Hello from NYC!

I’d normally say the holiday season is one of the best times of the year to visit New York, but this year feels different.

One, it’s so much colder than I remember for December. (Even my iPhone reminded me yesterday that it’s 10 degrees chillier than average.)

Two, Jill and I are just coming off of one of the best trips we’ve ever taken. More on that below.

Before that, just a few housekeeping notes.

You’ll notice it’s Wednesday, and this is already the second newsletter to hit your inbox this week. I promised I’d experiment with different candences, and this week is a busy one, so this likely won’t be the last.

Finally, welcome to all the new subscribers! I know some of you are here for my giveaway update. You’ll find that, as well as a ton more important updates below.

Have you ever visited a place years ago and spent the next decade dreaming about going back?

That’s exactly how I felt when I left the Four Seasons Costa Rica in June 2013. I was 20 years old, fresh off a family trip, and convinced this was the nicest resort I’d ever stayed at.

I remember frequently scrolling back through those pictures, hoping I’d get to return soon.

I didn’t expect it to turn into 12 years, but here we are.

Jill and I just got back from a fantastic, hosted stay at the property, which — I can confirm — exceeded my memories and remains Costa Rica’s top luxe option.

Since my last visit, the property had had a big glow-up (we especially loved the new hillside open-air wellness shala). Plus, our signature couples’ day will keep me scrolling through my camera roll for years to come.

Want a peek at our stay? I have lots more to say, including why Costa Rica may be a better (and just as convenient) alternative to lounging on the beach in the Caribbean.

And for nostalgia's sake, I even dug up a photo of my 2013 outfit and my first-ever room “tour.”

Shopping for holiday gifts is (surprisingly?) one of my least-favorite activities.

Even though I try plenty of tech, gear, and lifestyle items each year, I always find it stressful to pick the perfect gift for everyone on my list.

Well, if you feel the same way, I’ve got good news. I just compiled a guide with my top 20 holiday gifts for every type of traveler.

Some top picks include:

AirTags are the single best stocking stuffers for travelers.

Amazon’s even got a nice sale on the four-pack. They’re regularly $99, but grab them for just $74.98 today.

Away makes great lifestyle and travel gifts.

My go-to travel backpack is the Commuter Backpack, and I also love Away’s small toiletry bags and their packing cubes.

If your loved one already has a pair of AirPods, then your job is to ensure they have an AirFly to connect them to the seatback screen.

Whether they’re stuck in the middle or riding in premium economy, a travel pillow always comes in the clutch.

My go-to recommendation is from Trtl. Buy for $48.73 on Amazon.

Even if you hate my recommendations, don’t forget to start your shopping journey at Rakuten.

It’s a cash-back portal that gives you a cash (or points) rebate at more than 3,500 brands. You click your preferred store on Rakuten, then shop as usual.

Wait a few days, and cash will be deposited into your account.

You can get $50 when you sign up and then shop with my referral link.

Speaking of holiday shopping, I nearly bought my daughter her first holiday gift on my way home from Costa Rica.

The local version of Hudson News at Liberia International Airport was selling toy airplanes.

I have fond memories of playing with these as a kid. Jill doesn’t want me to turn our daughter into an avgeek just yet, but little does she know I discreetly purchased an Iberia jet when she was in the bathroom.

(Pro tip: remove the wheels on the plane before giving it to your kid. I’ve heard they sometimes try eating the wheels.)

This week began with some (mixed) news that I had predicted earlier this summer: United will price PlusPoints upgrades dynamically starting in 2027.

The airline shared only 45 words about the move in a customer email, which is far too few for me (and should be for you, too).

So I turned to Luc Bondar, the airline’s loyalty chief, to spill the beans about the backstory and what to expect.

He dropped some juicy details, including when he first started considering the move to dynamic. (Spoiler: it was way earlier than I thought.)

I asked you to tell me what you thought about United’s new controversial flight status displays, pictured above.

I initially expected everyone to ask for the old ones back (like I did), but boy, was I wrong.

My favorite reply was from a subscriber who said, “I’d imagine United tested this with focus groups before rolling it out and presumably got positive feedback.”

If you’re a company looking to fill a focus group or need some consulting help, my inbox is always open. (I honor non-disclosure agreements, btw).

And for the record, no, I wasn’t consulted about United’s new TVs before they started popping up everywhere.

I posted on Instagram yesterday to announce the return of my annual holiday upgrade and free hotel night exchange.

This year, it’ll be limited to newsletter subscribers, and I’ll share updates here as I have them.

I only received 880 PlusPoints and eight Hyatt club upgrade awards so far.

I need a few more donations (especially from Global Services members) to launch the exchange, so please check your accounts and ask your friends to donate. I’m looking for United PlusPoints, American systemwide upgrades, and hotel free night certificates.

As always, there have been some recent developments that have piqued my interest.