Major (pretty good) updates from Hilton

Good morning and welcome back to your Friday edition of Daily Drop.

We’ve got a lot to cover today, so let’s waste no time:

• 🏨 Major (pretty good) updates from Hilton

• 🤩 Did someone say (early) Black Friday sale?

• ✈️ How to book literally anything with points

• 💙 Blue Friday Sale Is Back

• 💳 Current Transfer Bonuses

🏨 Major (pretty good) updates from Hilton

Hilton finally did the thing we’ve all been expecting them to do someday: burn their entire elite structure to the ground and rebuild it from scratch.

And honestly? It’s… surprisingly decent.

Starting January 1, 2026, Hilton Honors is getting a huge overhaul: a brand-new ultra-elite tier, easier qualification for existing tiers, a more logical spend-based system, and the death of rollover nights (RIP).

Let’s walk through what’s actually changing — without turning this into a loyalty-program autopsy.

Diamond Reserve: the new “you practically live here” tier

Hilton added a brand-new tier above Diamond called Diamond Reserve, which is basically “corporate road warrior” status.

You can’t get it directly from a Hilton credit card – you have to earn it with real stays AND real spend.

To qualify in a single year, you’ll need:

• 80 nights or 40 stays, and also

• $18,000 in eligible Hilton spend

So the vibe is very “I haven’t seen my own home since March.”

What you actually get for all that effort:

• A 120% points bonus (nice)

• A Confirmable Upgrade Reward you can use at booking (finally!)

• Guaranteed 4 p.m. late checkout at most properties (keyword is “guaranteed”)

• Access to Premium Clubs (at the handful of Hiltons that even have them)

• A special support line that presumably answers the phone faster than the normal one?

Plus, everything that regular Diamond members get.

Gold & Diamond are about to get MUCH easier

Here’s where normal humans benefit:

Hilton is dropping the qualification requirements for Silver, Gold, and Diamond starting in 2026. Nights and stays go down, and Hilton is replacing the “base points” path with a simpler spend path.

To recap the current requirements versus 2026 requirements, here is a sexy chart:

The TL;DR is simple:

If you’ve ever been close to earning Gold or Diamond the “hard way,” 2026 is going to feel like Hilton just noticeably lowered the bar.

Milestone rewards are leveling up a bit

Hilton already has milestone bonuses, but they’re adding something spicy: the Confirmable Upgrade Reward.

You’ll earn one:

• Automatically, when you hit Diamond Reserve, and

• Again as a milestone at 120 nights, even if you’re not Reserve

It’s not as generous as what other programs offer at that level, but hey — for Hilton, having any confirmed upgrade is a major plus.

And yes… a couple things are getting worse

Most notably, rollover nights are dead. ☠️

2025 is the LAST year where extra nights carry over into the next year. After that, your counter resets every January like it’s New Year’s at a crappy gym.

Also, Hilton still has the classic Hilton problem: some hotels treat elite benefits like folklore. So, while the new structure looks cleaner on paper, how consistent it feels around the world? TBD.

With Diamond and Gold status being easier to earn, you’ll also have to assume there will now be more elites competing for the same benefits.

So what does this actually mean for you?

Here’s a basic rundown. If you:

• Earn Gold or Diamond through co-branded credit cards → Nothing bad happens to you. In fact, Hilton lowering the requirements makes your card-based status feel more “aligned” with the program, if we’re being honest with ourselves.

• Stay 25–50 nights per year → You’re the big winner. Lower requirements + milestone rewards make 2026 greener than 2025.

• Travel enough to sniff Diamond Reserve → Congrats on your perma-jetlag. You’ll finally get a tier that acknowledges how much you suffer for points.

🤩 Did someone say (early) Black Friday sale?

Since we’re all apparently doing our holiday shopping in late November like responsible adults (for once), here’s something worth tossing in your cart:

From November 21–27, you can get Daily Drop Pro for $99 for your first year, plus a free airport t-shirt (eeeekk, yay!).

No fine print — just an amaaazing price and a shirt you can proudly wear while you’re traveling home for the holidays (and I mean… you can wear it after that, too). 

If you’ve been thinking of joining Pro, this is the week to do it. 

Your 2026 travel self will thank you. 

✈️ How to book literally anything with points

There’s a secret points trick that, in my opinion, is underrated. I’ve been telling you about it for years now, but it’s time for a refresh:

You can use Capital One miles to cover any travel purchase at a flat 1 cent per mile.

And when I say “any,” I mean any:

Cheap flights you found on some janky third-party website? Yep. A hostel in Slovenia? Sure. A ferry ticket? Train ticket? Airport shuttle? Taxes on an award ticket?

Swipe your card → let it post → wipe it away with miles.

This is why Capital One miles are low-key one of the most flexible currencies in the entire game.

You’re not hunting for award space. You’re not stuck booking through a portal. You just find the cheapest price anywhere on the internet, book it with your Capital One card, and cover the charge after the fact.

Is it always the highest cents-per-point value? Nope.

But because you can book the cheapest possible option from any travel site, there are many cases where doing it this way will cost you fewer overall points – so who really cares about “cents-per-point” value?

And right now, the timing could not be better because…

The Venture X is offering 100,000 miles

I know, I know. We sound like a broken record. But the offer is that good. And I want you all to have lots of miles.

100,000 Capital One miles from the Venture X is worth $1,000 in travel, or more if you transfer to partners — and yes, those same miles can also cover random travel purchases for 90 days after they post.

If you want the full walkthrough (and some very fun examples), here’s the full article:

SPONSORED BY LA COMPAGNIE

💙 Blue Friday Sale Is Back

If you’ve ever stared at a long-haul economy seat and thought, “Surely there’s a better way to do this,” I’ve got good news for you.

Just in time for 2026 travel planning, La Compagnie — the all-business-class airline flying between Newark and Europe — is back with its annual Blue Friday sale.

And this year’s pricing is the kind of thing that makes even us pause our points game and say… ok, this checks out.

Here’s the deal:

• Round-trip fares to Paris or Milan from $2,400

• Round-trip fares to Nice from $2,700

• Available on select flights December 1, 2025, until May 31, 2026

• Book from November 21–28, 2025

No complicated rules. No weird blackout dates. Just a genuinely strong price for lie-flat seats, champagne, a thoughtful dining experience, and unlimited high-speed Wi-Fi, which even legacy carriers don’t reliably offer in their premium cabins.

If you’ve been sitting on plans for a milestone trip, want to skip the award-space treasure hunt, or simply don’t have a giant points balance to work with, this is one of those cash fares that makes sense for you.

Not to mention — this is just a wicked cool and unique experience.

Business class on major U.S. carriers often starts around $3,000, not including sky-high taxes and fees you’d still owe even when booking with miles. That’s why this sale tends to sell out fast.

So, if Europe is even loosely on your radar for early 2026, here’s your chance. Book during the sale window and lock this one in, friend.

And that finished off the week, my friends! By the time you read this, I’ll be in Lanzhou, the famous noodle city. 🍜

But when you hear from me on Monday, I’ll be somewhere else. Stay tuned to find out where.

Cheers,

36.0614° N, 103.8342° E

With contributions by McKay Moffitt