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Want to ski at 3,300 metres in Chile? You need more than bravado to make it.Ski Portillo

Sometimes things don't go as planned – and those moments often make for the best stories. Tripping columns offer readers a chance to share their wild adventures from the road.

I was never supposed to ski on that August winter's day, which explains why I showed up at one of South America's greatest ski hills wearing jeans, running shoes and a thin jacket. I was at Portillo, an exclusive resort with championship-grade slopes situated deep in Chile's interior, right near the Argentinian border.

It sits in a high Andean Mountain pass, and the runs actually cross the main east-west highway.

I was heading up the switchback highway (29 hairpins in all) just to see it, and from the car I could see people gliding down long, fresh carpets of snow. I watched with bright eyes as they skied right over the highway, using avalanche sheds as bridges, and shushed back and forth to the bottom far below. I knew I had to do it, too.

My tour guide tried to warn me off (she'd clearly seen this kind of thing once or twice before). But I would not be deterred. Quickly assembling a rag-tag outfit (borrowed ski pants and hastily arranged equipment, including gloves from what must have been the lost and found), I skied out to lift, whose towers and swinging chairs arched up and out of sight, over a craggy ridge.

Once I was on the lift, I knew I was in trouble. It turns out that I'm not built to ski at over 3,300 metres. I felt dizzy, started seeing tiny translucent stars and was breathing heavily after little exertion. I rationalized that it was just some initial jitters, nothing to worry about. But as I swooshed down the pristine slopes and into the kilometre-long run – the one that crosses the highway – altitude sickness hit me hard. My legs cramped and began shaking as I made my cuts, back and forth. I started to feel nauseous. I took frequent "breaks," my name for a controlled collapse on the mountainside, where I would lay for 10 minutes, my chest heaving, sweat soaking through my shirt.

Needless to say, I was a bit worried. Only one other skier passed me when I was taking a "break." He conscientiously came over to make sure I was okay. I wasn't, really, but my foolish pride shooed him away, with assurances that I was just a little tired and would be on my way soon. A few minutes later I heard a helicopter and wondered if he'd alerted some sort of elite unit of the Chilean ski patrol.

He hadn't, and I made it to the bottom – eventually. I took a long and indulgent break on a little bench before boarding the lift again. It spirited me back over the highway where I made eye contact with an Argentinian trucker. I offered a weary wave, and he, hair slicked back and eyes hidden behind reflective shades, offered a thumbs-up and a toot of his horn. I took it as a sort of congratulations, putting a wan smile on my face as I headed back over the ridge and toward the warmth and safety of the lodge, with nothing more strenuous than a hot toddy in my near future.

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