💸 Get compensated when travel goes wrong

Estimated read time: 5 minutes and 2 seconds

Good morning from Addis Ababa, Ethiopia, where I’m attempting to sleep on some bug-infested chairs during my 9-hour layover. 🪳

Now that I’ve made you feel a little better about your own current setting, let’s talk travel:

• 💸 How to get compensated when travel goes wrong

• 🏨 30% transfer bonus to a unique program

• 🙌 My international travel essential

💸 How to get compensated when travel goes wrong

Travel is magical, life-changing, soul-expanding… and occasionally an absolute dumpster fire.

And here’s the thing you should understand:

It is completely normal (and completely okay) to ask for compensation when the experience doesn’t match what you paid for.

And if you’re flying reputable airlines or staying in big hotel chains, compensation usually comes in the form of points — because that’s the system they already use for service recovery.

I’ve had a few examples of this recently, so let me tell you how I’ve navigated it:

1. Cathay Pacific business class

Last year, I flew Cathay Pacific business class from Hong Kong to Jakarta – a flight I booked for 32,000 Asia Miles.

I picked my usual window seat, because I’m a simple man with simple cabin-side personalities.

Cathay, however, said “what if… aisle?” and reassigned me at the gate.

Was it the end of the world? No.
Was it the seat I booked and paid miles for? Also no.

So I filed a short note through their online customer relations form. Nothing dramatic. Just the facts.

To my complete shock, Cathay credited 18,000 Asia Miles for the inconvenience – more than half the cost of the entire flight.

The point isn’t the number…. Though that is a very good number.

The point is: Airlines fully expect to give compensation when something isn’t right, especially in premium cabins.

You just have to tell them. 😌

2. Four Points by Sheraton: A comedy of errors

Cut to a very different vibe: the Four Points by Sheraton in Kigali, where I just spent three nights last week.

Everything – and I mean everything – was chaotic:

• They somehow thought I booked five rooms (I booked one)

• The electricity in my room kept dying (not the hotel, just my room)

• The hot water didn’t work

• They canceled my booking mid-stay and checked me out accidentally

• Staff repeatedly apologized throughout my stay

But here’s the interesting part:

They proactively offered me 15,000 Marriott points at checkout. I didn’t even ask… but if I had left without resolution, I would have absolutely asked.

Loyalty programs embed compensation guidelines into their playbook – and staff are trained to use points as a goodwill fix when things go wrong.

3. Sofitel Cotonou: A perfect stay… almost

Now for one that wasn’t funny at all.

At the Sofitel Cotonou in Benin – an otherwise phenomenal luxury hotel – one failure overshadowed everything:

They didn’t arrange the pre-booked cross-border transportation I’d confirmed with them twice, weeks in advance.

So I ended up traveling alone on one of the most dangerous roads in West Africa – corrupt police checkpoints, legitimate kidnapping risk, armed bandits, the whole ensemble – because the hotel didn’t deliver a very basic, safety-critical service.

I wasn’t looking for compensation. I genuinely just needed them to understand how serious it was.

The guest relations manager was mortified and took it incredibly seriously.

And a couple of days later, she texted me on WhatsApp, asking how she could make it right.

My reply? “Points.”

Next thing I knew, she promised me 30,000 Accor points in compensation.

Accor points have a flat fixed value of €0.02 each… so this compensation is worth a flat $700 USD, which is no joke – and commensurate with how they let me down.

The compensation playbook

Here is a quick guide for what to do and how to approach these situations to ensure you’re fairly compensated when things don’t go according to plan.

1. Always document everything

This means photos, receipts, screenshots, names of staff you spoke with, confirmation emails — everything.

2. Always be respectful

Most frontline staff aren’t the ones who caused your issue.

A calm, factual message gets you compensation infinitely faster than screaming at someone in a polyester vest.

3. Use official customer relations channels

In almost every case, a website form or a corporate email works better than trying to get something from the front desk.

Here’s why:

• They have discretion

• They can issue compensation directly

• You can get a case number to follow up on

So here’s the bottom line: You don’t need to accept bad travel experiences.

You can advocate for yourself (respectfully) and come out with something genuinely valuable.

And honestly? Sometimes the points almost soften the blow.

(Almost.)

🏨 30% transfer bonus to a unique program

One program we often forget about is Preferred Hotels and its I Prefer loyalty program.

It flies under the radar (for good reason), but actually has some fantastic use cases….

… especially when there’s a 30% transfer bonus, like the current one from Capital One miles.

The normal transfer ratio to Preferred Hotels is 1:2, which is already pretty cool. With this bonus, you’re looking at 1:2.6.

That means transferring 1,000 Capital One miles will yield 2,600 I Prefer points.

So what does this mean in practice?

Let’s look at the Oceans Edge Resort & Marina in Key West, which goes for 50,000 I Prefer points per night – that’s less than 20,000 Capital One miles for a beachfront stay.

If you want to get saucy with it, here’s another fun example:

Last year, I was in Ulaanbaatar, Mongolia. I remember driving by the Blue Sky Hotel and locals telling me it was the best hotel in the country.

Turns out, it's a Preferred Hotels property – and you can book it for just 11,500 Capital One miles per night with this transfer bonus.

Pretty cool, huh?

Now here’s the big caveat… ThankYou points also transfer to Preferred Hotels… but at a 1:4 ratio.

So if you have both Capital One miles AND ThankYou points, you’ll definitely want to use the latter for Preferred Hotels.

If you recently signed up for the big welcome offer on the Capital One Venture Rewards Credit Card, this could also be a good way to get some nice hotel stays on the cheap.

That’s it for today, my friends. I hope my own bad travel experiences have given you some confidence to advocate for yourself.

As always, have a wonderful day, and I’ll see you tomorrow. 🫡

6.9175° S, 107.6191° E

With contributions by McKay Moffitt, April Wilson, and Alison Carrico