I’m guilty of a points & miles crime

Good morning and welcome back to Daily Drop — the newsletter that shows up every day with no blackout dates and unlimited carry-on baggage (emotional or otherwise).

Here’s what I’ve got today:

• ✈️ AA revamps mileage upgrades

• 👨‍⚖️ Points & Miles Court (I’m guilty)

• 🌎 Get inspired with Matador Network

• 🏨 Save on hotel award stays this summer

• 🏡 How to use Airbnb like a pro

✈️ AA revamps mileage upgrades

Last week, American Airlines dropped some big news related to mileage upgrades. Some people love it, some hate it.

Let’s break it down, and you can decide for yourself.

Starting immediately, American Airlines is offering instant upgrades using miles (in addition to cash, which it has done for a while).

So when you get an email like this one asking if you want to upgrade, you’ll have both options:

The catch?

The redemption value is, as we say in the biz, “very bad.” You’ll get less than one cent per point. 😬

American Airlines miles are generally worth much more than that, often double. So this is not an optimal way to use your miles.

But there are two silver linings:

First, you can still use AA’s upgrade award chart until August 12 at midnight (CT). This means you can upgrade your flights for as few as 5,000 miles. 🙌

Secondly, upgrades are way easier now.

While the value is bad, you don’t need to play games to get into the fancy seat — just click your offer, pay the miles, and get an instant confirmation.

If you have any AA flights booked that you'd like to upgrade, I suggest calling AA and locking in your requests under the current award chart before the August deadline.

And if you’re excited about the change and want to rack up a stash of AA miles, consider signing for an AA co-branded credit card.

👨‍⚖️ Points & Miles Court: Case of the unstacked stay

Welcome to Points & Miles Court, where miles are sacred, and credit cards are worshipped. Today’s defendant? Me.

🕵️‍♂️ The Crime

I booked a three-night hotel stay at an IHG property in Sapporo, Japan, using cash. Seems simple, right?

I even used my IHG One Rewards Premier Credit Card — solid move, 10x points, feels responsible. Until I remembered something after checking out…

I had a merchant offer on the American Express® Gold Card from a different bank: $50 statement credit for spending $250+ at IHG hotels… in Japan. 🤦‍♂️

And what was my total bill? You guessed it — $255. The irony? I literally teach people this stuff for a living.

But it gets much worse than that…

In my usual rush to rebook on my phone, I also skipped the obvious next move: clicking through a shopping portal.

No Rakuten, no Capital One Offers (both of which were offering 5-10% back at IHG).

📉 The Damage

• Missed merchant offer: –$50

• Missed portal earnings: ~$5–10 worth of points or miles

• Total losses: Let’s call it a fancy sushi dinner

• Emotional harm: Mild, but deserved

🧠 The Takeaway

Always, always check for merchant offers on popular travel cards before booking paid travel — especially for chain hotel brands and popular airlines, which regularly have offers from one bank or another.

Earning $50 cash back (a 20% rebate in my case) will ALWAYS be the optimal move – even if the card in question has terrible earning rates.

Also? Install a browser extension like Rakuten. It’s a simple reminder to stack with a portal whenever you’re not booking with points.

⚖️ Court Is Now in Session

Have you committed a similar travel crime?

Confess your sins, and I’ll choose one of your responses to discuss in a future newsletter so others can learn from our mistakes.

🏨 Save on hotel award stays this summer

There’s only one thing better than a free stay booked with points: a free stay booked with even fewer points.

Speaking of IHG…

Until August 31, you can get a 15% discount at new (and renovated) IHG hotels and resorts around the world when using IHG points.

There’s a specific list of properties that this sale applies to, with well over 50 hotels in the U.S. and many dozens more in Europe and elsewhere.

There is some fine print to be aware of:

• This deal does not stack with the 4th-night free perk from IHG co-branded cards

• Only available on stays booked with points

• Different hotels have different eligible stay dates (clearly laid out on this page)

Overall, the timing is perfect for summer travels, whether at home in the U.S. or abroad.

For example, this new Voco hotel in Flagstaff, Arizona, is perfect for a nice wellness getaway and costs less than 14,000 points per night during the sale:

As I mentioned, there are plenty of hotels abroad in popular destinations that are also part of this sale, including:

• 🇯🇵 ANA Holiday Inn Tokyo Bay

• 🇯🇵 ANA Crowne Plaza Resort Okinawa

• 🇲🇹 Voco Malta

• 🇩🇪 Kimpton Main Frankfurt

• 🇵🇪 SOUMA Lima, Vignette Collection

• 🇻🇳 Voco Quang Binh Resort

Anyway, check out the sale page to see a full list of properties and consider locking in some cheap points stays this summer.

🏡 How to use Airbnb like a pro

Hotel and airline programs are great. I love me a good cheap award stay with free breakfast.

But sometimes, it’s nice to feel more like you’re at home when traveling — and that’s where vacation rentals like Airbnb come into play.

In this week’s Daily Drop YouTube video, we’ll teach you how to use Airbnb like a pro… and even book them with points. 😉

That’s all for today, amigos! I hope you learned a little something today (and maybe even had some fun).

Let me know if you enjoyed my little courtroom drama, and good luck surviving your Monday morning.

Deuces ✌️

6.1944° S, 106.8229° E

With contributions by Tiffany Eastham, McKay Moffitt, and Benji Stawski