Flying internationally is expensive and adding additional destinations to your trip often seems daunting. However, did you know that you can use connections and stopovers to your advantage when booking a flight? In this video/post, we’re going to explore the popular 23:59 rule and show you how to book long stopovers. This will allow you to see more with less money!

Defining a “connection” and “stopover”

The words “connection” and “stopover” often have a negative connotation. People associate them with long periods of waiting at the airport for their next flight. I often shy away from connecting flights and select non-stop flights to avoid the hassle of changing aircrafts.

However, any connecting flight that is under 24 hours counts as a “connection”. Anything above 24 hours is a “stopover”, which usually results in an extra charge. The concept is to incorporate connections that are just under 24 hours. These connections feel like stopovers, but are technically connections. This is known as the 23:59 rule!

How to use the 23:59 rule?

Suppose you fly from Los Angeles to Bangkok, but you stop in Taiwan. If you time your arrival around mid-day, it’s possible to visit the stopover city during the day and fly out the next morning. You can place your belongings in a locker, or check into a hotel for the night. Some people will even try to land early in the morning so they can explore during the day and return to the airport for a night flight. This allows them to avoid paying for a hotel too.

Airlines that promote stopovers

Even though 24-hours is the general limit for what counts as a stopover, there are several airlines that allow and often promote longer stopovers.

For North America stopovers, check out Air Canada’s stopover policy for return flights.

For Europe, check out: 

For Asia, check out:

For Africa and the Middle East, check out:

We traveled to Lisbon last year during the winter holiday, and if we had more time, we would have loved to take advantage of TAP Portugal’s overnight layover offer and policy. It would have been a great way to see other cities in Portugal like Porto.

How to book a flight with a stopover

There are a few ways to book a trip with stopovers. However, it can require a bit of research. Most times, you would search for a flight on sites like Google Flights or Skyscanner, then see if there is a common stop location. For example, if we look at the Los Angeles to Bangkok example, there are a lot of flights that stop in either Beijing and Taipei. Since several Air China flights stop in Beijing, you can create a multi-city flight that gives you a day or two to explore Beijing. 

Still, there is a better way to search for these flights. You can use a tool designed for this exact purpose. A popular one in the travel community is Air Wander. Air Wander basically does a lot of the heavy lifting for you in finding flights and destinations based on the stopover locations and length of time. It even has a special interface that will tell you where you can stopover and for how much more than the regular direct flight. The filter lets you specify how long you want to stay at your connection for each individual leg of your trip, which makes it so much easier when trying to design a flight plan with stopovers.

For example, you may want a long connection when you’re traveling to your destination. Though on your way home, you may want a quick connection or direct flight. The tool allows you to specify your preferences.

And just in case you’re wondering, I did the same search for a stopover in Beijing on Air Wander, and it found the same flight plan that I was able to create on Skyscanner.

Additional tips and considerations

Below are some additional tips to keep in mind when booking flights with long connections or stopovers:

1. Check visa requirements:

If you’re planning to explore a new city during your stopover, make sure you have a valid visa for that country. Most times you’ll get flagged at the airport if you don’t have a visa for your final location, but stopovers can often get overlooked. Make sure you do some research ahead of time on whether you need one. Getting a travel visa can be a simple or complicated process, depending on the country.

2. Use airport lockers:

If you’re planning to leave the airport, but planning to return on the same day, consider using an airport locker. Most airports have them, or offer some kind of similar luggage hold service. Some airlines will also let you check in a bag 24 hours in advance, which is another option if a locker isn’t available.

Ironically, LAX, which is the closest international airport to me, doesn’t have luggage lockers. Instead, there is a company called LAX Luggage Storage which will hold your bag for a fee.

3. Point redemptions can be limited and difficult:

When booking flights with longer stopovers, it can be a challenge to book them using points, even if they are an official travel partner to your points program. If you’re determined to use points, I suggest calling your points program to see if you can book over the phone if you can’t find the same or similar flight plan. For example, Chase lists a 24-hour support line if you need help booking via their travel portal.

4. Know your limits:

Coming off a long flight and spending an entire day touring a city, then jumping onto another flight can be tough on the body. This is especially true if you’re not able to rest or sleep on the plane. As someone who often struggles with red-eye flights, remember not to overextend yourself. The last thing you want is push your body too hard and get sick during your trip.

Have you used the 23:59 rule, or even booked an extended stopover during your travels? If so, let us know how you did it or if you have any tips on the process.

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