11 Questions You Should Ask Before Deciding To Travel With Someone


Every time I hop in a car, grab a train or board a plane with a new travel buddy, I send a little plea to the universe: “Please let us travel well together.” I cross my fingers for smooth sailing through selecting restaurants, conflict-free days on the road and a matching sleep schedule. But that’s not always how things turn out.

Finding your ideal travel partner is a hybrid between interviewing for a job and creating a dating app profile. You have to talk about your strengths and weakness — and your ideal Friday night.

Although there are some issues you can only discover via passive aggressive anger walks through famous squares or fed-up stops for emotional ice cream eating, your exploration partner doesn’t have to be a total mystery before heading out on a trip. Here are 11 questions to start the vetting process before you planning an adventure with a new companion.

1. What are your reasons for going to this specific place?

Some people want to go to Paris to shop, and some want to spend all day in the Louvre. You may want to go to Denver for the breweries while your friend wants to do day trips into the mountains. All are fun, valuable travel styles — but they don’t mesh well.

It’s not like you have to agree on every single cool thing to see or do. (But I’m assuming you do like this person you want to travel with and think their interests are vaguely appealing.) You just have to make a conscious, intentional effort to fit everyone’s priorities into a trip itinerary, and you have to be okay with tagging along to some things you might not find utterly thrilling.

2. How together do you want to be?

Even when traveling with my best friends in the entire world, I save some time for solo exploring. However, some people envision a trip where you stick together forever and do every activity jointly. That dynamic can make one half of a travel duo feel stifled while the other might feel abandoned. So talk honestly about expectations and explain your comfort levels.

Another social dynamic that’s worth a chat: Travel friends you might meet along the way. Are new companions welcome to join in your fun or is this a special bonding trip for you and your pals? This is a detail that is hard to compromise on. If someone wants quality time, you might have to give up the idea of meeting new besties on the road.

3. Are you flexible in your travel plans?

Now, I’m not talking crazy flexible. We all have monetary limits and most of us don’t have unlimited vacation days. But Type A folks who get pretty set on an agenda may not want to travel with the whimsical oh-that-looks-interesting types. Or maybe you specifically do want to just wander around and play things by ear. Either way, you’ll want to discuss how much lead time you want for travel decisions— big and small.

4. What’s your trip budget?

Yes, talking about money can be uncomfortable, but it’s crucial for travelers. Besides the obvious flight costs, you need to discuss whether you’ll be lunching on grocery store sandwiches or brunching in the hottest restaurants in town.

Contrary to popular belief, you can travel with a friend who makes significantly more (or less) money than you do. But the wealthier traveler has to be willing to pinch pennies on the non-negotiables, such as flights and lodging. And the one strapped for cash must either accept help paying for certain activities (if offered) or bow out gracefully. It’s not easy and it takes an incredible amount of self-awareness, but it is possible.

5. How much sleep do you need?

Early birds and night owls can successfully travel together if you talk it out. You can totally compromise on a couple late nights or crack-of-dawn mornings, but overall, you want to travel with someone who follows the same sleep cycle as you. No one is a happy camper after missing out on hours of sleep they’re typically used to.

6. What does A night out look like?

A post shared by Kate McCulley (@adventurouskate) on

Before bedtime, you gotta talk about your evening plans. Are y’all partying? Are you asleep by 10 p.m.? While I think the most rewarding travel experiences alternate nights out dancing with long nights at sidewalk cafes with a bottle of wine, some destinations offer more of one type of night than the other.

We all have nights where that margarita is more tequila than lime and things get a little tipsier than planned, but make sure your travel buddy wants to come along for that ride before ordering marg number three. (And the same goes for all other substances — no matter if you’re in Amsterdam or Bali.)

7. Do you need special food?

A post shared by Markella A. (@doyouspeakgossip) on

Gluten-free, vegetarian, Paleo, lactose intolerant, vegan or keto — if you have any dietary restrictions, your travel companion needs to know. And if you’re super picky, let’s talk about that, too. It all changes how much food research needs to happen before grabbing dinner, so spontaneous travelers will need a warning to mitigate expectations of just choosing charming corner bistros on a whim.

Foodies, this chat applies to you as well. If you are insistent on eating the absolute best arepas in Colombia or determined to hit every Insta-famous spot in Seoul, clue in your future partner in crime that they might need to wait in some lines for their grub.

8. How far is too far to walk?

It doesn’t really matter whether you’re heading to the mountains or a giant city. You have to talk about walking. A two-hour hike might satisfy one traveler, while another explorer might want days on the trail. And if someone doesn’t pack fab walking shoes, there’s no way you’re walking for hours on end through a city.

9. What’s your transportation of choice?

Speaking of transportation, how are you getting around? You’ve got a lot of options: solely walking, biking, public transportation, ride-sharing apps, taxis and renting a car. But each of these involves a difference in cost and time in transit. The urban biker might not travel well with the frequent cab hailer, so just be mindful of these differences.

10. How much does travel stress you out?

Are you holding the armrest with a white-knuckled death grip when you get on a plane? That’s okay — a fear of flying is super common. But if you’ll need serious emotional support, just give your future travel bestie a heads up so they know not to worry about you if you freak out a little bit.

Also, if you’re an old pro at traveling, be patient with the anxiety-ridden. You had your first big adventure once, too.

11. How much do you care about getting the perfect photo?

A post shared by L e i r e (@leyre_) on

Alrighty, Instagram queens, this one’s for you. You must discuss photography. Traveling with a fellow ‘grammer or aspiring photographer will be fabulous. You can swap tips and arrange the perfect shots for each other. But if you’re exploring the world with someone who only takes a single snapshot of the big sites, you might need to set a time limit on how many pics you can take of your wine glasses before you drink the darn things.