Looking for a Travel Companion? the Best Questions to Ask Before Your Next Trip

Excited about planning your next big trip, but terrified of choosing the wrong travel companion who could turn your dream vacation into a nightmare?

The biggest fears keeping you up at night are:

What if you end up stuck with someone who complains about everything, has completely different priorities, or expects you to plan everything while they contribute nothing?

How do you have those awkward conversations about budgets and expectations without seeming controlling or judgmental?

And if you’ve never traveled with someone before, how do you predict whether they’ll be a supportive partner or a high-maintenance burden who makes every day stressful?

Having experienced both travel companion disasters that made trips miserable and finding my ideal travel buddy through the Bumble BFF app, who’s turned international adventures into pure magic, plus learning from family trips, I’ve identified the exact questions and compatibility factors that predict successful vs. disastrous travel partnerships.

The difference wasn’t luck—it was learning to identify crucial compatibility factors like planning styles (I’m a planner who’s open to spontaneity, not someone who wings entire trips), schedule alignment (discovering someone cancels all your restaurant reservations without warning), and communication skills that turn crises into manageable adventures.

This comprehensive guide is perfect for first-time group travelers nervous about choosing companions, solo travelers considering the leap to shared adventures, and anyone who’s experienced travel companion nightmares and wants to avoid repeating those costly mistakes.

From my travel buddy patiently waiting while I panicked on Italian stairs to finding alternatives when a $500 ice breaker cruise was way outside my price range, I’ve learned that the right travel companion transforms challenges into stories you’ll laugh about for years—which is why I’m sharing every hard-learned lesson and practical question to help you find that magical travel chemistry.

Do You Have Compatible Travel Styles?

Planners vs. Spontaneous

Much like the debate between the words ‘traveler’ and ‘tourist,’ some people are ‘planners’ and some people are ‘spontaneous.’

If it’s not especially clear on this blog, I’m very much a planner. But I am open to spontaneity.

That means if we find some cool festival, event, etc., while on the trip, I’m open to tossing aside the plans for that night.

Some people are very rigid and like to know what they are doing at all times. I am occasionally like this dependent on the situation.

Then there are people who go on a trip without a single plan.

I… cannot do this. The thought of spending hundreds on a flight and far more on a hotel or hostel to then wing a trip is not within my traveler DNA.

No matter which you are is fine. No judgment, but find out which your travel companion is, as getting ahead of this will help alleviate a lot of issues.

Communicate the Level of Effort

I recently went on a trip where I very clearly stated I was a planner, but that I don’t like to plan it all as I like trips to be a collaboration. The companion agreed to book reservations for our meals as we were traveling over the holidays.

They then went on to cancel all of our reservations during the trip for a variety of reasons—didn’t like the set menu, didn’t know it was a continental breakfast, etc. All things they could have figured out ahead of time, hence the planning.

This annoyed the bejesus out of me as I felt the effort they said they’d put into the trip just wasn’t there.

They also didn’t communicate the cancellations until I said something like, “Oh, we have to be at X restaurant at 1 p.m., right?”

They’d then respond, “Oh no, we canceled that.” So, communication was also severely lacking.

Had instead this person said, “I’m not much of a planner, can we just find places while there to eat.” I would have said, “Sure.”

But then the caveat would be, just know it’s a holiday, and it may take some time to find a good place to eat. As long as we were all on board with this, it would have been fine!

Is There Budget Compatibility?

Having budget incompatibility can really make a trip awkward!

This is one of the first conversations my travel buddy and I had before venturing off to Italy.

Because it’s kind of rude to be like, “Hey! How much do you make?” We instead talked about accommodations.

The price range of a hotel or hostel your travel companion is okay spending on will tell you a lot.

If they’re dying to stay at the Ritz—they’re bougie.

If they’re frequently hostel hopping—they like to be on a budget.

Of course, there are some exceptions to these generalizations. Some people have the money but enjoy the community of a hostel, for example. But their preference of price range will still tell you a lot.

How to Be Negotiable

A good travel companion will also be negotiable.

For instance, my travel buddy wanted to go on an ice breaker cruise with ice floating while we were in Rovaniemi, Finland. It was $500 per person.

That sounded bananas to me, as it was more than I was spending on the flight to Finland.

So, instead of being like, “You’re crazy,” I found an alternative. A northern lights tour with ice floating for around $100.

She agreed, and it wound up being the first time we saw the northern lights on that trip was on that tour.

Now, she could have turned me down as well. And at that point, I would have just accepted that she was going to go on the ice breaker tour without me and I would have entertained myself for that day.

Splitwise

If you’re looking for a way to easily track expenses so everyone pays their fair share? I highly suggest Splitwise.

It makes entering expenses, tracking them, and settling up at the end of a trip so simple!

It’s a free application, though you can pay for some extra features if needed.

All you need to do is create a “Group” to which you’ll add your travel companion.

Then, throughout the trip, you can add costs such as gas, drinks, Uber/Lyft, etc., to that Group. It then shows a running total and calculates who owes what to whom.

I’ve used it on my international travels, and it was super simple to enter in differing currencies, so no worries if you need to enter British Pounds, then Euros, then USD, etc.

The only caveat about varying currencies is that I had to pay and upgrade to Pro to convert it, but it wasn’t much. Or you can do the calculations yourself.

Shared Interests vs. Independence

One of the big things that I think makes my travel buddy and I’s trips work is that we are very good about communicating our shared interests and our differences.

She loves a long, arduous hike, while I love wandering around a museum with an audioguide to my ear.

But we both know this about each other, so when one of us says, “Hey, I want to do X,” the other isn’t offended if we do it without them.

The only thing I ever ask of her if she’s going off to hike the Dolomites for the day or some other mountainous place is to tell me when I should expect her back.

This is simply so I know she’s safe. I don’t want her 127 Hours‘ing!

If she says she’ll be back at 7 pm and it’s past that and she hasn’t communicated the train or whatever is late, I know to get worried. Aside from that, I tell her to have fun and I’ll see her later.

Conversely, I’ll ask her, do you want to go to this museum? And sometimes, she’ll pass. I then know while she’s hiking that it’s something I can do on my own.

Communication and Crisis Management Skills

This independence only works because we have good communication. We are very clear, but also respectful.

I never say anything negative about her doing her thing. She loves it. It’s very clear by the massive amount of nature on her account.

Conversely, she does not mock me when I take her to Marco Polo’s house in Venice or ramble on about the Medici in Florence.

Even more importantly, she is not impatient with me.

For example, when we were climbing down the dome of the Cathedral of Santa Maria del Fiore in Florence, it was a very weird climb because the stairs were shaped like the dome, so you kind of looked like you were walking up while actually walking down.

She could have gotten annoyed with me clutching onto the railing for dear life and taking a longgggg time, but she didn’t.

I also got a bit panicked on my way from Naples to the Amalfi, where we met up later in our trip.

I had gotten the wrong bus schedule and had to wait hours for the next one. Then, when I got on the bus, their app/site wouldn’t accept my credit card, and if I recall, they didn’t take cash.

Luckily, the bus drive took pity on me and waved me on.

I then nearly died going down the stairs in Positano so by the time I met up with her I felt like I wreck. She meanwhile, cool as a cucumber. Told me everything was fine and it all worked out.

Moral of the story—have patience, empathy, and adaptability.

Sharing Concerns and Issues

It’s also important to communicate potential concerns and issues.

If you or your travel companion get sea sick and you’re planning on going a boat tour, speak up!

No one will know unless you say something, and the sooner the better!

Same goes for things like dietary restrictions, food preferences, and yes even things like your ability to ride a bike.

Secrets out! I cannot ride a bike ‘well’ so this was something I’ve discussed prior to trips.

Do You Share Daily Rhythms and Habits?

One of the harder things to suss out before a trip is daily rhythms.

On a regular day, I’m a night owl, up till the wee hours.

On a trip, I’m up at whatever time you need me. 5am! Sure thing!

My travel buddy conversely is usually a morning person, at home or on vacay.

While the ‘at home’ habit is fine either way, the ‘on vacation’ one can make life difficult.

While traveling with my family to Greece, I found out I am the early bird and they are the midmorning bird.

I’d be up and ready to see the sights by 8 or 9am and they’d be ready to leave the hotel by… noon. My god how this annoyed me. That’s half the day!

Mind you, I was the only one doing full hair and makeup too!

A few days into trip I had to have a conversation with them and be real clear what ‘leave the hotel by X time’ was as I didn’t want to burn any more daylight!

If you are traveling with someone who’s working remotely, have that conversation as well.

Sometimes my travel buddy is working and needs time to have a work call or Zoom. I make sure to keep quiet during the time or find something else to do to respect her work schedule.

I recently when on a trip where I very clearly stated there’d be times I had to work. Unfortunately, my travel companions made me feel awkward about it which didn’t enliven the trip any.

Should You Do a Trial Run Before a Big Trip?

Doing a short trial run can help you determine if you can stand your travel companion for longer periods of time.

My travel buddy and I dived right into a 2 week trip, which could have gone horribly wrong, but luckily didn’t.

In hindsight, I’d highly recommend the short ‘test’ trip to make sure you can handle more than 24 hours together.

Red Flags to Watch For

During a test trip some red flag behaviors that might indicate future problems you can look out for are:

• Are they mean to the waiter?
• Are they short with the tour guide?
• Are they looking for something to complain about? (too bright, too noisy, too dusty, etc.)
• Do they communicate clearly or are you pulling teeth?
• Are they really thrown off when something goes awry?
• Are they barely putting in any effort? (especially if they’ve promised to)
• Are they always worried about money? Or want to spend more than you’re comfortable with?
• Do you not have any shared interests?
• Are they afraid to be alone?
• Are you on opposite schedules?

Questions to Ask a Perspective Travel Companion

Based on how well my travel buddy and I work, versus how it’s worked out with others, I’ve created some questions to ask before you pick your next travel companion.

I believe they’ll help give you some insight even if you don’t wind up doing a short trial run trip.

1. What countries are you looking to visit?
2. What are you excited to do there?
3. Are you more of a city slicker or nature lover?
4. What are your pet peeves?
5. Have you traveled solo before?
6. Have you lived alone before?

Questions 1 and 2 tell you are you excited about the same or similar places, as well as activities. If someone said to me, I want to go to Milan just to shop. I would not be going with that person as I don’t really enjoy shopping. But if they said, I want to do to Milan to see Da Vinci’s Last Supper, sign me up!

Question 3 tells you how active the person is and how willing they are to do things outdoors. I’m not a big nature lover, but I can appreciate some, so I’m kind of in between but definitely lean more toward city.

Question 4 will tell you if this person has something that’ll annoy you. For instance, I hate when people chew with their mouth open. If my travel companion responds with, “oh yeah, my Grandma yells at me for doing that all the time.” Well, now you know.

Question 5 and 6 tells you how independent someone is. I’ve met people who couldn’t even be alone for a single second. That drives me nuts! I’ve lived alone in the past and also traveled alone so if you want a day alone, that’s a-okay with me. I don’t want someone glued to my side for a week that I feel like I need to take care of.

It’ll also tell you how street wise or how much common sense they have. I’ve found people who can be alone are far more self-reliant and thus will have some common sense while out and about.

Final Thoughts on What to Look for in a Travel Companion

All this to say. Not every moment will be perfect. I’m sure I annoyed the heck out of my travel buddy when I was complaining how cold I was in Rovaniemi. But I apologized if I was annoying and we moved forward.

The reverse has happened as well.

What you can focus on is finding someone who is flexible, communicative, puts in effort, negotiable, shares some interests, patient, empathic, and adaptable.

Related Travel Planning Guides

• How to Plan an International Trip on a Budget: My Step-by-Step Guide
• How to Use Google Maps to Plan a Trip in 9 Simple Steps
• 44 Things to Do Before Traveling Internationally + My Free Pre-Trip Checklist
• Looking for a Travel Companion? Best Questions to Ask Before Your Next Trip
• Viator vs. GetYourGuide: Which Is Better for Booking Tours? An Honest Review

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