Blog
7 min read

This Backcountry Day Almost Ended Badly...

Written by
Derek Cirillo
Published on
October 7, 2026

So we spend a lot of our winters hiking in the backcountry. And honestly, as I get older, I’ve realized I don’t care about ripping 20 runs anymore.

Give me 3 or 4 good ones.

Take my time. Walk through the woods. Talk with friends. Eat some onigiri at the top. Then drop into untouched powder all the way down… rinse and repeat, I’m back by 2 o’clock, I can work drink a Latte.

That’s the good stuff.

And when you enjoy something that much, of course you want to share it with your friends.

Nick and I, my partner at YukiHomes, we’re out there all winter. We even train a little in the offseason too, mainly zone 2 runs, just to be ready for the winter. I compete in Jiu-Jitsu, he’s super active… so for us, this is normal.

But then our buddy comes to Japan.

We’ll call him G Money… because I’m not trying to embarrass him.

We kept telling him:
“Come on, you’ve gotta try this.”
“It’s easy.”
“It’s beautiful.”
“You’re gonna love it.”

Now to be fair, G can ride. Snowboarded his whole life. Surf’s well. We knew he’d be fine on the way down.

What we underestimated… was the way up.

So we finally convince him.

It was a perfect day. Bluebird. Like 30 degrees (sorry for all you Celsius readers out there). One of the most beautiful hikes I’ve ever done. Just untouched, glistening snow as far as you can see with the contrast of a bright blue sky.

And before anyone freaks out, we did it right.

We had a full pack for him and hired a guide just to be safe. Avalanche risk was low that day.

Everything checked out. But man… the uphill destroyed him.

Falling over, sliding backwards, just getting absolutely worked within the first 15 minutes of the uphill.

At first it was funny, first time skinning, everyone goes through it. Nothing to be concerned about.

But what was supposed to be a 2–3 hour tour…

Turned into a 7-hour survival mission.

We barely made it back before needing headlamps.

If our boy G moved any slower, he would’ve been standing still. Not to mention his binding snapped so we had to use a ski strap to lock his foot in on the downhill.

At that point, his legs were fried, so why not pile on some gear failures too?

It stopped being funny some point around hour 4.

He was completely gassed, severely dehydrated, Just wrecked. By the end, our guide basically had to carry him out. And I swear… we thought G was gonna kiss the guide on the lips in the parking lot.

They hugged, went forehead to forehead and I think one of them puckered up, I wont say who…

So we take him to a local hospital. Get him on an IV drip and get him feeling better.

And while healthcare is Japan is universal, from my understanding the national health insurance system covers 70% and residents pay the remaining 30%, it is not free for tourists.

Your responsible for 100% of medical costs, often paid upfront at the hospital. While prices are generally lower than in the U.S., even minor treatment can add up quick.

We partnered with SafetyWing a while back, so we’ve been using their travel insurance for some time now.

Did G really need to go get an IV? Probably not, some electrolytes from the konbini might’ve been enough. But we had the insurance and figured, let’s just play it safe, get him feeling better quicker, and make sure he could enjoy the rest of his trip.

And honestly, it was well worth it, he bounced back.

And this was something minor.

We’re out there for months. Deep in the backcountry. Every single day where things go wrong.

And after that trip… I will never travel without insurance again.

It’s cheap. It’s a no-brainer.

This isn’t a 7-day vacation anymore. When you’re spending months in one place, the odds of something happening go up, even something as simple as catching a bad virus.

Put it this way: would you live for 2 months in your home country without health insurance?

I wouldn’t…

So if you’re one of our clients spending extended time at your place, or someone who travels for long stretches, get the insurance. Don’t think twice.

SafetyWing Travel Insurance

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This content is for informational and educational purposes only and reflects my personal opinions and experience. I am not a licensed financial advisor, tax advisor, or attorney. Readers should conduct their own due diligence and consult qualified professionals before making any investment decisions.

Derek Cirillo
September 28, 2026

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Our team

Meet the founders.

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Derek Cirillo
Co-founder

Derek has been working in the Airbnb space for the past 10+ years and recently purchased a home in Japan. He is excited to bring this investment opportunity to others in the States & abroad.

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Nick McLoota
Co-founder

Nick has a passion for adventure and has always dreamed of owning a property in Japan. His dreams finally came true when Derek brought him in on a deal of a lifetime in Hokkaido, Japan - one of Nick's favorite places on Earth.