
Emporio Zunino

A picturesque cafe set inside a castle from 1910 within the Parque Forestal. They offer seating in the beautifully decorated interior or outside in the park. The menu offers simple dishes, but the food was fresh and cooked perfectly. It’s worth a visit just for the setting. 


Castillo Forestal
Castillo Forestal

Puna Arenas


Cafe Sarmiento- This quaint cafe sits on a hill overlooking the water and the colorful town. The food and coffee were delicious, and the views made it perfect. Sit upstairs if you can!


Coffee and Views from Cafe Sarmiento
Coffee and Views from Cafe Sarmiento

Puerto Natales


Hotel Kau Cafe-

The baked goods here were amazing. The dining area also had great views and friendly fellow hikers. We ate here a couple of times. 


The Singulair Hotel-

I highly recommend dining at the Singulair Hotel if you feel like splurging. The hotel is in a converted cold storage plant with stunning sunset views. They serve elevated Chilean dishes. 


The bar area at the Singulair Hotel
The bar area at the Singulair Hotel

Santa Cruz


Restaurant VIVA ANTONIO Parrilladas-

This restaurant is located near Casa Silva, along the route between Santa Cruz and Colchuga Valley. It is not in Santa Cruz.  It was one of our favorite restaurants during our two weeks in Chile. The owner and his wife grill to order all parts of the cow, each piece perfectly cooked and seasoned. The service was outstanding as well. 


The owner of Restaurant VIVA ANTONIO Parrilladas
The owner of Restaurant VIVA ANTONIO Parrilladas

Where to Stay


Colchuga Valley (Wine Country)


For a unique lodging experience, consider staying at this boutique hotel in a vineyard. It is outside Santa Cruz, the town in the heart of Colchuga Valley, but it is worth the drive.  It is also conveniently located between Santa Cruz and Santiago, so it’s a nice overnight stop to break up the driving. There are only a few rooms in the hotel, which was formally the family’s home.  It was built in the mid-19th century. The service was outstanding, and the hotel manager went above and beyond to help us with anything. They offer bike rentals to bike around the property as well. The trails through the vineyards would also make a picturesque running route. 


The entrance to Hotel Casa Silva
The entrance to Hotel Casa Silva

Exploring the grounds around Hotel Casa Silva
Exploring the grounds around Hotel Casa Silva

Puerto Natales


The Singulair Hotel-

Staying here isn’t the most budget-friendly option, but the property is stunning. The hotel is in a converted cold storage plant. Every room has water and sunset views. 


Views from a room at The Singulair Hotel
Views from a room at The Singulair Hotel

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