Turning “Horrendous” Flight Itineraries Into Pure Travel Gold

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.

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.

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.

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.