Thirty Days in Thailand: A Live Travel Diary

Tuesday, Oct 28 – Travel Day 1
Location: Halifax → Toronto
Mood: Jet-lagged gremlin with a sinus infection brewing

Welcome to the chaos.

This isn’t a guide. It’s a play-by-play of a month in Thailand — equal parts chaos, curry, and very likely some questionable decisions.

I’m writing this live, daily, as we go without filters or edits or “perfect” travel influencer stuff (we’ll do all of that later) because I thought it would be fun to do something a little messy.  You see a shit-ton of overly curated, AI-generated, and embellished content online so I want to do something entirely different this month.

And, I write in a travel journal anyway, so I thought I’d let you read over my shoulder and see what’s really going on.

This is me — writing what actually happens over the next 30 days as we make our way to, and around, Thailand. The good, the bad, and the “why is this happening to me” stuff.

If you’re here for perfect photos and polished travel tips, you might not like it here (and that’s OK).

If you’re here for the real, messy, funny, honest version — pull up a chair.

There will be complaining (it’s a diary, after all)

There will be swearing

There will be unhinged, unfiltered thoughts

But there will also be insights about what really happens when we spend a month travelling around a country we’ve never been to.

Here’s how this will work:

• When I travel, I keep detailed notes in a journal or diary — that part stays the same
• Every morning, I’ll share those notes with you (along with the unpolished photos that never make the highlight reel) right here on the blog.
• You can take it or leave it!  Check back daily for live updates.

Day 1 – The Uber Ride from Hell

Last week was a blur in the best way possible. We spent seven days at Devour! — eating, filming, and surviving on caffeine while shooting for a client. It was incredible: brunching with Ali Hassan, tasting Canada’s top chefs’ creations, and hanging out in the green room with Dwayne Dopsie (aka the Jimi Hendrix of accordion). But we are wrecked.

We got home Sunday night around 8 p.m., had one day to get our shit together, do laundry, repack, and try to make our apartment look less like a bomb went off before heading to the airport at 6 a.m. this morning.

And, naturally, I woke up with a nasty cold. Sore throat, congestion — the full “please-don’t-let-this-turn-into-something-worse” package.

We always Uber to the airport (way cheaper than parking for a month), but this morning’s driver was… unhinged. Missed the exit, drifted into the shoulder (multiple times), hit those rumble strips that scream “you’re about to die,” sped up to 130 km/h, then slammed back to 90. I was clutching the holy-shit-handle like a life raft and praying to whoever non-religious people pray to that we’d make it in one piece. Spoiler: we did.  But honestly, I was pissed.  That guy shouldn’t be driving — ever.

Airport was smooth. Security was smooth thanks to the upgraded baggage scanners (side note: why did this take so long).  It seems archaic that we’ve been unloading our bags, pulling out liquids, taking out laptops, and all the other security bullshit we’ve had to do for all this time, no?

Grabbed eggs benny (as one does) in the airport, boarded zone 2 thanks to credit card perks which means never worrying about space for your bags, and — since we travel carry-on only — zero baggage stress. Because life’s too short for baggage claims.

Then came my favourite part of air travel: seat recliners. Let’s call this Airplane Pet Peeve #1:  I get it, the seats move. But jamming your chair into someone’s knees for three hours? Rude. I was actually fantasizing about sneezing right on his head, but I resisted the urge.  Also, is this your first day flying sir?  You f***ing know you can’t recline the seats until we’re in the air, but there are always an extraordinary number of people who do it anyway.

Airplane Pet Peeve #2: people who rush the aisle before it’s their turn. You know the ones. No.  Sit your ass down.  “Excuse me, ma’am, that’s not how this works.” I’m the person who mutters it loud enough to make eye contact.

Anyway — I sound like a complainer, but I’m actually so damn excited for this trip. We landed in Toronto, scored early check-in at the Sheraton (11 a.m., thank you Bonvoy status), and I did a little NSDR protocol while Brent went for a beer.

Now I’m wrapping up a few client projects, setting my OOO reply, and making sure our coordinator’s ready to handle Mills & Co. while we’re gone.

My mom and stepdad fly in tonight, and tomorrow’s a chill Toronto day before we head west to Vancouver (Trip Lag 2).

Thirty days. One cold. Questionable Uber drivers. Let’s go.

Photo of the Day:

If you have questions or commentary, I’d love to have a dialogue with you on this series.  It’s truly meant to be relatable, real and raw.  I don’t know about you, but I’m sick of the clearly glossy, over-edited travel content that’s flooding the internet.  I want to see the messy middle, so that’s what this is!

We’ll also be sharing our daily play-by-play (in real time, which is rare for us) over on Instagram, so join us there as well and follow along.  Click here to visit us on Instagram