How to book a free stopover

Good morning from Toronto - where the skyline is tall, the bagels are underrated, and I say “sorry” about everything, even when it’s not called for. 🇨🇦🍁

Here’s what we’ve got today:

• ✈️ How to book a free stopover

• 📊 Poll Results: Y’all are predictable

• 🤓 Travel Trivia Tuesday

✈️ How to book a free stopover

We all know Alaska has been on the up-and-up recently. But there’s one excellent feature about Alaska that has been around forever…

I’m talking about the ability to add a free stopover on award tickets - something that few airlines in the biz offer.

Given all of the new features of Alaska, I want to walk you through how exactly to find and book free stopovers with Alaska.

For starters, a stopover is when you spend more than 24 hours between flights, or even days… or weeks.

If it had a Tinder profile, it’d be ‘looking for something serious’ - while a layover is more of a ‘here for a good time, not a long time’ kind of situation.

(Don’t ask why that’s fresh on my mind.)

Anyway, there are some rules to be aware of when booking a stopover with Alaska:

• Only one stopover per direction is allowed (two for a round-trip booking)

• You must be flying on an international itinerary (no stopovers on domestic flights - sorry, Boise)

• You cannot fly more than one partner airline (though you can mix in flights on Alaska itself in addition to said partner)

Honestly? This is one of the best stopover policies out there.

And with Alaska’s spicy lineup of partner airlines, this trick opens up tons of incredible redemption opportunities.

So now that you know why it’s great, here’s how to actually do it.

First, you’ll want to navigate to Alaska’s website.

On the home page, you’ll need to click “All Search Options,” the little link they don’t want you to see. 😉

From here, you simply toggle the boxes for “Multi-city” and “Use miles,” input your desired routes, and you’re good to go.

For example, let’s say you want to spend a week in Ireland and then head to Budapest from there.

You can run a search for New York (JFK) to Dublin (DUB) on May 5th, then from Dublin to Budapest (BUD) on May 13th.

Sure enough, you can book this exact itinerary for just 27,500 Alaska miles and $33 in taxes and fees. 

Epic. 👇

And just to prove the stopover doesn’t cost extra, I ran a separate search for New York → Budapest with just a two-hour layover.

The price? Exactly the same.

Here’s why Aer Lingus is one of my favorite stopover options:

They have tons of U.S. routes, solid award space, and a great European network - so you can easily turn a single redemption into a full-on Eurotrip.

But you can use this for some longer, more expensive flights, too.

For example, you can fly from Los Angeles (LAX) to Sydney (SYD) and then onward to Auckland (AKL) for a grand total of just 42,500 Alaska miles and $151 in taxes and fees, all flown on Qantas:

Considering how far away these countries are and how expensive cash rates are in Oceania, this is a great way to get serious bang for your buck.

Don’t forget that right now, it’s still possible to transfer Membership Rewards Points to Alaska (via Hawaiian) at a 1:1 ratio.

We expect this transfer opportunity to disappear in the near-ish future, so I personally emptied out my stash of Membership Rewards Points for exactly this.

Happy stopover hunting!

📊 Poll Results: Y’all are predictable

Wow. I asked you how you’d rather spend your hard-earned points, and I gotta say… the results were absolutely NOT shocking. 😆

First class won in a LANDSLIDE.

With 59% of the votes, y’all saw the words caviar at 40,000 feet and lost your collective minds.

Over 1,100 of you declared that being gently cradled in a lie-flat seat while sipping champagne is the only way to travel.

And honestly? I respect it.

And then, in last place, we have the few degenerates who picked “something ridiculous” (aka, blowing all their points on an Emirates first-class)

Honestly? You’re the real MVPs. Respect.

Anyway, thanks for participating, y’all. I’ll try to come up with something a little more controversial next time to keep it interesting. 😉

🤓 Travel Trivia Tuesday

And the correct answer is… Korean Air! 🇰🇷✈️

For the first time, Korean Air snagged the top spot in AirlineRatings.com’s Airline of the Year awards, dethroning Qatar Airways from its long-held number-one ranking.

So, what makes Korean Air the best in the world, you ask? For starters, it resisted the trend of cramming more seats into its planes—specifically keeping a roomier 33-34 inch seat pitch on its Boeing 777s.

Which means? More legroom for economy passengers!

It’s not just about space, though. Korean Air also gets praise for its service, generous on-board meals, and top-tier in-flight entertainment (plus some Bluetooth connection on the new planes).

Other big winners in this year’s rankings included JetBlue, which took the Best Hybrid Airline title, AirAsia, which won Best Low-Cost Airline, and Virgin Australia, which claimed Best Cabin Crew.

Curious which airlines made the Top 10 Best Full-Service Airlines list for 2025? Check it out here.

Would you book a flight on Korean Air just for the legroom? Or are you still holding out for that elusive Qatar QSuite upgrade? 👀

Check out this great win from one of our Daily Drop Lounge members!👇

Want to join in on the fun? Join our Facebook community, the Daily Drop Lounge.

That’s all for today, folks! I hope you enjoyed a solid points and miles trick, some data from your fellow Daily Drop comrades, and some fun trivia.

I’ve got a really fun newsletter in the works for tomorrow, so be sure to tune in.

Until then,

52°22'35.4"N 52°15'17.4"W