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How to book a free stopover

How to book a free stopover

And how to take advantage of this perk to book really interesting trips!

Rachel Lipson's avatar
Rachel Lipson
May 21, 2025
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How to book a free stopover
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Some quick notes before launching into this post today — that is one of the most requested posts to date! I am so excited to share this info with you all.

But first!

TODAY (Wednesday) at 1:00pm ET is the webinar I am co-hosting on wills and trusts for families with Steward, the modern estate planning company.

There are prizes you can win by registering such as: a $300 gift card to LILIA, a 1:1 points coaching session with yours truly, and more!

If you sign up for a comprehensive estate plan with Steward, by attending this webinar you’ll get $1,000 off the $3,000 package (through 5/31 only)!

Don’t miss this! It’s huge and Steward does incredible work.

I have been so happy to see how many of you have signed up. I can’t wait to see your faces! Please try to make it live if you can since the deadline for the discount is in just 10 days — though there will be a recording for anyone who can’t make it.

Please register here to join!

Now, on to points stuff!!

A friend of mine pointed out how we always tackle multiple cities and countries on our trips. And it’s true! Every trip we’ve taken to Europe has been a multi-city trip and I can hardly help myself!

Some trips we’ve taken:

  • Budapest » Vienna » Prague

  • Madrid » Barcelona » Costa Brava

  • London » Paris » Copenhagen

  • Amsterdam » Berlin » Paris

And there have been more!

Once we are spending the money/points to go abroad, it feels like we’re getting even more bang for our buck by fitting in a couple places instead of just one.

I’ve never been someone who checked cities or countries off of a list — I really value the experiences of seeing new and different places and love finding opportunities to make that happen.

One way I’ve been able to book multi-city trips is by using the free stopover benefit on award bookings that some airlines have.

I mentioned this on Instagram while talking about one of my last trips and so many people had questions! I’m excited to share this intel and simplify something that can seem pretty overwhelming (like most things points related!).

First, a quick explanation on the difference between a layover and a stopover (just to be sure we’re all on the same page):

What is a layover?

A layover is when you stay for less than 24 hours in a city between flights for an international flight and less than 4 hours for domestic.

What is a stopover?

A stopover is when you spend more than 24 hours (or 4 hours for domestic) and get to actually spend time in the city instead of just passing through the airport.

Some airlines offer these stopovers at no additional cost. Knowing how to take advantage of this perk can enrich your trips, open up new possibilities and save you some real money.

Why book a stopover?

One of my favorite family travel tips is to book a stopover! Even if it’s just one night it can be really awesome and can beat dealing with a short layover, stress about missed connections, etc.

One of the best experiences we had on our spring break trip 2024 was the 24 hour stopover in Amsterdam on our way home from Budapest, Vienna and Prague.

Another excellent use of this benefit was our flight home from Berlin to NYC this last spring break. Instead of a layover at Charles de Gaulle in Paris — an airport where we’ve had relatively impossible connections in the past (more on that another day), we stayed in Paris for 2 nights without paying extra.

It really rounded out an incredible trip. If we’d gone straight home from Berlin, we would have missed some of the best parts of that adventure.

The three kinds of stopovers:

  • The sleepover: A night or two in a different city to split up the trip and make the flights/connections a little easier and more predictable

  • The vacation: A strategy to book a multi-city trip (with the stopover as an intentional destination)

  • A save for later: A one way ticket to hang onto and use at a later date

This post will teach you:

  • Some of the airlines that offer free and low cost stopovers

  • The airline that doesn’t advertise free stopovers (but actually is one of the best!)

  • The inside scoop on how to book a stopover (with said airline) using points!

  • Bonus: a few of my favorite cities for stopovers and hotels we love in each city.

Read on! Don’t miss this one!

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