2 weeks in Chile itinerary

Chile for me is a perfect travel destination. You'll find a staggering variety of landscapes, all stretched across a narrow ribbon of land that runs from the desert in the north to the glaciers in the south. Over the course of this 2 weeks in Chile itinerary, you'll cover over 2,600 miles (4,300 kilometers), experiencing everything from cosmopolitan cities and lush wine valleys to some of the world's most remote wilderness. Here's my guide to creating the best Chile itinerary for 14 days.

Chile itinerary 2 weeks overview

Before we dive in to this Chile itinerary, know this: Chile's geography is as diverse as its weather, so pack wisely. You'll need everything from sunscreen and light layers for the desert heat to a waterproof jacket and warm clothes for the windswept plains of Patagonia.

2 week Chile itinerary overview:

• Day 1: Arrive in Santiago, explore Mercado Central, and enjoy panoramic views from San Cristóbal Hill.
• Day 2: Travel to Valparaíso, explore the city's street art and historic funiculars.
• Day 3: Visit Casablanca Valley for wine tasting.
• Day 4: Explore Maipo Valley, known for its Cabernet Sauvignon.
• Day 5: Fly to Punta Arenas and prepare for Patagonia.
• Day 6-7: Explore Torres del Paine National Park, hike to iconic views and glaciers.
• Day 8: Day trip to Tierra del Fuego, visit King Penguin Park.
• Day 9: Relax in Punta Arenas, optional penguin watching or kayaking.
• Day 10: Fly back to Santiago and explore the city.
• Day 11-14: Travel to Atacama Desert, explore Moon Valley, salt flats, and lagoons.

Our breakdown of this Chile travel itinerary starts with the capital city:

Day 1: Arrive in Santiago de Chile

Santiago is a city that might catch you off guard if you're expecting just another Latin American metropolis. It's got all the buzz of a modern city, but it's also rich in history and charm. You'll find here colonial architecture beside sleek skyscrapers, with the snow-capped Andes looming large in the background.

Once you've settled in, head over to Mercado Central for a real taste of Santiago. The fresh ceviche is a must, and if you get the chance, try a slice of pastel de choclo (corn pie)—it's a treat. In the afternoon, take the funicular up San Cristóbal Hill for some fantastic views of the city and the Andes, especially beautiful at sunset.

Where to stay in Santiago de Chile

For your first night of this Chile itinerary for 14 days, you'll find yourself in Santiago, which has a lot of great neighborhoods to choose from.

• Centro Histórico: The heart of the city, filled with vibrant plazas and landmarks like the Cathedral of Santiago. It's a great spot for first-timers, and it's where I usually stay.
• Providencia: A modern, tree-lined area with great dining and nightlife.
• Las Condes: Upscale, with luxury shopping and fine dining, plus easy access to ski resorts.
• Bellavista: A colorful, artsy neighborhood with street art, lively nightlife, and a creative vibe.

Day 2: Travel to Valparaíso

Travel time: 1.5 hours by bus or car from Santiago

Valparaíso is a coastal city full of character. The hillside is dotted with brightly painted houses, and the narrow streets are lined with murals, quirky cafés, and local art. It's a city alive with music, street performers, and artists of all kinds.

Where to stay in Valparaíso

For this Chile 2 week itinerary, you'll spend a night in Valparaiso, and you have a lot of fantastic districts to choose from:

• Barrio Puerto: Located between Plaza Wheelwright and Plaza Sotomayor, this historic area features the Mercado Puerto and Iglesia de la Matriz. It's known for its vibrant atmosphere and cultural significance.
• Plan de Valparaíso: The flat part of the city where public and commercial buildings are found, distinguishing it from the hills (cerros) where the majority of the population live.
• Cerro Alegre: A picturesque hill offering colorful houses, art galleries, and panoramic views of the city and harbor. It's a UNESCO World Heritage site known for its bohemian charm.
• Cerro Concepción: Adjacent to Cerro Alegre, this hill is renowned for its historic architecture, vibrant murals, and lively cafes, providing a quintessential Valparaíso experience.

Things to do in Valparaíso

The best way to explore Valparaíso is by riding one of its historic funiculars (ascensores), so be sure to have some coins ready for the ride.

For a deeper look at the city, join a free walking tour starting from Plaza Sotomayor. It's a great way to get an intro to the area's street art and history.

When hunger strikes, try chorrillana, a delicious dish made of fries, meat, and eggs—perfect for a satisfying meal. For some of the best views, head to Paseo Yugoslavo or Cerro Alegre. Both spots offer great panoramas of the city and the Pacific Ocean.

Day 3: Day trip to Casablanca Valley

Casablanca Valley is Chile's answer to Napa Valley, where cool ocean breezes create the perfect conditions for world-class white wines and Pinot Noir. This Chilean young wine region has rapidly gained international acclaim for its crisp Sauvignon Blancs and Chardonnays. What makes it so special? It's the cool Pacific winds that sweep through here, creating the perfect conditions for white wines.

What to do in Casablanca Valley

Casablanca's small family-run wineries are where the real magic happens.You'll get more intimate experiences at the smaller wineries, where you'll be able to pair the wines with local cheeses and olive oils. One standout is Viña Casas del Bosque, known for their exceptional Sauvignon Blanc and Pinot Noir. Another gem is Viña Emiliana, one of the region's pioneers in organic and biodynamic wines.

Forget about driving yourself — hire a guide who knows the area and can take you to the hidden gems.

Day 4: Day trip to Maipo Valley

If Casablanca is Chile's new kid on the block, Maipo Valley is the seasoned veteran. This is where Chile's wine history began, and it remains one of the country's most revered regions, especially for its exceptional Cabernet Sauvignon.

The valley is often referred to as the "Bordeaux of South America" for good reason — its rich, mineral soils produce wines that have consistently wowed critics around the world. You could easily plan an Chile itinerary just coming here alone.

What to do in Maipo Valley

Start your day by exploring the historic cellars at Viña Concha y Toro, one of Chile's largest and most iconic wineries. While it's a popular spot, the historic underground cellars and the famed Casillero del Diablo make it a must-see. If you're after something more intimate, Viña Undurraga provides an excellent experience with a focus on traditional winemaking techniques combined with modern flair.

Day 5: Travel from Santiago to Punta Arenas

Travel time: 3.5 hours by flight

Punta Arenas will be your base to explore Patagonia, so make sure to book your flight early from Santiago to get the most out of your time in the south. This city, perched on the edge of the Strait of Magellan, feels like the gateway to another world. After the lush vineyards and sun-soaked wine regions, Punta Arenas marks the beginning of an entirely different adventure — one filled with glaciers, towering peaks, and remote wilderness. It's the place where your journey into Patagonia begins.

Upon arrival, take a leisurely stroll through the city center. Don't miss the Ovejero Monument, apparently rubbing the statues toe brings good luck. Also be sure take the opportunity to stock up on any outdoor gear you might need as the prices are higher in more remote areas.

Where to stay in Punta Arenas

For day 5 of this 2 week Chile itinerary, you will stay in Punta Arenas, which has a few nice districts to choose from:

• Centro: The city's heart, bustling with shops, restaurants, and key attractions like Plaza Muñoz Gamero. A lively area perfect for exploring the city's culture. Personally my favorite.
• Barrio Sur: A peaceful, residential area south of downtown with parks, schools, and stunning views of the Strait of Magellan. Ideal for families.
• Barrio Norte: A northern district known for its green spaces, recreational areas, and proximity to the University of Magallanes. Popular with students and academics.
• Barrio Croata: A charming neighborhood influenced by Croatian immigrants, featuring beautiful parks, cultural events, and a strong sense of community.

Day 6: Day trip to Torres del Paine

Torres del Paine National Park is absolutely stunning, a place where nature's raw power and beauty take center stage. As a UNESCO Biosphere Reserve, it's one of the most famous spots in Patagonia. The park is named after its iconic granite towers, which rise dramatically into the sky The park's name comes from these towers – "Torres" meaning towers, and "Paine" derived from an indigenous Tehuelche word for blue. This is one of many great parks in Chile.

Places to see

Mirador Las Torres offers the park's most iconic view, a tough trek leading to a spot where the three towers reflect in a glacial lake below. Start early, around 7 AM, to avoid the fierce afternoon winds. The path takes you through ancient forests and across glacial moraines before the towers come into full view.

At Grey Glacier, you'll see a massive 4-mile-wide ice wall, part of the Southern Patagonian Ice Field. This is one of the largest ice masses outside the poles, and its scale is truly humbling. A boat tour brings you up close to the glacier, where huge chunks of ice break off and fall into the lake. For the best views, head to the left side of the boat, where you can take in the full glacier with the mountains in the background.

Day 7: Another day of exploring Torres del Paine

The French Valley is a true natural wonder, shaped by ancient glaciers and nestled between the towering peaks of Paine Grande and Los Cuernos. As you hike deeper into the valley, you'll likely hear the roar of avalanches as ice breaks away from the glaciers above.

Places to see

Lake Pehoe earns its reputation as the park's most photogenic lake. Its turquoise waters perfectly reflect the surrounding mountains, especially early in the morning when the lake is calm. The striking color comes from fine rock flour carried down by glaciers above.

The Base of the Towers trek is the park's highlight—an 8-hour round trip that offers a serious challenge and a huge reward. The trail takes you through dense lenga forests, across crystal-clear streams, and up a steep moraine, all leading to a breathtaking viewpoint of the three towers rising from a glacier-fed lake. Even if you only do the first section through the Ascencio Valley, you'll still be treated to some of Patagonia's most incredible scenery.

Day 8: Tour to Tierra del Fuego

On day 8 of this 14 day Chile itinerary, you'll head to the legendary "End of the World," an archipelago that's been capturing explorers' imaginations since Magellan first sailed these waters: Tierra del Fuego. This remote area is one of the southernmost inhabited places on Earth, where the South American continent breaks into a maze of islands and channels.

Places to see

In Porvenir, you'll want to take the chance to visit the local museum. Learn about the Selk'nam people, whose deep connection to this rugged land shaped their way of life, and discover how the gold rush transformed the area.

King Penguin Park is a highlight, home to the only king penguin colony outside of Antarctica. Visit early or late in the day when the penguins are most active, and you'll see their courtship and feeding behaviors up close as they waddle between their nests and the shore.

The ferry ride to Tierra del Fuego is an adventure in itself, offering chances to spot albatross, petrels, and even whales. But be aware, the meeting of the Atlantic and Pacific currents can make the waters choppy, so it's a good idea to bring motion sickness pills!

Day 9: Relax and unwind

Take a free day in Punta Arenas to explore at your own pace. If you're up for some adventure, head to Magdalena Island in the morning to see one of the largest Magellanic penguin colonies in southern Chile. Thousands of penguins nest here from September to March, and the early hours are the best time to watch them in action. The boat ride offers great views of the Strait of Magellan and you might spot seabirds and marine mammals along the way.

For a more laid-back option, visit the Cerro de la Cruz viewpoint, especially beautiful at sunset. From here, you'll get a great view of Punta Arenas with the mountains and strait in the background, as the sky lights up in stunning colors.

If you're into kayaking, explore the Strait of Magellan. You can paddle past historic sites, and keep an eye out for seals and dolphins, especially recommended with experienced guides leading the way.

Day 10: Fly back to Santiago

Head back to Santiago with a fresh perspective and a deeper appreciation for Chile. You want to use this day to take it easy and to explore parts of the city you might have missed during your first visit.

Things to do in Santiago

Start your day in the Lastarria neighborhood.This artsy area is full of life, with tree-lined streets filled with independent galleries, boutique shops, and cozy cafés. While you’re wandering, grab a traditional mote con huesillo—a refreshing Chilean drink made from sweet peach nectar and husked wheat, commonly sold by street vendors.

To dive deeper into Chile’s cultural heritage, visit the Museum of Memory and Human Rights, which offers a powerful and thoughtful look at Chile's recent history. 

Day 11: Travel to San Pedro de Atacama

Travel time: 2-hour flight to Calama, then 1-hour drive

Enter the driest non-polar desert in the world, where some weather stations have never recorded rainfall. San Pedro de Atacama, an ancient oasis town, has sheltered travelers for over 11,000 years. Today, it welcomes astronomers, adventurers, and those seeking otherworldly landscapes. At 2,400 meters above sea level, the town's adobe buildings and narrow streets feel like stepping into another time.

The stark beauty of the Atacama Desert reveals itself immediately - rust-colored mountains against brilliant blue skies, salt flats that shimmer like mirrors in the distance. When you arrive, take time to adjust to the altitude with a cup of coca tea at one of the courtyard cafés. The town's Plaza de Armas comes alive at sunset when the day's heat subsides, and local artisans set up their stalls.

Where to stay in San Pedro de Atacama

On day eleven of this Chile trip itinerary, you have the choice to stay in one of the few towns of San Pedro de Atacama.

• Centro: The heart of San Pedro, Centro features the main shopping areas, attractions like the Iglesia San Pedro de Atacama, and the Museo del Meteorito. The pedestrianized Caracoles Street is lined with restaurants and tour agencies.
• Toconao: A quaint village located 24 miles (38 km) south of San Pedro de Atacama, Toconao is known for its historic church with a bell tower dating from 1750.
• Socaire: Situated 61 miles (100 km) southeast of San Pedro, Socaire offers views overlooking the Salar de Atacama. The local economy is dominated by agriculture and non-metallic mining.
• Catarpe: A rural area near San Pedro de Atacama, Catarpe is known for its agricultural terraces and traditional adobe houses. It's a peaceful retreat offering a glimpse into local life.

Day 12: Visit the Moon Valley

Valle de la Luna (Moon Valley) lives up to its otherworldly name, and it's no coincidence that NASA tested their Mars rovers in this landscape. The valley's dramatic rock formations, salt caves, and rolling dunes create an environment so lunar-like that standing among them feels like visiting another planet.

The best time to visit is late afternoon, when the setting sun really brings the place to life. As the light changes, the mineral-rich rocks shift through shades of red, purple, and gold. Stick around after sunset for some of the best stargazing you’ll find anywhere. The high altitude, clear desert air, and minimal light pollution make for perfect conditions to see distant galaxies, nebulae, and planets.

Day 13: Explore Atacama Salt Flats & Miscanti Lagoon

Start your final day of this Chile itinerary for 14 days in the desert with an early visit to the Atacama Salt Flats. These vast, crystalline expanses were formed by ancient evaporated lakes, creating one of the most surreal landscapes on Earth. At Laguna Chaxa, you’ll see flocks of flamingos feeding in the shallow waters, their pink plumage standing out against the white salt crust. The early morning light adds a magical touch as the flamingos’ movements create reflections in the water.

Next, head to Toconao, a traditional village where locals have used volcanic stone for centuries to build homes and the San Lucas bell tower. The village's ancient irrigation systems and terraced gardens show how people have adapted to desert life.

Finish at Miscanti Lagoon, a stunning high-altitude lake surrounded by volcanoes. At 4,200 meters above sea level, the deep blue water contrasts with the surrounding landscape. Keep an eye out for vicuñas and Andean foxes.

Day 14: Travel back to Santiago

Your final day takes you through the end of a journey across some of Chile's most diverse landscapes. As you leave the Atacama Desert, you'll pass by the salt flats and volcanic peaks one last time. The contrast between Santiago's metropolitan valley and the remote desert areas you've explored highlights the variety of landscapes in Chile, from dry deserts to icy regions.

That sums up this Chile itinerary for 14 days. If you don't quite have two weeks for Chile, be sure to see our 10 day Chile itinerary.

If you want to skip the hassle of planning and booking, you can have one of our local travel experts plan your trip for you. Our tailor-made trips service takes care of every detail for you and is completely customizable.

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