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Once upon a time in Chile—What’s in a CEO’s bucket list?

20 odd days. No itinerary. No common language. One country. Adventure of a lifetime.

And that’s how our very own Co-Founder Srinath Shankar fulfilled his bucket list journey.

If you were a travel hacker with enough insider knowledge to plan a trip to any part of the world, where would you go? “It should be Chile”, said Srinath in a lunchtime conversation. “No itinerary, no much prior planning, and perfectly fine if it means missing a few things”, said he as he went on about why there’s nothing like this South American gem. Not only did he visit his dream destination soon after, but also found that Chile is everything he expected it to be, and more.

In those 20 dreamy days, he stayed in the middle of the surreal Patagonias, witnessed a real-life money heist, carried 70-75 kg gear throughout a 5-day trek, and moved with people who never speak English. Here’s what Srinath has to say about his dream vacation.

Chile is quite far to go all the way just for it. Weren’t you tempted to include more countries in your itinerary?

Chile as a whole, including its dramatic Patagonia mountains, the deserts and the marble caves, was in my bucket list for so long. Of course, it was tempting to visit Argentina, Bolivia, and Peru but it was a conscious call that I and my friends took — to take our time and explore the magnificent country that Chile itself is. It’s for the same reason that we are going all the way to Chile, we didn’t want to cram many things at once without exploring anything in-depth at all. In fact, if you look closer, Chile is very vast lengthwise and moving across varied terrains and seasons is no mean feat. So yes, we spent 20 days in exploring Chile alone, and we don’t regret it one bit.

Where did you go in Chile?

Chile is one of the driest places on earth and hence unusually remote. We could see it in the Atacama, the world’s driest desert. The remoteness itself was attractive and tourist crowd was almost non-existent. Our next plan was Carretera Austral or Route 7 stretching from Puerto Montt to Villa O’Higgins — the most scenic route in Chile to drive around. All the more, most of Chile hasn’t seen the light of mass tourism, and it felt like it was just us and the mountains.

Can you share an interesting instance from your trip, where something turned out to be completely different from what you had expected?

There was one experience though, which completely caught us off guard. We are not new to trekking and the 5-day trek with no high-altitude climbs (maximum 1000m) sounded like a piece of cake at first. What we totally underestimated was that we have to carry 70-75 kg worth tents, travel equipment, sleeping bags, stove, food and water all by ourselves. It was overwhelming at first, but manageable as we went ahead. I broke my water bottle though and had to rely on the infrequent water bodies for the rest of the trek.

You said you didn’t plan much. Did it work, or is there anything you’d plan differently if you go again?

I would make visa arrangements for neighbouring countries for any sudden plans. We wanted to visit Bolivia badly when we learnt that it was just 300 km away from the Atacama desert. And what better way than by driving? But unfortunately, visa on arrival is applicable only if you transit through the airport. You need a regular visa to enter the country by road. Unaware of this, we drove all the way to the border only to hear this and come back. Happens, especially if you plan an impromptu trip. Nonetheless, the drive from the Atacama desert to the Bolivia border was gratifying to the core.

Did you discover anything new about Chile that you didn’t know before? A quirky fact, perhaps?

Their love for dogs and reverence for tourists no matter what, he says.

Almost every home in Chile has a dog, partly due to the scattered human population and partly because everyone has a farm and they need a guard pet. Well-trained and smart, the adorable Chilean dogs were very friendly even with strangers.

Tourists were completely safe even amidst an ongoing protest! Chilean protest was going on at a massive scale at the time we visited. Although we couldn’t see the impact in remote places, Santiago made us realize the scale of it. It looked like a real-life version of Money Heist! Protesters were large in number and we realized it’s nothing new when we saw rebellious graffitis painted on every wall there is. But to our much surprise, no one was harmed in any way and they were very respectful of tourists. We watched everything live, a protest heavily inspired by Money Heist. Though a nation-wide protest, there were no sudden bursts of outrage or vandalisation of properties. An organized, controlled protest if you will.

What insider tip will you give for people visiting Chile in the future?

You will find it difficult to manage with English. Learning Spanish will go a long way — at least so you can manage without feeling lost. Almost no one here, including the airlines and whatnot, will speak/understand English nor will they make an effort to. Good for us, we learnt how to say “no carne (meat), no pollo (chicken), and no pez (fish)” not long after 🙂

In short, there’s nothing about Chile that doesn’t “make the cut”. You can go without a plan and still come back having enjoyed the trip of a lifetime. We started with a vague idea of how many days to spend where—5 days in the desert, 5 in the mountains, 5 on the road, and so on. We didn’t feel held back anywhere nor did we feel pressurized to follow the clock. We went with the flow and that was the best decision about this dream trip.


Sometimes it’s best to put ourselves out there and let serendipity do all the work. So glad it worked for our boss. Now, where will you go, if you can choose any place in the world?

Akshaya Devi

Scared of driving in Chennai traffic but also planning a solo bike trip to Ladakh. Don't be surprised if you find me all hyper, someone somewhere in the world must've misquoted Martin Scorcese or justified a bad coffee saying "C'mon, coffee is coffee".