Dreaming of an unforgettable journey through Argentina and Chile? That’s exactly what Sally and Paul had in mind when they reached out to us. But they weren’t looking for just any trip—They wanted to taste, connect, and truly experience South America authentically—with all the richness and intimacy it has to offer.
When Sally and Paul first reached out to us, they had a simple but heartfelt request: to craft a journey across Argentina and Chile that blended cultural depth, natural beauty, and—most importantly—culinary delight.
“We’d love something that’s rich in food, wine, and local stories”
They said during our very first video call, their eyes lighting up with anticipation.
They weren’t interested in rushing through tourist checklists. They wanted time. Time to savor a glass of Chardonnay at sunset, to chat with the locals over dinner, to explore at their own pace—knowing someone had thoughtfully arranged every detail behind the scenes.
In that first call, we knew we were a match.
And so began the journey of designing a custom Argentina and Chile itinerary just for them—one that unfolded slowly, soulfully, and with deep intention.
In Episode 8 of our podcast Stories Across South America, Sally and Paul reflect on that journey. They speak candidly about what it meant to work with a small, women-owned travel company like ours. They share stories of warmth, of connection, of drivers and guides who became friends, and meals that became moments of joy.
If you’re wondering how to craft an itinerary to Argentina and Chile that goes beyond the ordinary, you’re in the right place.
In this blog post, you’ll find their complete story, travel tips, and a day-by-day look at their adventure.
Here’s a little about us—and why travelers like Sally and Paul choose to explore South America with us when they’re looking for a Chile and Argentina itinerary that’s truly personal.
🌎 We’re a women-led, boutique family company and passionate local experts with more than 20 years of experience designing once-in-a-lifetime journeys in South America. For us, every trip is handcrafted with thoughtful detail, always tailored to the spirit and interests of our travelers. No two journeys are ever alike. Each one becomes a story—a celebration of culture, food, nature, and the joy of slow, intentional discovery.
Planning a trip to Argentina and Chile? Get our Free Luxury travel guide. Curated by us, Clara and Maria. Get more Itinerary ideas for your trip!
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How to plan your Argentina and Chile itinerary?
Planning your Argentina and Chile itinerary begins with one key question: What do you truly want to experience? Whether it’s sipping wine in Mendoza, Exploring the Glaciers in Patagonia, or savoring a private dinner in a Buenos Aires home—you can shape your journey around what moves you.
Argentina and Chile are vast and diverse. Trying to see everything in one trip is neither realistic nor rewarding. Instead, focus on depth over breadth.
Think about how much time you have (10 days? 2 weeks?) and choose 3 to 4 regions that complement one another in pace and personality.
For Sally and Paul, it was a culinary and cultural itinerary across Chile and Argentina that included:
- A mix of city life, countryside, and coast
- Intimate experiences with locals
- A relaxed pace that gave them space to explore—and to rest
Our advice? Work with someone who listens. Someone who can help you plan a trip that’s logistically seamless and emotionally rich. And be honest about what matters most to you: food, history, nature, ease, authenticity.
That’s how a great itinerary begins.
Now, let’s dive into Sally and Paul’s Argentina and Chile Itinerary
From our podcast Stories Across South America | Ep. 8: Argentina and Chile: A Dream Journey with Paul and Sally
Watch the full Episode on YouTube here 👇
Best Places to Visit for your Argentina and Chile itinerary
Paul and Sally’s route included many of the most beautiful places in South America: – Santiago de Chile with its vibrant neighborhoods and the iconic Plaza de Armas. – Casablanca Valley, a dream for wine lovers. – The coastal town of Zapallar, perfect for some quiet luxury. – The magical Lake District on both sides of the Andes: from Puerto Varas and Puerto Montt in Chile to Bariloche in Argentina. – Finally, Buenos Aires, the Paris of South America, alive with tango, architecture, and incredible food.
READ MORE: Famous Landmarks to See in Argentina
When is the best time to visit Argentina and Chile?
One important thing to consider when planning your Argentina and Chile itinerary is the climate. Since both countries lie primarily in the Southern Hemisphere’s temperate zone, the seasons are opposite to those in the U.S. and Europe. That means summer runs from December to February, and winter from June to August.
Argentina and Chile are wonderful destinations if you’re looking to escape northern winters. While there’s a small tropical area in the far north, most of both countries experience a mix of cool, dry weather in the south (like Patagonia) and warmer, more humid conditions in the central regions.
There’s truly no “bad” time to visit—but certain times offer specific advantages depending on what you’re after.
👉 High season (late spring through summer, November to February) is ideal for exploring Patagonia, the Lake District, and the Andes. Weather is warm and outdoor adventures abound. But keep in mind: January is peak summer, and beach towns and popular cities can become crowded and expensive.
👉 Early autumn (March–April) and early spring (September–October) are personal favorites. These seasons offer mild temperatures, fewer crowds, and great value. Paul and Sally traveled in April—and it was glorious. Vineyards were golden, the weather crisp and pleasant, and the destinations peaceful without the summer rush. It’s a time that lets you slow down and truly enjoy the landscapes, the food, and the people.
👉 Winter (June–August) is colder, especially in Patagonia, but can be a great time for snow activities or visiting the north, like Salta or the Atacama Desert, where conditions are still comfortable.
If you’re not fond of humidity and big crowds, it’s wise to avoid Iguazu Falls in summer or national holidays like Easter and Carnival, when prices and bookings peak.
Ultimately, the best time to visit depends on what you want to experience—but for cultural travel, food, wine, and relaxed discovery, early spring and fall are unbeatable.
That’s why April was the perfect choice for Sally and Paul.
As they shared in our podcast, they weren’t looking for summer heat or big crowds—they wanted to soak in the ambiance of small towns, sip wine in peaceful vineyards, and explore nature at a slower pace. April gave them all that and more: mild temperatures, golden autumn colors, and the chance to engage with locals in a more intimate way. Their Argentina and Chile itinerary unfolded with ease and elegance, one meaningful experience at a time.
READ MORE: Patagonia in December: Argentina and Chile Suggested Trips
Experiences You Can’t Miss
There are moments in a trip that go beyond the itinerary—that linger in the senses long after the flight home.
For Sally and Paul, it started with a morning stroll through Santiago’s local markets, where the air was thick with spices and laughter, and ended in a private kitchen, learning to prepare a traditional Chilean meal alongside a warm-hearted host. It was more than a cooking class—it was connection over food, flavors, and stories.
They still talk about their time at Matetic Vineyard. Nestled in the Casablanca Valley, the biodynamic tour wasn’t just about wine; it was about rhythm—of the land, of the seasons, of care. Surrounded by vines and golden hills, they tasted, they paused, they felt fully present.
Crossing the Andes by boat? Yes, it’s real—and it’s spectacular. The Lake Crossing from Puerto Varas to Bariloche is a full-day journey of emerald waters, forested trails, and the kind of beauty that makes you sit in silence. It’s not something you do; it’s something you experience.
One of their favorite days came next: a scenic drive along the Seven Lakes Route, stopping for a gourmet picnic by a quiet Patagonian river. They lingered in nature’s quiet grandeur, sipping Argentine Malbec and savoring local cheeses as condors soared above.
In the coastal town of Zapallar, they wandered along cliffs with the sea crashing below, ate fresh seafood in sleepy cafés, and let time slow down. And in Buenos Aires? The magic wasn’t in the tango shows or big city lights—but in the closed-door dinners, the shared laughter with locals over homemade empanadas, the feeling of being welcomed like old friends.
These weren’t just activities. They were moments of presence, taste, and heartfelt discovery—the kind of experiences you simply can’t miss.
The People You Will Meet Along the Way
An itinerary through Argentina and Chile is never just about which destinations you choose, or how you connect the dots with flights and transfers. What truly shapes a journey—and transforms it into something unforgettable—is the people you meet along the way. The human connections are what turn a beautiful place into a meaningful memory. These encounters are often the moments that stay with you long after you’ve unpacked your bags.
For Sally and Paul, this truth came alive each day of their trip. Their guides weren’t just knowledgeable—they were heartfelt, thoughtful, and genuinely invested in sharing their world. “They felt like family,” they said. Pablo, their driver, became such a trusted and kind presence that they specifically asked for him again and again. With each journey, he didn’t just navigate roads—he opened windows into the daily life and values of his community.
In Santiago, Carolina welcomed them into her home with warmth and generosity, sharing not just a meal, but her story, her culture, and a heartfelt hospitality that moved them deeply. These moments of intimacy and shared humanity were the soul of the trip.
And there was us—the team behind the scenes, always just a message away. “We’d send a message and see the three dots… They were always on it,” Paul said. That constant, caring support wasn’t about logistics alone. It was about presence. About knowing you’re in good hands, even when you’re miles from home. This is what it means to travel thoughtfully, and with people who care about more than the itinerary. We’re here not only to plan the trip, but to walk it—quietly and attentively—alongside you.
Paul and Sally’s Argentina and Chile Itinerary
Itinerary Highlights
Paul and Sally spent 13 unforgettable days traveling across Chile and Argentina—a journey carefully designed with their love of food, culture, and human connection at its core. Looking back, they talk about the highlights that made their trip truly special.
One of their favorite experiences was the day they wandered through the bustling local markets of Santiago before joining a private cooking class in a local home. There, they didn’t just learn recipes—they shared stories, laughter, and flavors that would linger with them long after they left.
In Casablanca Valley, they were surrounded by vines and golden hills during a wine tasting that wasn’t just about sipping—it was about learning, slowing down, and feeling the rhythm of the land. Their time at Matetic Vineyard, with its biodynamic philosophy and exquisite pairings, was a moment of peaceful indulgence.
Zapallar offered a different kind of luxury: quiet walks by the ocean, fresh seafood under the sun, and the simple joy of having nowhere to be except fully present.
The lake crossing from Chile to Argentina was, as they described it, “like a meditation through nature.” This full-day journey by boat and road took them through glassy lakes and forested trails, with the Andes as their silent witnesses.
And then there was the gourmet day tour of the Seven Lakes, where they picnicked by a riverbank in Patagonia, sipping Malbec and savoring hand-prepared bites with the snow-dusted mountains as their backdrop.
They closed their journey in Buenos Aires, a city that wrapped them in its charm. But what they loved most wasn’t the typical sights—it was the cultural immersion. From private dinners in local homes to wandering the streets of Palermo, it was the spirit of the city and its people that stayed with them.
Quick Look: Paul & Sally’s 13-Day Argentina and Chile Itinerary
- Day 1: Arrival in Santiago – Welcome meeting and rest.
- Day 2: Flavors of Chile – Cooking class and local food tour in Santiago.
- Day 3: Into the Vineyards – Wine tasting in Casablanca Valley, overnight at Matetic Vineyard.
- Day 4: Wine & Wellness – Biodynamic wine experience and outdoor excursion.
- Day 5: Coastal Escape – Scenic drive to Zapallar, seaside relaxation.
- Day 6: Seaside Serenity – Free day in Zapallar: cliff walk, seafood, ocean views.
- Day 7: Journey South – Flight to Puerto Montt, transfer to Puerto Varas.
- Day 8: Across the Andes – Lake Crossing to Bariloche.
- Day 9: Patagonian Picnic – Seven Lakes gourmet tour and riverside lunch.
- Day 10: Capital Connection – Flight to Buenos Aires, explore San Telmo.
- Day 11: Slow Buenos Aires – Free day and dinner with locals.
- Day 12: City Farewell – Art, parks, and a final night in the capital.
- Day 13: Departure – A heartfelt goodbye to South America.
Day-by-Day Detailed Itinerary
Day 1 – Arrival in Santiago de Chile – A Warm Welcome to South America
Paul and Sally landed in Santiago in the early afternoon and were greeted with a private transfer to their charming boutique hotel, Magnolia. Nestled in the heart of the city, just a few blocks from the Plaza de Armas, the hotel blended heritage architecture with modern elegance. After settling in, they enjoyed a welcome meeting with our expert local guide, who introduced them to the rhythm and spirit of Santiago. The rest of the day was left open for rest and light exploration.
Day 2 – Culinary Immersion in Santiago – Flavors and Stories in the Capital
Their first full day was dedicated to the senses. After breakfast, they visited a bustling local market with their guide, exploring fresh ingredients, tasting seasonal produce, and absorbing the local atmosphere.
By midday, they arrived at a private residence for a hands-on cooking class. Sally learned to mix the perfect pisco sour—her new favorite—while Paul discovered a passion for Chilean stews. They ended the afternoon gathered around a communal table, enjoying what they’d created with wine pairings and rich conversation.
Their first full day was dedicated to the senses. After breakfast, they visited a bustling local market with their guide, exploring fresh ingredients, tasting seasonal produce, and absorbing the local atmosphere. By midday, they arrived at a private residence for a hands-on cooking class. Sally learned to mix the perfect pisco sour—her new favorite—while Paul discovered a passion for Chilean stews. They ended the afternoon gathered around a communal table, enjoying what they’d created with wine pairings and rich conversation.
Day 5 – Coastal Beauty in Zapallar -By the Pacific’s Edge
A scenic private transfer brought Paul and Sally to Zapallar, a picturesque coastal town beloved by Chileans seeking tranquility. Their hotel, Isla Seca, offered sweeping ocean views and a relaxing atmosphere.
The rest of the day was theirs to wander, soak in the sea breeze, and enjoy a slow seafood dinner overlooking the waves.
Leaving Santiago behind, the couple journeyed through the rolling vineyards of the Casablanca Valley. Their first stop was Veramonte Winery, where they were treated to a private tour and guided tasting. They then continued to Casas del Bosque for a gourmet lunch and more wine in an idyllic setting. By late afternoon, they arrived at the serene Matetic Vineyard, where they were welcomed with a signature cocktail and a slow-paced dinner at the Equilibrio Restaurant—an evening defined by elegance and earthy flavors.
Day 4 – Wine, Nature, and Tranquility at Matetic – Wine, Nature & Balance
This day was all about slowing down. After a biodynamic tour of the vineyard—learning about the natural rhythms and practices that shape Matetic’s wine—they enjoyed a five-course tasting menu, paired with premium Corralillo and EQ wines.
In the afternoon, they chose a gentle biking tour through Rosario Valley. The scenery, the stillness, and the golden light of late summer made it a deeply memorable day. Another cozy dinner followed, paired once again with wines that now carried new meaning.
This day was all about slowing down. After a biodynamic tour of the vineyard—learning about the natural rhythms and practices that shape Matetic’s wine—they enjoyed a five-course tasting menu, paired with premium Corralillo and EQ wines. In the afternoon, they chose a gentle biking tour through Rosario Valley. The scenery, the stillness, and the golden light of late summer made it a deeply memorable day. Another cozy dinner followed, paired once again with wines that now carried new meaning.
Day 5 – Coastal Beauty in Zapallar -By the Pacific’s Edge
A scenic private transfer brought Paul and Sally to Zapallar, a picturesque coastal town beloved by Chileans seeking tranquility. Their hotel, Isla Seca, offered sweeping ocean views and a relaxing atmosphere. The rest of the day was theirs to wander, soak in the sea breeze, and enjoy a slow seafood dinner overlooking the waves.
Day 6 – Free Day in Zapallar – Seaside Serenity
This was a day of unhurried pleasure. They took a short hike up Cerro de la Cruz for panoramic coastal views, strolled along quiet beaches, and visited local galleries. Lunch was fresh ceviche and local wine in a quaint restaurant. It was a day of open time, where moments unfolded naturally and joyfully.
Day 7 – From Zapallar to the Lake District – From Coast to Lakes
In the morning, they journeyed back to Santiago and caught a domestic flight to Puerto Montt. From there, a private transfer took them to Puerto Varas, where they checked into a cozy boutique guesthouse. Dinner was quiet and relaxed—homemade, hearty, and full of anticipation for what came next.
Day 8 – Crossing the Andes – A Journey Through Mountains and Water
This was the day Paul and Sally would never forget. The Lake Crossing from Chile to Argentina is a rare gem in travel: a combination of buses and boats that wind through volcanoes, turquoise lakes, and national parks. From Petrohué to Peulla, Puerto Frías to Puerto Blest, each leg revealed new wonders. The final arrival in Bariloche, just as the sun began to set, felt magical. They checked into their hotel with tired smiles and full hearts.
Day 9 – Gourmet Adventure Along the Seven Lakes -A Patagonian Feast for the Senses
Their private guide picked them up for a full-day tour through the famed Seven Lakes Route. They visited the charming village of Villa La Angostura, stopped for scenic photos, and finally enjoyed a gourmet picnic by the Pichi Traful River, accompanied by Argentine Malbec. In the afternoon, they visited San Martín de los Andes and took a short walk along Lake Lácar before returning to Bariloche.
Day 10 – Flight to Buenos Aires – Touchdown in the Capital
After a relaxed breakfast and lakeside farewell, they transferred to the airport and flew to Buenos Aires. Their welcome meeting with our local team set the tone for the final days. Their Airbnb apartment in San Telmo was perfect: warm, local, and full of personality. They ended the evening with dinner in a tucked-away parrilla where the steak melted in their mouths.
Day 11 – Exploring Buenos Aires -Wandering and Wonder in the City
With no schedule and all the freedom, Paul and Sally wandered through Palermo’s leafy streets, discovered hidden cafés, and browsed bookstores. They even joined a short tango class in the late afternoon—clumsy but laughing. That evening, they were welcomed into a local home for a closed-door dinner, sharing stories and wine with porteños as if they’d known each other forever.
Day 12 – A Day to Savor the City – Art, Roses & Reflections
Their final full day was about absorbing the city at their own pace. They visited MALBA (Museum of Latin American Art), shopped in Recoleta, and took a slow walk through the rose gardens of Palermo. That night, they returned to one of their favorite restaurants from earlier in the trip, savoring a last toast to their unforgettable journey.
Day 13 – Departure Title: Until Next Time
A private transfer brought them to the airport. Though their bags were heavier with gifts and wine, it was the memories—the stories, the people, the rhythm of each place—that they carried home with them
Listen to the full Episode and learn from Sally and Paul about their Chile and Argentina Itinerary
Listen and Watch on Spotify here 👇
Where to Stay on Your Argentina and Chile Trip
Sally and Paul’s journey through Argentina and Chile was deeply enriched by the boutique accommodations selected for them—each chosen not for luxury, but for charm, character, and authenticity.
These weren’t grand resorts, but rather unique stays that felt personal and welcoming.
In Santiago, they stayed at Hotel Magnolia, a beautifully restored building in the heart of the city with thoughtful design touches.
At Matetic Vineyard, their room overlooked rolling vineyards, allowing them to immerse themselves in the region’s wine culture. Hotel Isla Seca in Zapallar provided serene ocean views and a cozy atmosphere perfect for slow coastal days. In Puerto Varas, they found warmth and hospitality at Mero Gaucho, a boutique inn where they were welcomed like family.
Their Patagonian chapter took them to Design Suites Bariloche, offering sweeping lake views and Patagonian flair. These carefully chosen accommodations helped turn each destination into a memorable chapter of their journey.
👉Read More: 31 Best Resorts in Argentina (Our boutique and luxury list!)
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How Far in Advance Should You Start Planning Your Argentina and Chile Itinerary?
Argentina and Chile may still feel like hidden gems to many travelers—but that’s part of their charm. The flip side? The most memorable experiences—those charming boutique hotels, passionate local guides, and once-in-a-lifetime routes like the lake crossing from Puerto Varas to Bariloche—are limited in number and high in demand.
That’s why it’s essential to start planning your trip several months in advance, especially if you’re traveling between November and March, which is peak season in the Southern Hemisphere. If you’re celebrating something special—like a honeymoon, retirement, or milestone birthday—even more reason to plan ahead.
Early booking allows you to secure the best accommodations, benefit from flight deals, and take advantage of early bird offers many hotels and boutique experiences provide.
With pristine landscapes in remote corners, character-filled stays, and a wealth of food and wine, Argentina and Chile are two of South America’s most captivating destinations. Between them, you’ll find it all: lush jungles, the awe-inspiring Iguazu Falls, ancient glaciers, the windswept end of the world in Tierra del Fuego, tranquil lakes, world-class wine regions, and deeply rooted cultural traditions—tango, gaucho life, fútbol, fine dining, art, and more.
As we always say, choosing what to include in your itinerary can be a challenge—because there’s so much to love. But as Sally and Paul discovered, this isn’t just one trip. It’s the beginning of a love story with South America. And for many of our travelers, one visit turns into many.
For over 20 years, we’ve helped curious travelers from around the world design custom-made journeys across South America. What we offer isn’t just logistics—it’s heart, care, and local expertise.
When you travel with us, you’ll receive:
✔️ Handpicked, boutique accommodations with real character
✔️ Meaningful experiences curated to your passions
✔️ A fully personalized, worry-free itinerary
✔️ Thoughtful support before and throughout your journey
Want to start planning your own journey through Argentina and Chile—but not sure where to begin?
👉 Book a consultation call with us. Let’s talk about your travel dreams and begin shaping your one-of-a-kind itinerary.
With warmth,
Clara ❤️
PS: What’s calling you most—wine, glaciers, tango, or the Andes? Tell us over on Instagram. We’d love to hear from you.
More Great SOUTH AMERICA Itineraries
Looking for more inspiration for your trip to SOUTH AMERICA? Check out these other Argentina in 10 days itineraries and Patagonia 10 days itineraries, explore different ways to spend 10 days in Argentina and Chile. Check out our suggested itineraries for South America.
✨ Ask Across — Real Q&A from Women Who Get It
How long do you need in Argentina and Chile?
we recommend a minimum of 12 to 14 days. This gives you enough time to explore a few key regions—like Santiago, the Casablanca Valley, Patagonia’s Lake District, and Buenos Aires—without feeling rushed. If you have 3 weeks or more, even better—you can add destinations like the Atacama Desert, the glaciers of El Calafate, or the vibrant north of Argentina. But no matter how long you stay, the real magic lies in slowing down, connecting with the people, and savoring each place with intention. Sally and Paul’s 13-day journey is proof that with thoughtful planning, even two weeks can become the trip of a lifetime.
Can you do Chile and Argentina together?
Absolutely—you can (and should!) do Chile and Argentina together. In fact, they’re a perfect pair for a well-rounded South American adventure.
Thanks to their shared border and complementary landscapes, you can seamlessly combine Chile’s coastal charm, wine valleys, and dramatic Andes crossings with Argentina’s vibrant cities, lake regions, and rich cultural heritage. Many of our travelers, like Sally and Paul, choose to begin in Santiago, wind through Casablanca Valley, cross into Argentina via the stunning Lake District, and finish in Buenos Aires—all in one thoughtfully paced itinerary.
With good flight connections, scenic overland routes, and expert local support, a custom Chile and Argentina itinerary is not only possible—it’s one of the most rewarding ways to experience South America.
Is Patagonia better in Chile or Argentina?
The truth is, both sides are extraordinary, but offer very different experiences.
Argentine Patagonia is famous for its wide-open landscapes, stunning glaciers, and charming towns like El Calafate and El Chaltén. Here, you can hike to Laguna de los Tres, marvel at the Perito Moreno Glacier, or drive scenic routes around the Lake District. It’s ideal if you love variety—wines, wilderness, and warm local culture.
Chilean Patagonia, especially around Torres del Paine National Park, is more remote and wild, with dramatic granite peaks, turquoise lakes, and some of the most iconic trekking routes in the world. It’s perfect for travelers seeking raw nature and immersive hikes in pristine surroundings.
If you can, combine both sides—they complement each other beautifully. One offers soul-stirring hikes and silence; the other, a mix of nature, tradition, and vibrant small towns. As with Sally and Paul’s journey, it’s the contrast that often makes the experience unforgettable.
How easy is it to travel between Chile and Argentina?
Traveling between Chile and Argentina is easier than you might think—especially with the right planning.
The two countries share one of the longest land borders in the world, with multiple crossing points by air, road, or even boat. Many of these routes are not just functional—they’re spectacular. For example, Sally and Paul crossed from Puerto Varas (Chile) to Bariloche (Argentina) via the famous Lake Crossing, a seamless journey through a series of lakes and Andean mountain passes. It’s part transportation, part once-in-a-lifetime scenic experience.
You can also fly between major cities like Santiago and Buenos Aires in under 2 hours, or use private transfers and direct buses for shorter overland crossings like Mendoza–Santiago or El Calafate–Torres del Paine
While border formalities exist, they are straightforward, and with local support and private drivers, the transitions can feel smooth and stress-free. With thoughtful pacing and expert logistics, traveling between Chile and Argentina becomes part of the adventure—not a hassle.
If you are ready to book your trip- Book your consultation video call with us. It all starts there. We will get to know you to design a TRUE custom trip for you.
