How to Think Outside the Box for Travel Solutions

There are two kinds of travelers. First, there are those who see it all one way and give up at the first sign of a problem. These are often the same people who complain later about how their plans didn’t work out. They also do not travel much.

And then there are those who have a can-do attitude, always plan to keep moving forward, and find a way. These people are sometimes creative types, sometimes logical types, sometimes easy-going, sometimes Type-A do-ers in the extreme. Anyone can be this kind of traveler if they want to be. Here’s how!

Know Your Options and Keep Them Open

It’s always good to have options! But first, you need to know what they are. Whatever your plans are, whether that’s flying, driving, taking a train, etc., think about what your plan B would be if something unexpected happens. Do you have the flexibility to fly the next day if your flight is cancelled? Can you take the train instead? Could you rent a car and drive instead of fly if you needed to?

Or if your hotel ends up not being what it promised, can you stay somewhere else? Can you go home if it’s bad enough? Can you get your money back? Is there another option that would be better for you?

Always remember that where there’s a will, there is definitely a way! Think about what your options are, what you want your options to be, and how to make it work, whatever it is. You can do it!

There is always more than one way to accomplish anything!
Also a fun read: The WORST Travel Advice You Should Never Follow

Don’t Get Stuck Trying to Force One Thing

This is the exact opposite of “Thinking outside the box.” Do not get so tied up in trying to make the “right” thing happen that you miss the next right thing–and perhaps the only thing that will actually work. For instance, if you want to fly to Lisbon, but the price is just too high, look at connections. Look at taking a long layover on the way. Look into other ways to get there.

As an example, my husband and I wanted to visit Lisbon, but before we could book our tickets, the price doubled! We found a pretty great outside the box solution, however. It was far less expensive to fly to Madrid, spend a few days there, take a separate flight to Lisbon, spend a few days there, and fly home. We got to see Lisbon, plus take a longer trip and visit another city in the meantime!

You will have a better time (and do more things!) if you can be flexible!
Read next: 5 Ways to Bounce Back from a Bad Trip

Use ALL of Your Resources

Here’s the scenario: Your flight is cancelled, or perhaps you missed your connection. Should you call and wait on hold for half an hour? Or should you stand in line at customer service? Or should you instead try to re-book on the airline’s app?

The correct answer is: All three at the same time.

Yeah, you’ll be waiting on hold on the phone in most (but not all) cases. But you might get through before the in-person customer service agents can help the 100 other customers who also need help (you can always get out of line if the person on the phone takes care of your problem). Or, you might get to the customer service agent first (you can always hang up the phone if you’re still on hold). Or, you might be able to re-book quickly and easily on the airline’s app (or you’ll get an error message and it won’t help at all).

The point it, try everything! It costs you nothing to try all three at once. Apply this principle to non-airline situations as well. Get creative!

If you want the next best flight after a cancellation, use all your resources to make it happen!
Related: The Ultimate WORST Time Wasters on Travel

Consider a Different Method of Travel

Planned to fly, but your flight is cancelled? See about taking a train. Or, perhaps, can you rent a car and drive? Is there a ferry? Where there’s a will, there’s a way! Okay, maybe not every time (there are some destinations that can only be reached by plane), but usually, in a pinch, you can find a different way if you truly need to.

For instance, back when the United States still required testing to enter the country during the pandemic, we took my mom to Canada. We ended up not needing a plan B, but we had one. If any of us had tested positive, we would have rented a car in Toronto, driven across the border to Buffalo, NY, and flown home from there. Because driving across the border was allowed without proof of a negative test, this would have been the best option if we needed it. Thank goodness we didn’t need it, though!

We got to have an stress-free time in St. John’s, Newfoundland, because we knew we could get home successfully in a bad situation!
More here: The Top 10 Ways to Ruin Any Trip


When you know that there must be a better way, there usually is. And it’s usually whatever the locals are doing! When we wanted to get the famous Pasteis de Belem in Belem, Portugal, we thought standing in the long, long, long line was the only way. But I’m so glad I decided to ask someone if that was the right line, because there were actually three lines: One for sit-down service, a second for order ahead pick-ups, and a third to grab a pastry to go. That last one was the one we needed–and the shortest line!

This goes for lots of different situations on travel. Ask the customer service agent if there’s a better way to get to your destination. Ask at the hotel for the best running route rather than winging it on your own. Ask your server what the most authentic item is on the menu. It might not be what you expect!

When you think there must be a better way, ask the locals!
Keep reading: The Best Advice for New Travelers

Hang Up (Politely) and Call Back 

Once you’ve traveled regularly for a while, stayed loyal to an airline or hotel or rental car brand through a few program changes, and learned by experience (AKA: Trial by Fire), you’ll pick up a few things along the way. You’ll learn the intricacies of how it all works. You’ll learn the little catches and the strategies businesses use to make sure they make a profit while you think you’re getting a deal. You’ll learn the ins and outs of “the system.”

And then, you’ll realize you actually know more than the customer service representative on the other end of the line! This is a confidence booster. But it’s also a source of frustration. You know what you’re allowed to do. You know what the rules are. You’ve read the latest terms and conditions of the new loyalty program. But the person who can do something about it for you says “No.”

The solution: Say, “Okay. Thank you! Have a nice day!” And then hang up and call back. Unless you are calling a particular office, you will 99% for sure talk to someone else, someone who might also know what you know. Someone who might be willing to go that extra mile and look up the rule you’ve been quoting to them. Someone who might pass you on to a supervisor instead of simply telling you that you can’t do that.

Be nice, though! Customer service representatives can sometimes write notes about you in your electronic file, and the next person you speak to will have a preconceived notion that you’re “difficult” if the person you spoke with before says you were. Be kind, hang up, call back!

When you know you’re right and you earned that upgrade, don’t give up just because the agent says “No!”
Read on: How to Be Your Own Travel Advocate

Want more? Get all my best travel advice on my dedicated Travel Tips Page!

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Published by quickwhittravel

Welcome to the blog! We do things a little differently around here: no ads, no negativity, and no checked luggage, y'all. My name is Whitney, and Quick Whit Travel Blog is your one-stop shop for all the best travel tips, packing advice, and destination information. Click around or message me on social media @quickwhittravel for more!

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