Happy New Year!

While my heart is full from all the family time over the holidays, I'm ready to get back into the swing of things

Judging by how few people were out on the streets of NYC yesterday and today, it seems not everyone is ready to call the holiday season quits. (Or maybe they’re just all stuck in the Caribbean.)

Either way, it’s good to be back in your inbox, and I’m looking forward to what 2026 has in store.

For me, that’ll mean more travel, lots more content, and some fun opportunities along the way.

(Speaking of fun opportunities, if your company is looking for creator partnerships, newsletter sponsorships, or even needs a travel expert to speak on a panel, I’m your guy.)

Table of Contents

Free upgrades

I know many of you want to know the latest about my annual United upgrade spree.

Well, I’m digging through lots more submissions, and I promise to get through them shortly. As always, I prioritize long-haul flights and try to spread the love as much as possible.

Here are the latest stats.

  • 2,520 PlusPoints redeemed

  • 51 upgrades processed

  • 65 flyers upgraded

  • Longest flight: Newark to Johannesburg

Now that the calendar has turned to January, let me know if you’re a United Premier with expiring PlusPoints. I promise they’ll get put to good use.

Booking flights — the right way

I may consider myself a travel expert, but I still love learning new things.

Last month, I learned about a more rewarding way to book United flights.

If you book United flights via the Bilt travel portal, you earn an extra point for every dollar you spend.

That’s on top of the credit card points you earn from airfare spend. And you get a direct booking, meaning that you can make changes and cancellations directly with United. And still earn full United miles and Premier credit.

Bilt accounts are free, and there’s no special Bilt credit card or rental apartment required either.

And as always, after you book, remember to add your flights to your Autopilot account to track for price drops.

176/179 to board

Over the past two weeks, we’ve taken our one-year-old daughter on four flights. (Yes, we all survived, including our nearby seatmates.) And we have also perfected a new travel routine.

First, we only fly during her naptime. (When she’s awake, her favorite activity is to play slam-the-screen on the seat in front, which isn’t exactly a fun game for our neighbors.)

When we travel with her, we also check all of our wheeled bags, including the carry-ons. Then, we board dead last.

There’s no reason our daughter needs to spend extra time in the confined metal tube, even if it means that daddy won’t get great pictures.

And with travel mode on United’s updated mobile app, we know exactly where we are in the boarding line. Yesterday, we waited until 176 fellow passengers had boarded the Boeing 737-900 for us to be the last three on board.

Finally, if you’re a parent without the Doona car seat/stroller combo, you’re missing out. We’ve used the Doona religiously since our daughter was born.

It converts between an FAA-approved car seat and stroller, and we bring it everywhere. (Sadly, our daughter is about to grow out of it.)

We also bring the Bugaboo Butterfly 2 with us on longer trips because it’s both super portable and very comfortable.

Damaged goods 😬

So yes, call me crazy, but now we’re a family that checks bags.

And we’re also the proud owners of a damaged Rimowa Essential bag, which was delivered on the JetBlue bag carousel at Fort Lauderdale airport. (Who knew these things could break?)

I’ve actually never had a bag damaged in transit before, but we received the bag as a wedding gift in 2021. It looks like Rimowa offers a five-year guarantee for bags purchased pre-2022, so I’ll report back on how we end up getting it fixed.

Speaking of damaged goods, I need to plug Rag and Bone for a second.

I love their jeans, but I especially love their quality guarantee. Last week, a pair of my jeans ripped. Now they’re on their way back to the brand, and a replacement pair is on its way to me — no questions asked.

Let’s hope Rimowa is as helpful as Rag and Bone.

Free luggage carts

Why pay $7 for a luggage cart at baggage claim when you can get one for free?

Just go outside to the curb and grab one of the unclaimed carts that weren’t returned.

Now that we’ve been checking bags, this is my favorite easy travel tip that no one is talking about. (Here are my others.)

Hotel smoking scam

If you’re new here, you might’ve missed the viral smoking scam that happened to me over the summer.

I was charged a $500 smoking fee in a room I never smoked in. Turns out, so were many others — at the exact same hotel. (The hotel blamed the $500 charge on a smoking report issued by an AI-powered smoke detector from Rest Sensors installed in every room.)

Even worse, I investigated other hotels that use Rest Sensors, and guess what? I uncovered scores of other similar complaints about seemingly fraudulent smoking charges at other hotels using the Rest Sensor.

And, to no one’s surprise, it seems nothing has changed. A follower just passed along his experience getting incorrectly charged a $500 smoking fee at the Palazzo in Vegas. It went viral on Reddit.

The first thing you need to do in a hotel is check the smoke detector and then the shower water temperature.

News you can use

  • Delta abandons NY airport: Small regional airports continue to struggle post-pandemic. This time, it’s Binghamton, which is losing all scheduled commercial service. Yikes.

  • Caribbean mess: Saturday’s FAA-mandated airspace closure led to hundreds of cancellations across the Caribbean. Rough timing with all the holidaygoers looking to get back home. Fortunately, the airspace reopened on Sunday, and airlines have added thousands of extra seats to get you home. Think you have a crazy story? I’d love to hear it. Just reply to this email.

    • As a side note, I found it interesting that Puerto Rico flights were canceled while Punta Cana service was entirely unaffected — despite being just under 100 miles apart.

  • American’s centennial is here: American Airlines turns 100 this year. Mazel tov! The airline says it has lots of celebrations planned, starting with a new special livery, as seen below. Call me crazy, but I actually like some of the new centennial-branded AA gear. And you can even get a limited-edition Citi cobranded card with the 100 logo.

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