Want To Ruin Your Friendship? Travel Without Asking These 13 Questions

Traveling With Your Bestie

Unless you’ve found your travel tribe, finding a friend with a passport can be more challenging than the Paleo Diet.

So when a pal agrees to a trip and they actually pay for the ticket, it makes your heart flutter with thoughts of mountain-trekking, city-hopping, and beach lounging.

But consider this: who you travel with determines if your trip will be one for the history books or a gripe session on Facebook.

It’s pretty to think any of your friends would make the ideal travel sidekick. Truth is, that travel – just like living together – exposes a lot about a person.

Check Travel Resumes

Before you go gallivanting with someone who’ll make your trip an episode of The Real World, ask them these thirteen questions.

If you have a candid discussion on every question, you’ll save a friendship, even if it means you won’t travel together.
1. What is the Most Challenging Place You’ve Ever Traveled?

If you’ve solo traveled across Thailand, twice about someone whose was challenged in a city like Toronto.

Those with less travel experience get stressed at situations that frequent travelers breeze through. They also need more motivation to stretch their comfort zones. Not to say that your friend wouldn’t be up to a challenge.

Some people lean into hard situations while others bolt.

The key is knowing which type of person you’re traveling with.

2. How Do You Pack?

Will they bring three suitcases – one of which you’ll end up dragging?

If you read this blog regularly, you haven’t missed the importance of traveling light. You’ll want a travel partner that understands that. Maneuvering an airport and getting through a city is much easier and cheaper with less luggage.

What’s in a person’s suitcase also says bunches about who they are as a person.

Pack Light

Don’t expect someone with a huge suitcase for a weekend trip to be the type to rough it through a cave hike. Packing a separate suitcase just for stilettos is a telltale sign that they aren’t exploring off the beaten path.

3. What is the Best Hostel You’ve Stayed In?

Know upfront if your travel mate can stay in a hostel or if they need a room with a minibar and poolside view.

To travel more often, learning to stay in low-priced lodging boosts the number of trips you take yearly. It’s okay to splurge every once in a while, but if your travel partner isn’t up to the challenge, they probably won’t be your go-to.

4. How Do You Spend Your Day?

If you’re up early and running out of the door with a full day’s itinerary, we couldn’t travel together.

Ask your travel partner how they prefer to spend their days. Some of us like to sleep past sunrise and take our time getting dressed.

You’ll have seen half of the city by the time we’re ready to leave the room. Save yourself a headache and look elsewhere for a travel partner.

“Friendship … is born at the moment when one man says to another “What! You too? I thought that no one but myself . . .”       ~ C.S. Lewis
5. How Much Spending Money Do You Travel With?

Knowing your friend’s spending style helps you both figure out what activities to plan. It also gives you a good idea of their expectations for the trip.

I’ve heard horror stories of travelers who vacationed with someone who ran out of money halfway through the trip and had to bum off of others.

Discuss a general budget before agreeing to travel together so that everyone’s bank account will be happy.

Travel The World

6. What Activities Do You Enjoy?

If you are an adventure traveler and want to wrestle crocs, make sure your travel pal is up to the challenge. Don’t let your friends trip turn into a solo trip because the two of you have different interests.

I made the mistake of traveling with a shopper and we spent half a day in the mall. It was the worst time I’ve ever spent on a trip. Figure out early on how a new travel pal likes to spend their time to keep you from wasting yours.

Awe Inclusive travelers have more fun because they open themselves to more opportunities. Anyone traveling with you needs a similar mindset.

7. What is the Most Stressful Travel Situation You’ve Ever Encountered?

Question seven is different from the most challenging place you’ve ever visited. This question explores stressful types of situations.

Even though traveling offers some of the best fun money can buy, it also offers unforgettable lessons.

Travel Is The Best Way To Learn

I’ve been around travelers who are cool as a cucumber in harrowing situations, while others have gone bat-shit crazy at the slightest inconvenience.

Which type of person are you considering traveling with? It doesn’t take many temper tantrums to ruin a great vacation.

8. Are You a Picky Eater?

Looks don’t matter; if it smells good, I’ll try a bite. If it tastes okay, I’ll take another bite.

I grew up in a “don’t leave the table until your food is gone” household. Stuffing food down until my plate is cleared is no problem. I’ve found that everyone isn’t as haphazard about what they eat.

The person applying to be your new travel partner should have similar food needs as you.

Can they eat street food? Are they adventurous enough to order from a menu they can’t read?

There are picky eaters who’ll make visiting any restaurant a challenge. Be just as picky when choosing a travel buddy.

9. Do You Prefer a Planned Day or Going With the Flow?

I despise alarm clocks. Luckily (or maybe not so much by luck), my job allows lots of flexibility. Most days I don’t need an alarm clock.

This doesn’t change when I’m traveling. I prefer waking up when rested to flexible plans for the day.

Unless you plan to spend a lot of time apart doing your own thing, it might be nice to travel with someone who shares your views on time management.

10. How Do You Want to Treat Yourself?

What’s your splurge?

I don’t spend much on food, lodging or activities when I’m traveling. But I have no problem dropping a stack or two on an amazing souvenir or experience. I spoil myself with unique or one-of-a-kind items.


What does your future travel comrade consider a treat? What is a big ticket item that they’d like to buy or do?

In my travel planning guide, I suggest letting a friend choose an activity for you to try when you travel. This stretches your comfort zone and helps you experience something you hadn’t considered.

It’s perfect to learn more about each other, try something new, and create lasting memories.

11. Partying or Naw?

Partying in another country is an unforgettable experience for so many reasons.

As friends, you’ve likely partied together a lot. Club hopping in exotic lands takes this pastime to the next level. Make sure your friend is comfortable partying in a new place.

Things to consider: how strong is their intuition? How do they behave when they’re drunk? Could you count on them in an emergency or if you were drunk?

If your friend isn’t comfortable handling a ridiculous, drunken situation in another country, your trip should involve a more civilized form of partying.

“It is one of the blessings of old friends that you can afford to be stupid with them.” ~ Ralph Waldo Emerson
12. Can You Handle a Day On Your Own?

Solo travel is one of the most liberating travel experiences. It frees you up to explore new places, people, and events on your own time and in your own way.

The next best thing is creating solo time when you’re traveling with others.

Are they okay splitting up? How will your friend handle time alone? Would they be okay if you found new friends to hang out with or would they totally freak out?

Letting your friend know your plan helps them prepare for when you break away from your twosome.

13. Are You Okay With Buying Travel Insurance?

We all plan for the best, but no one wants to deal with an emergency abroad without travel insurance.

I traveled with a friend who got ill halfway through the trip. He ran a fever and lost his appetite and felt horrible. Knowing we had travel insurance made everything better.

If we had to fly home early, our travel insurance would have covered it. That kept my panic at bay during the entire endeavor. If you’re injured or worse, travel insurance makes next steps easier for you and your family.

While these questions will ultimately help you decide if your friend is the right person to travel with, sharing stories has another positive effect.

Storytelling is one of the best ways to connect with someone.

Asking the right questions and relating similar experiences helps strengthen a relationship. And this is necessary if you’re planning a trip together.

Traveling has a way of solidifying friends or creating enemies. Plan accordingly.

Do you agree that you can’t travel with everyone? Let us know in the comments!

Questions To Ask Before Traveling With A Friend