a woman standing in a plane

There are a few ways to measure a good trip. For some people, it’s the amount of photographs taken. For others, it’s the stories and random happenings along the way.

You’ve undoubtedly heard the saying “when life gives you lemons, you should make lemonade”, and there’s no challenge to that here. But I am here to tell you that when life gives you horrendous flight options, if you make them even worse, they can really and truly create a highlight of a trip.

It’s all about the 23:59 rule, which is an opportunity to stretch what could otherwise be an annoying connection, into one long enough to savor. And crucially, leave the busy airport.

Helping a friend book a hectic trip this week, I was reminded of just how much real life fun something that looks awful on paper can actually be, and it’s an oddly perfect way to illustrate this concept. If you’re scratching your head fear not, all will be explained.

a group of people standing in an airplane

Sometimes The Cheapest Flights Are “The Worst”

Airlines usually offer their best prices on the flights which bring the most hassle. The ones that require leaving home at 4AM, get in late, or involve taking connection(s) all over the place, rather than the direct flights.

You get it, you’ve probably been on a few.

I’m here to say that if options in your budget are looking dreadful, or you hate taking back to back long flights, look for even more dreadful options. Hear me out, I’ll explain.

Make Bad Flights “Worse” To Make Them better

I was helping someone look for flights between the East Coast USA and South Africa recently and the prices for their dates were extortionate. All the memes about never recovering financially from this apply.

Anyway, it got to a point where the only remotely palatable options involved over 30 hours of travel, with not one, but two connections. Sounds awful, I know. But, when I parsed through the options, there was one I insisted they book.

In my opinion, it would actually add joy and discovery to their trip.

Two connections with say 4 hours at each point would be awful, particularly when two of the flights are over 7 hours long, but this wasn’t that. This was maximizing 23:59 in a fun and cost efficient way allowing them to explore another city.

a city with many buildings

23:59 A Recap

To recap, 23:59 is the rule that airlines can charge you extra for a “stopover” if your connection in a city between flights is more than 24 hours, but under 24 hours it’s just a connection.

Yep, even though that means you could arrive at 12:01 on a Friday and not leave until 12:00 noon on a Saturday, with plenty of time for lunch, dinner, drinks, a lil’ shopping, a stroll and whatever else, it’s just a connection. No extra charge.

Pick a great connecting city and voila.

The itinerary I found meant leaving the East Coast of the US around 7PM, landing at the first connection in Brussels about 8AM local time. The next connection? Not until 8PM.

In a small, charming European city such as Brussels, that’s more than enough time to leave the airport, see the many sights, have a fantastic lunch, maybe hit a wine bar or continue to stroll the city, shop and make memories. After all that, it’s just a short ride back for the evening flight.

For budget conscious travelers, this itinerary also avoided the need for an overnight hotel. For people more interested in the fun of a side trip, finding an overnight can make things even more exciting.

For this trip, The next onward connection was just a short hop before the long haul down to South Africa the same evening. In reality, this “horrendous” itinerary broke up what would have been a really long trip if it were just one short connection in between two long flights.

a white airplane in the sky

Some Airlines Lean Into This

Did you know that Emirates recently offered a “mile a minute” campaign with Dubai, which awarded a mile for every minute spent in the city en route to other destinations?

Airlines have learned to lean into championing their hub cities, and depending on who you fly with, you can turn bad connections into Gold. Some even offer free hotels for those looking for an extended stopover.

If you’ve always wanted to see Portugal, TAP Portugal offers the opportunity to spend up to 5 days in either Lisbon, or Porto, Portugal en route to your final destination with no additional fare. The carrier wants people to break up their trip and enjoy Portugal.

The list goes on, from Iberia in Madrid to Qatar in Doha and Air Canada in Toronto. In Africa, Ethiopian has gotten in on the mix, and Singapore Airlines offers some exclusive perks in Singapore too.

When Searches Give You Bad Itineraries

When flight searches yield bad options, the advice here is to look for the worst.

It may not be the one you want, but sometimes turning a connection into one long enough for a day trip — or side trip — is better than some of the more expensive flights with shorter connections.

Many of my best “pure travel gold” memories have been times spent en route to my final destination. Whether it’s a Michelin starred lunch or a chance to connect with an old friend, if you find a long enough connection, you can turn it to your advantage.

Flight are insanely pricey right now and hitting near record figures for summer travel, so it might be time to take this into consideration. Whether you’re looking for a bargain or just want to break up a couple long flights, it can make a lot of sense.

Gilbert Ott

Gilbert Ott is an ever curious traveler and one of the world's leading travel experts. His adventures take him all over the globe, often spanning over 200,000 miles a year and his travel exploits are regularly...

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  1. This sounds like how to turn a bad trip into a potential nightmare trip. I just came back from a flight that had me at an 18 hour layover in London. Maybe it’s just a bad example of a city, but even with 18 hours I still cut it far to close to make my connecting flight.

    Admittedly, I did have to change airports but between the customs entering the UK from the EU (thanks a lot Brexit), travel to the other airport, the covid checks and customs for leaving the UK then getting to my gate, I didn’t even have time enough to see anything. 18 hours was barely enough.

    Other cities this might work but not London!

    1. Dominic. That’s one way to think. I’ve got lots of questions here.

      So first, it typically takes under an hour by any means of transport to get from Heathrow into Central London. Second, onward connections from Victoria to Gatwick (particularly Gatwick Express) are well under an hour. Non express trains are also 50 mins. Private cars, about an hour and 10.

      Second, there are no “customs checks” leaving the UK. Those were dropped about 8 years ago. Not trying to be too critical, but I see a maximum of 4 hours (with immigration queues) to get between the two. With 18 hours, I would’ve thought you could see most central areas and fit in two meals.

      This may be helpful for future trips.

  2. I used this to my advantage on a trip from Miami to Uganda. Short flight to Atlanta (which I’m sure is required by law). Layover in Atlanta wasn’t long enough to go into the city, but the international terminal carrier lounge was quite comfortable. Long flight to Schipol with a 23:45 hours layover that turned into 24:45 hours due to time change. Hopped the train into Amsterdam and spent the day, got some sleep at a hotel next to the airport and caught my 9AM long flight to Rwanda with a 40 minute layover (no plane change) before the short flight to Entebbe. Wish I’d had some time in Rwanda, but I did get a free full day in Amsterdam.

    1. Gatwick express has been running in place of Southern fail throughout their epic issues. Not sure about pandemic or when this person travelled. What do ypu do with luggage, leave with airline to deal with? I’ve ñever considered a long layover, great article. Sounds right up my street!

  3. Don’t know if they exist anymore, but airlines used to give free overnight hotel stays for some connections via their hubs. Used it twice with KLM on a RTW where the 2nd half of the trip was nearly a year later and the booking staff didn’t know about the offer until I highlighted it to them.

    JAL and ANA used offer hotels to or from Australia if your connecting flight was the next day.

  4. Nice article. I like the idea but is it only really possible if you’re travelling light rather than with lots of luggage? When we’ve travelled long haul to Far East ex EU rather than LHR and saved a fortune in the process, we’ve always spent at least a day or two in the departure city on route, effectively getting two holidays in one.

  5. Copa has been doing this for some time now. All their flights go thru Panama City & they have deals & even a special button to engage this option when making flight reservations. Plus, in my experiences w/ them, Copa is a good airline w/ terrific employees.

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