Key Questions to Ask Before Traveling With Friends

We travel a lot. While it’s usually just the two of us, we have a number of friends who will join us on the road from time to time. After moving abroad, that time with friends here, there, and everywhere only increased.

It turns out people want to visit you when you live somewhere amazing.

At this point, we know which friends are compatible with our travel style. We know which friends are reliable when plans are made, and which are more likely to flake.

This is essential information to have before you spend that hard-earned cheddar on that bucket list trip. These questions to ask before traveling with friends are a good way to get a sense of what you’re dealing with, especially if these are new pals in your orbit.

Where do you want to go?

This one should feel simple, but it really isn’t.

If you have a lengthy bucket list of destinations in your travel brain that you never deviate from, that can leave little room for your friends’ hopes and dreams. It can also leave little room for good deals that come into your inbox.

I tend to want to do all of the things at all times, so if you’re headed somewhere that sounds remotely fun, I’ll likely want to latch onto that plan.

The only exception may be if I’ve been somewhere a dozen times…unless it’s the Wisconsin Dells or somewhere of similar high caliber.

What’s your booking style like?

I’ve completely embraced choosing destinations based on hot deals. That doesn’t mean I’m completely against booking a trip because one of my friends really wants to go on that trip.

I don’t love last-minute travel, though, unless it’s on one of those aforementioned deals. If you don’t plan ahead, you’re more likely paying more than you should for that trip, especially if you’re traveling in the summer months.

If you can’t agree to basics like how you’ll book that trip and when, your travel styles may not be compatible.

What’s your travel style?

If you live in a constant state of FOMO and your travel partner just wants to kick it at a local coffee shop for the duration of your stay, it’s going to be a frustrating trip.

You’ll be cranky about missing out on whatever bucket list experience you’re missing out on, and they’ll be cranky because they’re tired from trying to keep up with you.

I’m all about enjoying the local caffeine, but I tend to fall into the camp of doing what I can with the time that I’ve got. I’ve calmed down quite a bit lately, but I’m just not going to laze around too much, perusing the local Netflix.

What’s your idea of the perfect vacation?

Along those lines, get to know the kinds of things that get your friends’ motors running when it comes to planning travel.

When I’m touring somewhere new, there are rest breaks in there for cheese and wine. If a thing isn’t super unique to the destination I’m in, I’m going to want to move on fairly quickly.

This means shopping is limited to local wares, not explorations of international versions of American chains, so Red Lobster, be gone with you.

Note: If you come across a travel blog that recommends Red Lobster as a must-stop no matter where you’re at, run. It’s never a must-stop. I promise.

Anyway, here’s a tip if you’re not sure whether you’ve signed on to a potential disaster, especially with new friends wanting to plan a trip with you. Take a little test run with your potential travel partner with a local day trip somewhere.

You’ll know what you’re dealing with fairly quickly. 

What’s your budget?

This can come down to a daily budget or a total budget. I’m in the mid-range travel camp. I’ll share a room if absolutely necessary or in a city where rooms cost many dollars and I want to save money.

I typically prefer my own space if we’re talking about a longer vacay, though, whether that’s in a hotel or something more condo-like. I’m generally not down with hostels.

Even if you arrange your own lodging, if you’re traveling with someone who wants to blow their budget on an executive suite, it’s going to get awkward quickly.

They’ll be talking about their private jacuzzi jets and room service at breakfast while you’ll be there thinking about how you were bumping elbows while brushing your teeth.

The expenses don’t end there.

You’ll need to nail down the tours or excursions you’re all into, transportation costs, and a food budget.

Is there anything that would cause you to deviate from your budget?

I’m not saying you should all return broke from travel abroad, but if there’s something one person in your travel group is likely to splurge on, it’s a good thing to know.

That could affect your own budget, especially if you have a hard time saying “no” when decisions are being made quickly.

Are you invested in visiting international McDonald’s locations?

Your travel partners may not need to eat at every restaurant featured on Chef’s Table. Conversely, they may be into daily visits to the international McDonald’s.

I really don’t want to give the McDonald’s corporation much of my money domestically, so am even less likely to do so abroad. If you’re only comfortable at chain restaurants and fast food joints, we wouldn’t be good travel buddies.

I need to travel with folks who want to try the local cuisine or at least local takes on ethnic cuisine.

I’ll allow it once in a while, but if we’re going to travel together across New Zealand for a week and you want to hit up fast-food chains every night, it’s just not a good fit.

What’s your approach to food?

Are you going to invite your vegan friend on a tour of all the barbecued meats in the Carolinas?

That may be the end of that friendship, which is hopefully the outcome you were seeking if you pulled this move on someone with those dietary restrictions.

Eating the local cuisine is a huge deal for me. Despite how squeamish I may be about certain textures I’m going to try my best to try new things.

Fun fact: I’ve tried oysters, aka “the boogers of the sea,” patent pending, numerous times. It’s just not working for me, so please no recs in that direction.

On the flip side, if you’re a less adventurous eater, you’ll need to account for that. You need to make sure that your travel partners are flexible enough with you that you won’t have to hoard food from the continental breakfast every morning.

READ MORE: A food tour is an excellent way to relieve some of your travel planning and get to know a destination.

Do you bail on plans?

We all have that one friend. She’s supposedly on her way to the group dinner you’ve had planned for six weeks, and then at the last minute, she bails because she got a flat tire.

Maybe her ex-boyfriend just called her and now she’s a mess. Maybe she just got the dates mixed up. You said you were on your way, Gina!

Still, you don’t completely cut her off, because once in a blue moon, she does make it out and it’s the most fun you’ve had in a long time.

That doesn’t mean you should travel with her, though. Find a travel buddy who doesn’t add to your anxiety.

Can you imagine that girl on a large scale? If she even made her flight, you’d be dealing with her flakiness for the entire trip and you don’t have time to wait around. There are cheese plates and adventures to be had.

Are you super flexible or super rigid?

I’ve been doing some work in this area over the years, as I’m Type A to the max and have been known to wig out when I have to deviate from plans.

I’m trying to be better about things that happen that are out of my control, like having the airline misplace your luggage on back-to-back trips to the same region of the world.

What I tend to have, though, are backup plans. When I’m in that situation of “Well, what do we do now?” there’s a ready answer that’s just as good a time as the planned one.

How do you react when things go wrong?

Do you go into meltdown mode, ruining the rest of the day with your tantrum?

This requires some self-awareness, but it’s easy enough to figure out about others.

As a little test to figure out what you’re dealing with when considering travel with your pals, try switching up dinner plans with said would-be travel partner. You’ll get to see how they handle it.

If they blow up at you or resort to physical violence, international travel with them could be too much too soon.

Can you get to the airport on time?

In the most basic sense, you want to travel with people who will do things like get to the airport on time.

A Home Alone-style rush to the airport starts the trip off in a super stressful way, and that’s not what I’m about when I’m traveling.

How involved do you want to be in the planning?

I usually take on most of the planning when it comes to travel.

My travel buddies know this about me and are typically relieved that I’m taking it off of their shoulders.

This doesn’t mean that they don’t get any say in what we’re doing on our shared trip together.

I’ll typically figure out the route, and offer up options by neighborhood at our chosen destination, for efficiency’s sake. From there, my travel pals can identify their priorities and we go from there.

If you’d like to break up some of the tasks, make sure you’re going with someone who will follow through. You don’t want to get to your destination to find out an attraction is sold out because Karen forgot to get those front-of-the-line tickets.

Do we have common interests?

You hopefully know most of your friends well enough that you already know what, if any, your common interests are. You should also know whether they travel with a specific purpose in mind. 

If you don’t, you should keep in closer contact with them. Play some getting-to-know-you games or something. Peruse their Facebook if you’re still into that.

Sometimes you meet people that you feel like you’re really getting along with, and want to take that plunge and plan a trip with them. Explore what they like to do on trips they’ve taken.

People love talking about themselves and places they’ve been, so this shouldn’t be that difficult of a research task. 

How adventurous are you?

There are some people who only travel to climb mountains. 

There are some people who only travel if they’re able to bring their kids.

Others only vacation if there’s scuba diving involved. 

That’s not me, but those are important things for me to know before I’m going to decide whether you’re a compatible travel buddy for me.

I’m not a climber, although I love a good hiking trip, and I do quite a few things that are not child-friendly. (We’ve traveled with our friends’ kids, by the way. It just requires a different level of planning!) I’ve been diving, but do I want to do it on every single trip?

Nope.

READ MORE: Sometimes things get very adventurous. Check out my detailed review of a super scary hike at Rocky Mountain National Park.

What friendship qualities do you bring to the table?

You want travel friends who pay you what they owe you if you’re taking turns sharing costs. You want friends who bring what they need with them so you’re not spending a bunch of time abroad buying bathing suits for Karen.

In this scenario, Karen forgot to bring one on your Caribbean cruise.

Note: I’ve never been on a cruise nor have any interest in going on a cruise. This was obviously just a bad example.

Friends with a good sense of direction, even in a brand-new place, are good to keep around, too. This is especially true when you’re planning a road trip with friends.

Do we have to do everything together?

I don’t even have to do everything with Brian when we’re traveling. He likes to golf. I don’t. It’s a good time for us to spend some time apart pursuing our own interests.

This is a good one to consider especially if it’s not the first time you’re visiting a place. You may not want to drop a bunch of cash on an activity that you’ve already done. If your friend has never done that thing, they may want to prioritize that activity.

That’s the perfect time to go your separate ways and do the solo travel thing for the afternoon. It’ll be OK.

If your friend is a nervous traveler, though, they may not want any time away from you. It’s important to discuss beforehand.

Do you have any major pet peeves?

I’m sure I have some annoying quirks that I haven’t even identified yet. I know my own list of pet peeves in others is probably too long.

A big one for me is efficiency in travel. I don’t like spending hours on public transit to return to the same place I was at yesterday because my friend forgot they wanted to see this or that. If this feels specific it’s because it is.

If you’re a more laidback individual who likes to while away the afternoons at distant cafes, we’re just not a great fit.

I can also be fairly introverted. My best friends are all comfortable with an easy silence. We don’t need to chat for the duration of our flight because that’s when we can catch up on our stories.

Do you get hangry?

Hanger is real. I know that Brian needs regular meals and snacks throughout the day if he’s going to be in a decent mood during travel.

Add jet lag into the mix and things can get even spicier. If you know you’ll need to eat at regular intervals, let your friends know so that can be a part of your planning process.

What’s your transportation style?

You may not want to plan a road trip with someone who doesn’t even have a driver’s license. You may not want to plan a European vacation with someone who has an aversion to public transportation.

Have you been on their trains, though? They’re awesome.

Before booking a trip, have a sense of what your friends expect as far as how you’ll be getting from Point A to Point B. This may come down to budget, too. I wouldn’t sign off on a trip that involved black limousine service to and from each stop.

Are you cool with other cultures?

Do your due diligence as to whether your potential travel partner is a closet dirtbag.

Do they make frequent comments about how disturbed they are by how not everyone knows English? A trip to a remote corner of the world may not be the best bet for them unless they’re footing the bill. (I kid.)

Do they make awkward faces whenever presented with a cuisine they’re not familiar with?

Are they judgemental about food when it’s different from what they’re used to, or constantly comparing everything they and eat to “how it’s done at home?”

Do they refuse to learn anything about the cultures, customs, or languages they’ll be experiencing?

C’mon now.

Are you open to compromise?

I’ve already told you that I have a frenetic travel style. That doesn’t mean I’m ONLY taking those kinds of trips.

I have friends who I wouldn’t necessarily take on a tour of Europe, where I’m looking to beat the previous day’s step count with all of my aggressive sightseeing.

I DO have friends that I’d take on a more relaxed trip, which I do from time to time. Those are your beach vacation friends. They like a cocktail with a little umbrella inside, and reading trashy novels on the sand or by the pool. They know this.

To compromise, they’re not opposed to a few excursions or exploration activities on a trip that’s otherwise meant for relaxation. A trip with friends doesn’t have to be all about one thing unless you’ve all agreed that’s what you’re after.

Just make sure everyone knows what they’re signing up for before booking your travel.

Are you a night owl or an early bird?

I feel like I’m at my best around midday, so I can’t really call myself either. If you’re firmly in one camp over the other, though, that’s a good thing for your potential travel buddies to know.

It can be a challenge to wake up for a morning excursion if you’re up all night. You likely don’t want to deal with someone forced to wake up after a long night out, either.

Are there any health or medical concerns to share?

I’m not telling you to violate HIPAA, but if there are things going on with your friend that will affect your travel, that’s important information to know.

This includes physical limitations, food allergies, and any medication regimens that require that you’re out of the sun, off the sauce, or in bed by a certain hour.

Do you have a sense of humor about travel?

A sense of humor goes a long way when the shit hits the fan while you’re abroad.

You can get upset and refuse to leave your hotel room because something didn’t go your way, something went wrong, or you weren’t able to do something you wanted to.

Or you can roll with it, laugh it off, and find joy in the fact that you’re all lucky enough to be traveling together in the first place.

Obviously, if something truly awful happens you can feel those feelings. If your friend turns into some monster jerk while abroad, you can call them out on it and leave them at home the next time around.

If it’s a minor thing, though, laugh about it. Embrace the moment. It’ll all make for great stories around margaritas when you’re back at home.

Is there anything you’d be uncomfortable doing?

If your travel pal is sober, you probably shouldn’t be planning a worldwide distillery tour with them. If they suffer from intrusive thoughts as I do, they may not be as adventurous as you’d like.

Talk through your non-negotiables before you book a trip so that no one is stressed out or disappointed on your trip.

Are you planning to unplug on this trip?

I’m pretty terrible about finding the right balance between work and play. If I don’t work, I don’t get paid, so I’m rarely completely unplugged from the outside world.

If my friend has the expectation that they’ll have my undivided attention for the duration of our trip, they’ll likely be disappointed if they don’t express that desire ahead of time.

If you’re traveling together without your partners, that’s something to consider, too. Are you two going to spend large chunks of time on pillow talk with loved ones at home, or will you be more present?

Are we close enough for brutal honesty?

Let’s say you’ve determined based on the tips above that the friend you’ve been thinking about bringing along on your next vacay does not meet the criteria for travel with you.

That doesn’t mean they’re never going to leave the state. 

It just means that maybe there’s someone else out there who will be a better fit for what they’re looking for, and vice versa.

It also doesn’t mean that you can’t be friends with this person. I have all kinds of friends who I don’t travel with, but I enjoy their company immensely. I also have friends whom I love dearly who just can’t travel, for a number of reasons.

Life doesn’t include travel for everyone, and I’m not going to judge you for it.

Fun fact: Yes, you can still be friends with pals that you know you wouldn’t gel with abroad or those who can’t come along on trips with you. It’ll all be OK.

Am I a good fit for your kind of travel?

Sometimes the best questions to ask before traveling with someone have more to do with you than your travel buddies.

This isn’t just about finding the perfect travel buddy for you. It’s also about finding the perfect travel buddy for them. I’m talking about those friends of yours who are shelling out quite a bit of cash to go abroad.

They want a great experience, too.

Are you a good traveler yourself? Are you a good communicator when things go wrong, and when you’re letting the group know what you envision for a trip abroad?

Are you a rigid traveler, or a flexible one? It’s important that your friends know what they’re getting themselves into if you’re the one that may be a tougher sell on them.

Prove them wrong. Be the cool, calm, collected you that I know you can be, and have the time of your life experiencing all there is to experience out there in the world.

There’s no such thing as a PERFECT travel buddy.

You and your travel companions don’t have to have everything in common. In fact, there’s really no such thing as the perfect travel buddy.

Traveling with friends becomes a good idea when you cover basic compatibility questions around budget, travel style, and expectations.

There’s always compromise involved when you’re traveling with friends, whether that’s on how much of your itinerary you get through or where you’re going to have dinner.

Differences are fine. In fact, differences are good.

You may find yourself enjoying something new that your friend heard about in their travel guides, or embracing a little more spontaneity if you’re the planner in the group.

As you think about the right questions to ask when planning a group vacation in your friend circle, consider your problem-solving abilities.

Even the best of friends get a little saucy from time to time. You’ll be fine finding friends for travel as long as everyone communicates.

Love this kind of thing? Check out more travel tips:

• All of the Best Travel With Friends Quotes
• Things You Learn from Nomadic Travel
• Unique Gifts to Gift Your Traveling Pals
• The Types of Hikers You’ll See on the Trails
• You Can Take Better Pictures of Yourself!

Destinations that are perfect for your next friend trip:

• A Detailed Itinerary for Nashville Travel
• Should You Travel to Sonoma or Napa?
• Our Favorite Day Trips From New Orleans
• Paris Should Always Make Your Trip List
• A Guide to Planning Trips to Saugatuck

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