Why I'm planning more stopovers in 2026

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In 2025, most of my trips were somewhat one-dimensional. I went from point A to point B, one city, done. That works when you’re short on time, but looking back, I think it was a missed opportunity.

So in 2026, I’m making a small change that can make trips feel bigger without costing much more: I’m booking more stopovers.

A stopover is a layover you choose on purpose. Instead of a quick connection, you build in a real break (usually 24 hours or more) in your connecting city, then continue on the same ticket. Sometimes it’s free, but even when it costs extra, it’s often cheaper than booking a separate flight.

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Stopovers let you visit a bonus city on trips you were already taking anyway.

They’re also game-changers when traveling with a pet (hi, Pretzel) or kids. Ten straight hours in a carrier, or a marathon travel day with a toddler, is a lot. Splitting the journey into two shorter days with a real break in the middle is much more manageable.

The real magic is how some airline programs price these awards. Instead of charging you for two separate trips, they price the whole thing as one itinerary and let you “pause” along the way.

Take this sample Air France economy flight from New York to Athens with a three-day stop in Paris:

• Booking separately: New York to Paris (25,000 miles) + Paris to Athens (10,000 miles) = 35,000 miles
• Booking as one multi-city ticket: 25,000 miles total

You’re essentially getting two vacations for the price of one.

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Alaska has long allowed a stopover on one-way awards, and luckily, that perk has carried over into the new Atmos Rewards program. Even better, you can book these online using the multi-city search.

The key is routing. These stopovers are designed for bigger trips between regions. So, if I were planning my bucket list trip to Australia, I could fly from New York to Los Angeles, stop for a few days to see family, then continue to Sydney without spending extra points.

It’s also another reason to love Bilt points, since they transfer to Alaska at a 1:1 ratio.

Flying Blue offers free stopovers on award tickets that can last from 24 hours up to a year. The catch is that you typically have to book these by phone.

This works perfectly for me, since I regularly visit family in Germany. I can turn a simple trip into a mini European adventure like this:

• New York to Frankfurt, with three days in Paris on the outbound
• Frankfurt to New York, with two days in Amsterdam on the return

Flying Blue miles are also easy to stockpile because it’s a transfer partner of most major transferable points programs.

Aeroplan charges a flat 5,000 extra points to add a stopover to an award, as long as the stopover city is outside the U.S. and Canada. Stopovers start at 24 hours, can last up to 45 days, and you can book online using the “Multi-city/Stopover” option.

Aeroplan has some useful airline partners beyond the Star Alliance, such as Emirates, and also partners with most major transferable currencies like Amex Membership Rewards, Chase Ultimate Rewards, and Capital One Miles.

Between crediting oneworld flights to JAL over the years and being able to transfer points from Bilt, I’ve built a decent stash of Japan Airlines Mileage Bank miles.

These are especially useful for multi-city trips because partner awards are priced by total distance flown. That means you can sometimes add a stop without increasing the mileage cost, as long as you stay in the same distance band.

Partner awards under 1,000 total miles start at 12,000 miles in economy. At that rate, I could book a fun Northeast loop like this: Boston to New York, New York to Washington, D.C., Washington, D.C. to Syracuse, and Syracuse back to Boston.

You can use the same idea on the West Coast, or even string together a few cities within Alaska.

Stopovers aren’t just for award tickets. For example, TAP Air Portugal lets you add a free stopover in Lisbon or Porto for up to 10 days on cash fares.

Some airlines even add perks to encourage you to visit. Turkish Airlines, for instance, offers free hotel stays for eligible international connections.

If 2025 was my year of efficient travel, 2026 is my year of better travel. If I have to connect anyway, I might as well get an extra passport stamp and a calmer travel day for my dog Pretzel.

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