Day 6 – When The Shit Hits the Fan

Day 6 – When The Shit Hits the Fan | Chile Travel Diary

Date: Tuesday, March 24
Location: Viña la Playa → Hacienda El Huique → Santa Cruz
Distance: 38.5 km / 24 miles
Mood: Frustrated, exhausted, barely holding it together

When the Highlight Reel Breaks

If you travel enough, eventually shit hits the proverbial fan.

Let me tell you about the last 24 hours.

First — when you’re on a work trip like this, it’s not what people think. Everyone else is here to enjoy the scenery, make memories, soak in the experience. And we do too — we really do — because this is a pretty fucking cool job. But that’s not why we’re here. We show up on these trips with a set of “deliverables”, shot lists, and expectations. There’s always this underlying pressure (lots of it self-imposed, but not all) and very real. We have a client relying on us to capture everything, and that doesn’t just happen.

It’s one thing when you’re somewhere on your own with full control of your time. When Airbnb or resorts bring us in, we typcially have a minimum of 3 nights in one place to account for variables like weather and other conditions. It’s quite another thing when you’re on a group tour with a tight schedule, fixed timelines, weather variables, and other guests.

You’re constantly doing the math:

Do we have time?
Is the light right?
Can we get the shot without disrupting anyone?
Where do we charge everything?
Do we have time to eat?

And then something small shifts — like a longer lunch stop — and suddenly that window you were counting on is gone. Case in point: we stayed at one of the most iconic properties on this trip, and we had exactly one night there. We checked in at 4:45 pm, had a wine tour at 5:30, dinner at 7:30… and it rained.

No drone.

So we planned to get up early the next morning before checkout at 8:30. Breakfast was at 7:30, the sun doesn’t come up until 8 (you get the point). And…Heavy fog. Lowest ceiling they’ve seen there.

As I mentioned yesterday, we flew the drone anyway, but the shots weren’t what people expect. I actually think they’re beautiful — moody, grey, a little mysterious — but that’s not what performs. People want blue skies and sunshine. And just like that, the opportunity was gone. No redo.

We left feeling like we failed. Even though there was absolutely nothing we could have done differently.

The Shot We Got (and What It Cost Us)

After leaving Vik with that feeling sitting in our chests, the weather finally cleared, and we pushed ahead of the group and found this incredible stretch of road — trees lining both sides, arching overhead like a tunnel. It looked almost too perfect, like someone had designed it that way.

We got the drone up.

First me, riding back and forth — over and over — to get the shot. Which sounds simple until you realize every extra pass adds to your distance, your fatigue, your energy for the rest of the day. Then the group came through and we got it! The shot. And then…well, if you read yesterday’s entry, you know what happened.

And then the wind took the drone and slammed it into a tree. One of the arms broke. And just like that, everything shifted because drones don’t fly when they’re broken. And this was day two of riding. Not good. This is what we’re here to do and now our equipment is broken.

Huge credit to Brent here — because while I spiralled a little internally, he went straight into problem-solving mode. Found epoxy (thanks to Jata), figured out a temporary fix, and got it to a place where we might be able to limp through the rest of the trip. Not ideal. But better than nothing.

When It Piles On

This morning, we got up early again — new vineyard, new opportunity — and we slammed a quick breakfast down to get back on the bike and capture more content before the group departure at 9 am.

That added another 45 minutes of riding to my day before we even officially started. The shots were good. Not perfect, but good enough. And sometimes, that’s all you get.

Then we started the ride to Santa Cruz, which was about 40km of really beautiful riding, but somewhere along a rough stretch (which is ironic because the roads are generally in great shape), Brent’s phone fell off his bike. And got run over by a car (or truck). Completely fucked.

No phone = no GPS. So now we’re relying on other riders for navigation, which we both hate — but Brent especially. He’s wildly independent, and having to rely on someone else throws him completely off. It also meant we had to ride at someone else’s pace, stop when they stopped, go when they went.

It sounds small, but when everything else is already off, it’s the kind of thing that pushes you right to the edge. This was very close to Brent’s breaking point. And when that happens (which is rare) — not intentionally, but inevitably — we start taking it out on each other.

We know it. We try not to. But when things stack up like this, everything starts to feel heavier than it should.

The “Quick Stop” That Wasn’t

When we got into Santa Cruz, what we really needed was downtime. Instead, we spent the afternoon walking for hours trying to find someone who could fix the phone. What we thought was a quick 2-minute walk turned into an hour.

I was in flip flops. And a dress. That turned into a massive blister on the bottom of my foot and some chafing that was… not ideal. You get it.

We finally found a shop way off the beaten path (in a residential area) that a local had told us about (trying to help) — and while we appreciated the effort, it felt a little questionable — and they told us they couldn’t fix it the same day. We were prepared to leave a $2000 phone there, with a stranger, overnight, with no guarantee or any kind.

So we walked all the way back. And then, finally found another place that could help. Shoutout to the sweet Chilean people who are more than willing to patiently wait for us to muddle through Google Translate, trying to explain what we need.

$400 later, Brent has a semi-working phone.

Front camera is gone, which means no biometrics, which means remembering passwords like it’s 2008 again — but at least the data is intact. And honestly, at that point, that felt like a win.

Meanwhile… Real Life Is Still Happening

All of this is happening while:

I’m still sick
My breathing is mediocre at best (great for cycling 2–4 hours a day)
Neither of us is sleeping
And we both forgot to sunscreen our hands, so now we have aggressively sunburned hands

It’s just… one of those days.

But Also… Not Everything Was Bad

Because it wasn’t all bad.

We rode through some of the most beautiful landscapes we’ve seen so far.

We stopped at Hacienda El Huique, which felt like stepping into another time — a preserved colonial estate with so much character. I met the sweetest orange cat who completely monopolized my attention (as they do), and there was a massive magnolia tree that genuinely took my breath away.

We found Gli Aranci in Santa Cruz — a little sandwich shop that made unreal Cubanos — and we did what we always do: ordered different things and split them. Half for lunch, half for dinner.

We sat in the bar at Hotel Santa Cruz Plaza with a beer and actually talked. Reset. Got back on the same page.

For context, our relationship is strong — like, really strong. Not in a braggy way, but in a way that comes from doing the work. We’ve spent years building communication, self-awareness, and a level of honesty that means we’re usually very aligned, very respectful of each other, and genuinely each other’s biggest fans.

So when we have a day like this — when things go sideways, and we start to feel it in how we show up with each other — it feels noticeably off. The flip side of that is we also know how to come back from it, quickly. And sitting there, with a beer, after everything that had stacked up over the last 24 hours, we did exactly that.

A Small Reset (and a Much-Needed Win)

We’re here for two nights, which means no packing in the morning. That alone feels like a luxury right now. And then — the guides surprised us with bottles of wine from Viña Casa Silva. The winery we toured… without tasting.

Brent got a red, I got a white. Such a small thing, but it felt like a really thoughtful gesture at exactly the right time.

Final Thoughts

This probably reads like a bit of a “woe is me” entry, and that’s not the intention.

But I do think it’s important to share this side of travel too because social media is fake. What you usually see is someone’s highlight reel. They don’t show the messy middle or when things go wrong. But this?

This is real life. Sometimes things go sideways. Sometimes a lot of things go sideways all at once. And you still keep going.

We’re ending the day grateful, a little exhausted, and cautiously optimistic that maybe… just maybe… we’re due for some good luck. Might even buy a lottery ticket tomorrow.

Food Breakdown 🍽️

Winner of the Day: Cubano sandwiches from Gli Aranci
Close Second: Beer at the hotel bar (earned)
Drink of the Day: Whatever that cold beer was — it hit perfectly

Photo of the Day

📸 Honestly? Probably none. But let’s go with the moody Hotel Vik photos, shall we?

Hotel Vik, Chile

Hotel Vik (on a rare foggy day)

✈️ Travel Tip of the Day

If everything starts going wrong at once, lower your expectations and just solve the next problem. Honestly, I really believe we have a lot more control over our experiences than we think, and it’s primarily your attitude. Look, after these last 24 hours, I’m the first to admit that our attitudes needed some heavy adjusting, but we once read, “the universe only gives you what you can handle”. So here we are, handling it. And very thankful we have each other.

Let’s Talk About It

Do you think people share enough of the “real” side of travel — or just the highlight reel? Do you like hearing this side? Or do you prefer the glossy version?