Spend two weeks traveling in luxury as you explore the Chilean side of Patagonia—South America's ruggedly beautiful southern cone. This journey ticks all the highlights, from cruising the Magellan Strait to horseback riding in the Andes and trekking around the granite peaks of Torres del Paine National Park. Rounding out this memorable itinerary are wine and city tours in Santiago, plus hiking to volcanoes and visiting penguin colonies in Chile's captivating Lake District.


  • See the best of Santiago and taste fine wines in the Casablanca Valley
  • Zip along Patagonia's famous Strait of Magellan in a Zodiac
  • Embark on some of the most scenic hikes in Torres del Paine
  • Tour penguin colonies, volcanoes, and charming towns in the Lake District

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Santiago, Afternoon City Tour Santiago
Day 2 Casablanca Valley Wine Tour Santiago
Day 3 Fly to Punta Arenas, Historic Walking Tour Punta Arenas
Day 4 Wildlife Boat Tour on the Magellan Strait Punta Arenas
Day 5 Transfer to Puerto Natales, Lago Sofia Horseback Ride Puerto Natales
Day 6 Transfer to Torres del Paine, National Park Tour Torres del Paine
Day 7 Self-Guided Hike to Las Torres Torres del Paine
Day 8 Self-Guided Hike Along Lago Nordenskjöld Torres del Paine
Day 9 Kayak Lago & Río Grey, Transfer to Puerto Natales Puerto Natales
Day 10 Fly to Puerto Montt, Transfer to Puerto Varas Puerto Varas
Day 11 Trekking in Alerce Andino National Park Puerto Varas
Day 12 Day Trip to Isla Chiloé & Penguin Colony Puerto Varas
Day 13 Trekking to Osorno Volcano & Paso Desolación Puerto Varas
Day 14 Kayak La Poza Lagoon, Fly to Santiago, Depart  

Detailed Itinerary

Day 1: Arrive in Santiago, Afternoon City Tour

Enjoy the best views of Santiago from atop Cerro San Cristóbal

Welcome to Chile! In-the-know travelers agree that this is one of the best spots in South America to enjoy outdoor adventures. You'll venture deep into the famous Patagonia region soon enough—for now, the journey kicks off in Santiago, a grand metropolis nestled in a valley surrounded by towering Andes peaks.

A driver will pick you up at the airport and take you to the Singular Santiago, a 5-star luxury hotel in the capital's historic Lastarria neighborhood. After checking in, you can relax in your suite or enjoy a massage at the spa. Don't get too comfortable because soon you'll leave on a private city tour. Your English-speaking guide will take you to La Moneda, Chile's opulent presidential palace. Next up is Plaza de Armas, the main square. It's home to the 19th-century Palacio de la Real Audiencia (Palace of the Royal Court) and the Catedral Metropolitana, a neoclassical building that dates to 1753.

Other highlights include riding a gondola up to Cerro San Cristóbal, a hill that rises 984 feet (300 m) over the city. You'll also visit Mercado Central or Mercado La Vega—two municipal markets with vendors selling fresh seafood and produce. After the tour, you can grab dinner at one of the cool restaurants in Santiago's bohemian Bellavista neighborhood. Outside of Bellavista, you'll also find great eateries in the revitalized historic barrios of Yungay and Italia.

Day 2: Casablanca Valley Wine Tour

Venture into the Casablanca Valley to sample Chile's famous reds and whites

This morning, you're off on a full-day private wine tour around the Casablanca Valley. This famous viticulture region produces a wide array of varietals, including chardonnay, sauvignon blanc, pinot noir, and Chile's prized carménère—a bold, fruit-forward red. Your driver will pick you up for the one-hour transfer to the valley, which is strategically located near the Pacific coast. This area is ideal for growing grapes, with sea breezes and fertile soil providing perfect conditions for them to thrive. 

The first winery you'll stop at is Viña Casa Marín, a vineyard set on rolling hills above the tiny town of Lo Abarca, just a mile (1.6 km) from the ocean. Tour the grounds with a sommelier to learn about the production process and taste three varieties of their coveted wines. You'll also discover how Viña Casa Marín is famed for being one of Chile's first female-founded wineries. 

Continue on for a tour of the acclaimed Matetic Vineyards, where a guide will teach you about their biodynamic production techniques, followed by a tasting of their renowned organic wines. Soak up sweeping views of the valley as you wander the vineyards, then descend to the underground cellar for more tastings. At the end of the afternoon, you'll transfer back to Santiago.

Day 3: Fly to Punta Arenas, Historic Walking Tour

Look out over the Strait of Magellan at your historic boutique hotel (photo courtesy of La Yegua Loca)

It's a long journey this morning as you say goodbye to Santiago and hop a 3.5-hour flight deep into Patagonia and Punta Arenas. Founded in 1848 on the eastern shore of the Brunswick Peninsula, this colorful and historic city was once home to the crème de la crème of Patagonian society. Today, it's a tourist destination and hub for adventures in Torres del Paine.

In town, your driver will drop you off at La Yegua Loca (The Crazy Horse). This family-run boutique hotel lies in the city center, a five-minute walk to Cerro de la Cruz (a viewpoint overlooking the Strait of Magellan). The property is a beautifully restored home dating to 1929, with well-equipped theme rooms that evoke a time when Punta Arenas was a frontier outpost. You'll experience it at the restaurant, which serves regional classics based on recipes from the owners' immigrant grandparents, and when you sit down at the pulperia, a throwback to the general store/taverns of the early 20th century.

After settling in, you'll meet a local guide for a private, two-hour walking tour around town. Start with a stroll around the picturesque Plaza Muñoz Gamero, admiring its French street lamps, Magellan statue, and surrounding neoclassical mansions. Then, visit the 19th-century Palacio Sara Braun—a throwback to the time of wealthy sheep-ranching families—and continue to the revitalized waterfront area for a seaside walk. Lastly, venture to Mirador Cerro de la Cruz to enjoy perfect sunset views over the Strait of Magellan before indulging in a delicious seafood dinner at a local restaurant.

Day 4: Wildlife Boat Tour on the Strait of Magellan

Spot some of the unique wildlife species in this corner of the world, like the Peale's dolphin

Today's adventure will take you on a thrilling private excursion down the famed Strait of Magellan. But this is no leisurely cruise—you'll be zipping along strait in a Zodiac-style speedboat. It's a full-day tour celebrating the marine and wildlife of the region.

First, you'll journey to the San Isidro area in search of the beautiful Peale's dolphin. This species is native to the waters around southern Chile and is known for its unusual black and gray coloring. It's common to see pods of up to 12 adults swimming along the side of the boat and performing aquatic acrobatics. Also, keep an eye out for sea lion colonies, as well as various sea birds, such as albatross, petrels, and penguins. After a full day of traversing the strait, you'll return to Punta Arenas in the late afternoon.

Day 5: Transfer to Puerto Natales, Lago Sofia Horseback Ride

Enjoy premium views of the Última Esperanza Sound from your room (photo courtesy of Singular Patagonia)

Wake up early and meet your driver for the three-hour drive north to Puerto Natales. This small port city on the Seno Última Esperanza (Last Hope Sound) is famous as a base for adventures in Torres del Paine, the crown jewel of Chile's national parks. This legendary protected area covers 700 square miles (1,810 sq km) and is renowned for its circuit treks. 

Your driver will drop you off at the Singular Patagonia, another in the Singular portfolio of 5-star luxury hotels located worldwide. The Patagonia addition is located just north of the city on the waterfront. Set in a historic building from the industrial era, the Singular has been converted into a model of luxury, with each of its elegant rooms and suites offering views of the sound and mountains.

Plan your trip to Chile
Chat with a local specialist who can help organize your trip.

After dropping off your bags, meet another driver for the 30-minute ride farther north to Lago Sofia. There, you'll be greeted by your local gaúcho (cowboy) guide and meet your four-legged friend for today's horseback ride. Hop in the saddle and embark on a 2.5-hour excursion around this scenic area as you trot along the lagoon's shores. During the adventure, you'll pass through ancient forests, enjoy panoramic mountain views, and spot endemic wildlife, such as the magnificent Andean condor. After the ride, return to your hotel.

Day 6: Transfer to Torres del Paine, National Park Tour

Transfer to a family-run ranch within Torres del Paine National Park (photo courtesy of Hotel Las Torres Patagonia)

Rise and shine! This morning, you'll meet your private driver for the 1.5-hour transfer to Torres del Paine. Upon arrival, you'll check into Hotel Las Torres Patagonia, a 4-star lodge set against the backdrop of the iconic Paine massif. This family-run former ranch enjoys an ideal location at the start of the famous W Trek (the most popular circuit hike in the park) and is close to major landmarks like Lago Sarmiento. Highlights include dozens of well-appointed rooms, a spa and wellness center, and a restaurant serving gourmet dishes utilizing ingredients fresh from the on-site garden.

You'll have plenty of time to enjoy the hotel amenities later. For now, meet your private guide for an introduction to the splendor of Torres del Paine. You can choose from various routes, with each trail leading to spectacular viewpoints looking out to the park's lakes, glaciers, and granite peaks. Highlights you might visit include the Salto Grande waterfall and Lago Amarga, an alkaline lake whose shimmering waters reflect the gorgeous mountain scenery. As you hike, keep an eye out for local wildlife like Andean condors and guanacos (a relative of the llama).

Day 7: Self-Guided Day Hike to Las Torres Lookout

The spectacular view from Mirador Base Torres
There's no better selfie spot than the glacial lagoon at Mirador Base Torres

This morning, you'll embark on perhaps the most famous day hike in Torres del Paine: the 11.2-mile (18 km) trek up to Mirador Base Torres. This self-guided adventure begins with an ascent along a trail up Mount Almirante Nieto, which features stunning views of Lago Nordenskjöld and the Asencio Valley below. After two hours of hiking, you'll reach Refugio & Camping Chileno, where you'll break for lunch.

Then it's another hour of hiking past ancient lenga forests until you arrive at a moraine. The next part is a 45-minute hard scramble to the top and Base Torres. In this spot, three granite pillars jut out of the ground over a silver lagoon and make for the best view in the park. You'll also see the towering peaks of nearby Torre Sur, Torre Central, Torre Norte, Condor's Nest, and Glacier Torre. The trek ends when you hike back down the mountain.

Day 8: Self-Guided Lago Nordenskjöld Hike

Hike along the shores of Lago Nordenskjöld and marvel at its turquoise waters

There's no shortage of unspoiled glacial lakes in Torres del Paine, and today, you'll explore one of the best. You'll have the option of a half-day hike (6.8 mi/ 11 km) or a full-day trek (6.8 mi/ 22 km) around Lago Nordenskjöld.

This lake lies amid the dramatic landscapes of Torres del Paine, with the majestic peaks of the Paine massif (and the famous Horns of Paine) rising above its famous turquoise waters. Throughout the hike, you'll enjoy prime views of the area's peaks and glaciers as you travel through native forests and rock-hop over rushing rivers. At the end of the day, you'll return to your hotel. 

Day 9: Kayak Lago & Río Grey, Transfer to Puerto Natales

Paddle around the icebergs of Lago Grey on a kayak adventure

After breakfast, meet your private kayaking guide and take a short transfer to the shores of Lago Grey, another famous lake home to a magnificent glacier of the same name. After gearing up and brushing up on safety, you'll paddle to the southern end of the lake, arriving at an "iceberg graveyard" dotted with massive chunks of ice that have broken off the glacier. From there, enjoy spectacular views of the Paine massif and its western peaks, as well as the Horns of Paine.

From the lake, continue paddling into the mouth of the Río Grey. It then becomes a more adventurous trip as you kayak through river canyons and over rapids the rapids, rewarding you with awe-inspiring views of the Sierra del Toro peak. Upon reaching the Grey Bridge, stop for a picnic-style lunch, then continue to the confluence of the Río Serrano, where you'll disembark and meet a support vehicle for the transfer back to Puerto Natales and the Singular Patagonia.

Day 10: Fly to Puerto Montt, Transfer to Puerto Varas

Panoramic lake views from your 4-star Puerto Varas retreat (photo courtesy of Hotel Cabaña Del Lago)

Leave southern Patagonian behind as you board a two-hour flight north this morning to Puerto Montt. This port city is located in Chile's fertile Lake District (itself a gateway to Patagonia), where snowcapped volcanoes meet forested islands dotted with shimmering lakes. From Puerto Montt, meet your driver for the 30-minute ride north to Puerto Varas, which sits on the vast shores of Lago Llanquihue. Named "the City of Roses" after the flowers that line its streets, Puerto Varas offers a mix of German colonial architecture and Indigenous Mapuche culture.

You'll be staying in the north of town at Hotel Cabaña Del Lago, a 4-star retreat overlooking Lago Llanquihue. This stylish, contemporary hotel was designed so that its spacious rooms, suites, and eco-cabins offer expansive views of the lake and the snowcapped volcanoes beyond. Other treats at Cabaña del Lago include an indoor heated pool with a slide, wellness facilities like a spa and fitness center, and a collection of restaurants, grills, and bars, each offering lake views. 

Day 11: Trekking in Alerce Andino National Park

Explore another unspoiled corner of Chile's Lake District

It's another early start, as you'll leave this morning for the 30-minute transfer back to Puerto Montt. Then, it's another 30 minutes south to the coastal town of Lenca and the gateway to Alerce Andino National Park. Grab your water bottle and lace up your hiking boots because when you arrive at the trailhead, you'll set off on a privately-guided hike.

The route you'll follow runs along the edge of the Río Chaicas. The scenery in this part of the Lake District is nothing short of spectacular as you'll pass through great swathes of temperate forests of arrayán and alerce trees. You'll also stop at Lagos Chaiquenes and Triangulo—two glassy mountain lagoons that happen to be great spots for birding—keep an eye out for austral parakeets, woodpeckers, and the Andean condor. At the end of the trek, you'll return to Puerto Varas.

Day 12: Explore Isla Chiloé & Puñihuil Penguins National Reserve

Tour Isla Chilóe, known for its colorful towns and scenic beauty

In the morning, you'll transfer to Puerto Montt, then continue up the Panamericana 5 Highway to the port of Pargua. Here, you'll set off on a 30-minute boat ride across the Chacao Channel to Isla Chiloé. This striking archipelago showcases dense forests, rolling green hills, and caves steeped in legends. Stop in the town of Ancud to visit its museum and market, then soak up the view from Cerro Huaihuen, which features landmarks like Fuerte San Antonio, an early 19th-century Spanish fort that played a significant role in the wars for independence.

Next, head to the Caulín Bird Sanctuary, a haven for over 60 migratory bird species that gather off its pebbly beach, including black-necked swans, flamingoes, and herons. The bird theme continues with a trip to a penguin colony in nearby Puñihuil, the only place in the world where Magellanic and Humboldt species coexist. In the late afternoon, return to Puerto Varas and treat yourself to a relaxing evening in town.

Day 13: Trekking to Osorno Volcano & Paso Desolación

Today, you'll ascend the slopes of the iconic Osorno volcano

For your penultimate day in Chile, embark on one more epic hike. After an early breakfast, join your private guide and hit the road out of Puerto Varas, skirting Lago Llanquihue as you head toward the iconic cone shape of Osorno for a trekking adventure through the Andes. Along the way, pass the mouth of the Río Pescado (Fish River), plus the villages of La Poza and Los Riscos. You'll begin your hike once you reach the volcano's base at around 2,000 feet (600 m).

The six-hour hike, which covers around 7.5 miles (12 km), circumvents the volcano along the Paso Desolación (Desolation Path), named for the windswept slopes covered in lichens and shrubs that afford you stellar views during the trek. After circumventing the volcano, which sits at over 8,000 feet (2,600 m) high, take the path down to Lago Todos Los Santos. There, you'll enjoy spectacular views of the Tronador and Puntiagudo volcanoes, the snow-covered summits of the Andes, and the lake's emerald waters. Return to Puerto Varas at the end of the afternoon.

Day 14: Kayak La Poza Lagoon, Fly to Santiago, Depart

Once more into the great Patagonian outdoors

It's your final day in Chile—though there's just enough time to sneak in one last excursion. Meet your private kayaking guide in the morning and transfer to Laguna La Poza, a small lagoon connected to Lago Llanquihue by a skinny channel. Weeping willows and volcano views abound in this hidden gem, and you'll spend the morning paddling through the hanging willow tunnels, bird-watching, and enjoying total peace and tranquility before reality beckons you home.

Later, return through the channel to Lago Llanquihue and disembark. A driver will be waiting to transfer you back to the airport in Puerto Montt, where you'll catch a flight to Santiago and your onward connection. Safe travels!

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Map of Luxury Adventure in Chilean Patagonia - 14 Days
Map of Luxury Adventure in Chilean Patagonia - 14 Days