Day 1 – The Trip We Almost Didn’t Take | Chile Travel Diary

Date: March 18 → 19
Location: Halifax → Santiago
Mood: Smug, shockingly well-rested, slightly feral about airplane etiquette

Before we get into it, a quick note on what this is…

If you were here for the Thailand series, you already know the vibe. If you’re new — welcome to the chaos.  This is a live travel journal (more like a diary). No polish, no perfectly curated highlight reel, no “top 10 things to do” energy. Just real-time thoughts, reactions, opinions, and the messy middle of what travel actually looks like while we’re in it.

When I did this in Thailand, I honestly didn’t think anyone would care. Turns out…a lot of you did. So we’re doing it again — this time from Chile.

Same rules apply: I write what actually happens. The good, the frustrating, the funny, and the “what the hell is going on” moments.

You can take it or leave it — but if you’re here for the real version of travel, you’re in the right place.

Opening Spiral

We weren’t supposed to be here.

This year was supposed to be the “let’s chill out and not hemorrhage money on travel” year. We’ve always valued experiences over things (it’s one of the things we aligned on so early on in our relationship), and although our business is growing rapidly again, which means we can afford to travel, that growth also requires us to be boots on the ground, supporting our team.

Also, we’re not budget travellers — I would call us mid-tier.  That means, we still fly economy (but regularly use points or e-upgrades to get into business when we can), we don’t mind spending money on amazing food and experiences, and we like to stay in nice places (think 4 stars or better) — boutiques & Airbnbs when we can, and Marriott properties the rest of the time (because, points).  So our travel takes some moola…hence the “let’s take it easy this year” goal.

We even said no to Italy and the South of France with my Dad, step-mom, aunt, and uncle. Which…still feels illegal to say out loud.

But here’s the thing — if I’m doing the South of France and spending that kind of money, I want vineyard patios, warm air, everything in bloom, swimming in the Mediterranean Sea, rosé in hand, living my best life. March is not that. March is “this could have been better if you waited.”

So we made the logical choice.
We declined.

And then Chile showed up. Same dates. Completely different direction.

Tell me the universe doesn’t intervene sometimes.

I’m a little “woo” — I’ll own that — but this felt like one of those moments where you’re about to make a good decision, and then something better quietly slides into place.

Had we said yes to France, we would have missed this. Our first time in South America. A completely new continent. A work opportunity that actually excites us.

That would have sucked.

So yeah…this one feels aligned.

The Flight (AKA: I Finally Acted Like a Person With a Plan)

I need to document this because it’s a breakthrough.

I slept on the plane. Properly. Nearly six hours.  That does not happen to me.  I’ve been travelling since I was 9 years old; frequently for the last 12 years, and after the insane Thailand jet lag we experienced, I vowed to do every single thing in my power to not repeat that trauma.  Transparently, I don’t sleep well in general either, so expecting a restful sleep at 30,000 feet seemed like a pipe dream.  But…

This was an 11-hour flight from Toronto, and instead of just raw-dogging it like I usually do (hope for the best, wake up miserable), I treated it like a system:

• 10K steps + full heavy lift workout before the flight

• 3L of water + electrolytes

• 10mg of melatonin as soon as we boarded

• Noise-cancelling headphones with brown noise (loud enough to drown out everything else)

• Eye mask + TRTL (turtle) pillow

And it worked (which is why I don’t give a single f*ck what I looked like (as evidenced here):

Quick note on the noise thing, because this actually matters:

• White noise = all frequencies at equal intensity (kind of harsh, static-like)

• Pink noise = softer, more balanced, closer to natural sounds like rain

• Brown noise = deeper, lower frequency, more like a rumble — think distant thunder or a plane engine hum (very fitting, I thought).

Brown noise is the least aggressive and, for me, the easiest to fall asleep to. It feels grounding instead of irritating.

Between that, the fact that we were exhausted from flight delays of 3 hours (we finally boarded at 1:30 am) and the melatonin, I was out before they disconnected the bridge and I stayed out…for nearly 7 hours.

Woke up feeling like a human instead of a travel goblin.  Look, I know this was a “first try” so it’s not a valid test yet, but I will repeat this pattern moving forward so I can report back with some harder data!

Pet Peeves of the Day (Because Of Course There Are)

Let’s set the scene.

We are flying from Halifax to Toronto to Santiago. Same timezone (from Halifax – it’s 1 hour difference from Toronto, still inconsequential).

It was an overnight flight. But at some point…night ends. Morning happens. The sun is fully up.

And yet — at 11:30 a.m. — we are still sitting in a pitch-dark cabin with all the windows tinted.  Why?  If anything, shouldn’t you be helping people adjust to the actual time of day they’re landing into?

Instead, we’re all sitting in this artificial nighttime bubble while the sun is aggressively existing outside.  Maybe there’s a policy. Maybe I’m missing something. But from where I’m sitting, it feels like no one wants to deal with the transition, so we’re just…not doing it.

They eventually turned the lights on, but it felt late (it was almost noon). Like we were all being gently gaslit into thinking it was still 3 a.m.

Also — while we’re here:

Airplane Pet Peeve #2: TAKE YOUR SHOES OFF? STRAIGHT TO JAIL.

I’m sorry. No. Absolutely not.

Shoes off. Socks off. Bare feet on the floor where everyone else is putting their bags, their blankets, their lives?  It’s disgusting. It’s disrespectful. It should be illegal (like death penalty illegal).

And while we’re talking about feet — if you are getting on an 11-hour flight without compression socks, I need you to reconsider your life choices immediately.  This isn’t just comfort — it’s circulation. Blood clots are a real thing on long-haul flights.  Ask your friendly neighbourhood pharmacist!

I had mine on. Zero swelling.

The girl in front of me? Ankles spilling over her sneakers by the end of the flight. I’ve been there. It’s painful, and it’s avoidable.

Wear the damn socks!

This Trip Is Different (In a Way That Still Feels Slightly Surreal)

This isn’t just a “go explore and eat everything” trip.

We’re here for work — but in the best possible way.

We’re marketing strategists. We run our own agency. We work with travel brands to build and execute full marketing strategies — everything from positioning to content to guest experience.

This particular client runs cycling and adventure tours in 11 countries around the world, and this one is their Chile wine and bike experience.

So yes — this is work.

But it’s also:

• Experiencing the tour as guests

• Capturing content in real time

• Observing what works (and what doesn’t)

• Helping refine the experience from the inside

It’s one of those “this is a real job?” moments.

We arrived two days early to settle in before the tour starts, which already feels like the best decision we’ve made.

Travel Reality Check: The Carry-On Debate

We did carry-on only. As always.  Except…we had to check one bag for the client.  And I hated every second of it (if you’re reading this, we were happy to do it 😜).  

But when we’re travelling for ourselves, we don’t check bags. Ever.

And it never fails, every single trip, someone says, “I could never do carry-on only.”

Sir, you could. You just don’t want to.  Let’s just call it what it is.  If you’re happy waiting for and lugging around suitcases, you do you, Boo.  That’s great.  It’s just not for me.

And here’s the thing:

It’s not every time you check a bag that something goes wrong…
but if you travel enough, it’s going to happen.

Lost. Delayed. Damaged.

Airlines mishandle millions of bags every year. It’s not rare — it’s just a matter of when.  And without fail, it’s always the people who are adamant that carry-on isn’t possible who end up:

• Waiting forever at baggage claim

• Filing a claim for lost or damaged luggage

• Stressing about where their stuff is

• Fighting their way up and down cobblestone streets with bags that weigh 100 lbs with broken wheels (an exaggeration?  Maybe.  But I’m not interested.

And maybe it makes me an asshole, but I always think:

“See, this is exactly why I don’t do this.”

First Glimpse of Chile (Yes, I Cried)

As we were descending into Santiago, the Andes came into view and I immediately teared up.  It’s a brand new mountain range for me, and it’s spectacular.

Not dramatically. Just quietly sitting there, looking out the window, completely overwhelmed.

I’ve been told my whole life by all kinds of people that I “oversell things.” That I get too excited. That I make everything sound bigger than it is.  And maybe that’s annoying to people but honestly, I don’t care.

I love that about myself.

I love that I can still be that affected by a place I’ve never been. That I can look at mountains and feel something.

The world is incredible, and we’re fed so much garbage by news, media, unethical influencers & celebrities that I actively choose to block that out and saturate my brain with things that I find awe-inspiring. I’m not toning that down for anyone, and I hope to never ever lose that part of myself.

First Impressions: The Arrival Energy

We grabbed one of the blue taxis right outside baggage claim — exactly where we were told they’d be. Super easy. Super organized.  It cost about $30 USD (~$40 CAD), compared to the hotel shuttle at $45 USD (~$60 CAD).  Really grateful that fellow travellers told us about the “blue taxis”.  We were also warned that there are a lot of unregistered car services that you should be aware of, so while we’re usually Uber users, we opted out this time (Uber actually isn’t legal here in Chile, although still common).

And then — the drive.

This is one of my favourite parts of travel.  That first look at a new place. The unfamiliar buildings, the pace, and the feeling that you don’t quite understand where you are yet.  There’s something about that moment that never gets old.

Hotel Bidasoa (And the Kind of Arrival You Actually Want)

We checked into Hotel Bidasoa and immediately knew we made the right call by booking here (it’s also the first stop on our official tour that starts on Saturday).

Boutique. Thoughtful. Beautiful.

It’s known for being one of the most sustainable hotels in Latin America, but what stood out right away was the service.  In hospitality, I put service above all else.  In my opinion, it’s more important that the food, the rooms, the location and even the atmosphere.  As someone who stays in close to (sometimes more than) 100 accommodations each year, and eats in hundreds of restaurants annually, I’ll die on that hill.  Service first, always.

We were offered a welcome drink — any drink.  Not the usual sugary pre-mixed situation or non-alcoholic bubbly some resorts do. Anything.

So we started with Carménère, obviously.

Chile produces about 96% of the world’s Carménère (originally from Bordeaux, rediscovered here in the ‘90s), and it’s been a favourite of mine for years — deep, rich, slightly spicy.

We also asked (last minute) to stay in the same room across multiple bookings, and they accommodated instantly.

That kind of thing matters more than people think.

Food, Wine & Not Rushing Anything

We kept the first night simple.

Wine on the terrace, a serrano ham board, and a simple Mediterranean pizza.  But the best part is not feeling rushed.  We have two full days here before the tour starts. No pressure to immediately go out and “see everything.” No frantic checklist.

We’ll wander.
Handle a bit of work.
Drink good wine.
Ease into it.

And honestly, that might be the biggest luxury of this trip.

Because once the tour starts, we know it’s going to be full — experiences, movement, and structure.

But right now, we get to just…arrive.

Reflection

One of the guiding principles we live by is that “every yes is supported by 1,000 no’s”.  That means that every time you say yes to something, you’re making a choice that will limit you elsewhere.  It’s meant to remind us to maintain our boundaries and say yes really thoughtfully – only to things we really want to do (which is hard for me because I have a genetic disposition to FOMO…thanks Mom).

We said no to one version of this year.  And that opened us up to being able to say yes to this.

And now we’re here — in a place we hadn’t even planned to be, at the start of something that already feels different.

If Day 1 is any indication, this is going to be a mix of:

• Work and adventure

• Structure and spontaneity

• Gratitude and appreciation

And honestly? That’s exactly how I like it.

Photo of the Day

📸 The Andes from the plane — the exact moment I stopped pretending I wasn’t emotional about being here

✈️ Travel Tip of the Day

If you want real sleep on a long-haul flight, treat it like a system — not a gamble.

Let’s Talk About It

Have you ever said no to one trip and ended up somewhere completely unexpected (and better)?