Perhaps you’re starting to put away your heavy sweaters and scarves, but before you do, you should know the snow is starting to dust the high peaks off to the east of Santiago — a truly idyllic winter scene. Chile is a wonderful place to visit in winter!
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Handpicked for this season
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Valparaiso
From: $275.00 USD p.p.
Discover the hidden beauty of this unique harbor town in Chile called Valparaiso. Admire the beautiful murals, street artists, historical sites, & delicious seafood. Enjoy a boat ride in the harbour or visit the museum house of Pablo Neruda!
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Self Drive Tour
From: $1,500.00 USD p.p.
We have set out the most amazing self drive tour in the South of Chile for you! We start in Puerto Montt and end in Temuco.
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Colchagua Wine & Dine
From: $1,190.00 USD p.p.
Colchagua 4 Day Wine & Dine Tour: the ideal trip for a romantic getaway or the perfect excuse to treat yourself to a weekend of fine cuisine & relaxation!
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Tour Types
Blog
Experience the Real Chile: A Journey Off the Beaten Path
Travelling should be more than just checking off a list of places—it’s about uncovering moments that stick with you. If you’ve ever been let down by cookie-cutter tours or crowded tourist traps, you’re not alone. Many travelers are searching for something more authentic, something that feels real.
At Chile Off Track, we’ve made it our mission to offer just that: genuine, local experiences that take you to the heart of Chile. Whether it’s riding horseback with Arrieros (local cowboys) through the Andes, tasting wines with boutique winemakers, or stargazing under some of the clearest skies in the world, we give you a chance to dive into Chile in a way most people never will.
Tired of Feeling Like Just Another Tourist?
Picture this—you’re excited to finally see a new place, but once you get there, you’re caught in a sea of tourists. The tours feel rushed, the experiences feel scripted, and it’s easy to wonder if you’re truly connecting with the culture at all. If this sounds familiar, it might be because traditional travel doesn’t always dig deep enough. It leaves you wanting more—more connection, more authenticity, and more moments that make your trip feel personal.
That’s exactly why we do things differently.
Finding real connections in Chile
Recently, we worked with a family of six who didn’t want the typical vacation. They wanted something more, something that felt tailor-made for them. So, we put together a custom road trip that took them through some of Chile’s most beautiful, hidden regions. It kicked off in the Casablanca Valley, where they met boutique winemakers and got a taste of vintages that never make it outside of Chile. This wasn’t just a wine tour—it was an intimate look at the craft and the passion behind every bottle.
Next, they headed up into the Andes to ride with local arrieros (local cowboys). These aren’t your average tour guides; these are people who know the land inside and out, sharing their stories, knowledge, and love for the rugged beauty of the region. Finally, the family spent a night under the stars with one of our local astronomers, learning about the constellations in one of the best stargazing spots in the world. By the time their trip ended, they didn’t just feel like they had visited Chile—they felt like they truly experienced it.
Why This Matters to You
These kinds of experiences don’t happen by chance. They come from working with locals who are as passionate about their craft as they are about sharing it with you. At Chile Off Track, we partner exclusively with local arrieros, astronomers, and winemakers—people who live and breathe Chile. Plus, all our guides speak both Spanish and English, so you’re never left out of the conversation.
Is it Time for Something Different?
If you’ve ever felt like travel should be more than just seeing the sights, now’s your chance to experience something deeper. Whether it’s riding through the Andes, discovering boutique wines, or spending a night under the stars, we’re here to make it happen.
At Chile Off Track, we believe travel should be personal, immersive, and above all, authentic. We’re all about creating experiences that forge real connections with the land, the people, and the culture.
Ready to Plan Your Adventure?
Let us help you plan the trip of a lifetime. Get in touch with us today to book your personalized tour and experience the real Chile—off the beaten track.
Fiestas Patrias in Chile
Fiestas Patrias: The colorful traditions in Chile on the 18th of September burst out alive to celebrate their independence from the Spanish Conquistadores. Are you ready for some tasty asado while watching the cueca dance? The 18th of September or the “Dieciocho” is, without a doubt, the most popular and most celebrated national holiday of Chile!
Chilean Rodeo
Chilean Rodeo has a history reaching back over 400 years but was not recognized as a national sport until 1962 by the Chilean Olympic Committee (Comité Olímpico Chileno). Chilean rodeo’s history begins somewhere between the years of 1557 and 1561 when the first “huasos” (Chilean cowboys & horse riders) began going up into the Andes to herd the season’s new calves back to the city to be branded and sorted.
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