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Home » Should we travel together? Ask these questions before planning your trip
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Should we travel together? Ask these questions before planning your trip

Editor-In-ChiefBy Editor-In-ChiefOctober 25, 2026No Comments6 Mins Read
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A bombing at the Colosseum, a laceration atop Mount Kilimanjaro, a window seat crash. Having travel companions you don’t get along with can ruin your vacation.

As experts in friendship, travel, and decision-making, we know that the stress and complexity of travel, not to mention the nearly endless number of decisions that must be made, can put tremendous pressure on a relationship that was perfectly enjoyable within a 10-mile radius of home. There’s a reason people say to travel with someone before you get married.

A Booking.com survey conducted in July of 1,253 U.S. adults who had a sleepover in the past 12 months found that 35% of travelers felt like they didn’t fit in with their travel companions. 21 percent of respondents have even quit a trip because of a travel partner, and 28 percent have considered ending a relationship or friendship with an unsuitable travel companion because of a bad vacation.

The problem is that we may have different unspoken expectations about what the holidays entail. One person wants to book activities from sunrise to dusk every day, while the other wants to lounge in the hotel spa until cocktail hour? Who wants to go all out with seafood towers and champagne while the rest of the group prefers to nibble on convenience store hot dogs and guzzle local beer?

Not all friends, lovers, and family members are suitable travel partners for you. Understanding that before planning your itinerary will save you time, money, and disappointment.

Ask questions about travel compatibility before booking

We’ve created a quiz to help you quickly determine your compatibility with a potential travel partner so you can avoid potential headaches down the line.

Here are six of the most important questions.

1. What kind of accommodation do you envision? Are you comfortable sharing?

Let’s start with the basics. Some of us pass out in the middle of a nightclub. Some people need white noise machines, blackout curtains, and a room to themselves. The hotel, hostel, or apartment you visit during your trip is key to your compatibility on the road. It’s difficult to have a blissful holiday when you’re exhausted by other people’s snoring.

2. Would you like to check your luggage?

The debate between carry-on and checked baggage will never go away, and this is one difference it’s wise to consider in advance. Who doesn’t want to spend days carefully choosing the most stain-resistant t-shirts, simply stuffing them into their backpack, only to see their partner arrive at the check-in desk with two of their largest suitcases? This doesn’t have to be a holiday arrangement, but discuss it so everyone understands what will happen.

3. What would your dream vacation look like?

Is your dream vacation full of lazy days wandering around, entering interesting shops and cafes, and taking afternoon naps, or is it filled with museums, restaurants, activities, and exercise?

For some people, “vacation” means downtime, with few scheduled activities and lots of white space to do whatever feels appealing at that moment. For some, there’s no point in leaving the house unless you’re making the most of your time, and leaving a destination without visiting every dot on a detailed Google map is a wasted holiday.

4. How long does it take you to get ready in the morning?

This may seem trivial, but more than one trip is taxed by a long morning routine. Some have their hair styled and eyelashes glued on. The other, wearing the same clothes as yesterday, is tapping his foot, waiting for departure.

If you’re not compatible in this respect but still want to travel together, it’s a good idea to decide on a strategy in advance. Maybe it’s okay to go exploring alone, have coffee, or eat your hotel breakfast alone. Alternatively, travelers who need more time to get ready can commit to setting their alarms 45 minutes earlier than their fellow travelers.

5. How much do you plan to use?

Want to travel cheap? Or can’t get out of bed with less than five stars? In a Booking.com survey, 35% of respondents said they’ve gotten into an argument with a fellow traveler over money.

Budget considerations may be the most important thing to discuss before committing to anything. Ideally, each person would set a travel budget, set an amount they are perfectly comfortable spending, and compare to see how far they are from themselves.

If one of you is dreaming of an airport limousine ride and the other is planning on grabbing rolls from your hotel breakfast for lunch, you might be better off taking separate trips.

6. Do you get offended if your travel companion listens to music on headphones or opens a book?

Have you ever been stuck in a plane seat next to someone who won’t shut up? Compatible travel means more than just similar tastes in food and accommodations. You’ll be spending a lot of time with your travel companions.

Why not have a quick chat before boarding the airport shuttle? Are you okay with both of you doing your own thing during the boring parts of the journey, or do you expect to hurt the other person’s feelings if one of you prefers to be “on” 24 hours a day and the other devoted to the podcast?

Compare answers and make a call

Once each potential traveler has answered their questions, review them together and discuss and decide whether to travel together.

If you disagree too much, shake hands and agree to keep the hangout local. If you’re pretty much on the same page, see if you can plan a trip that works for both of you. For example, if your ideal activities and costs don’t align, you might split up one day and just get together for dinner, or you might set up a restaurant budget together in advance instead of coming up with a restaurant budget on the fly and then running home with a big credit card bill. If you give the same answer to all the questions, congratulations. Now, book your tickets!

Anna Goldfarb is a friendship expert and author of Modern Friendship: How to Nurture Our Most Valued Connections, a must-read for the Next Big Idea Club. She is the author of “Substack Friendship Explained.” She has been featured in The New York Times, The Atlantic, The Washington Post, WIRED, The Oprah Daily, Goop, and more. Follow her on Instagram.

Nell Wolfhart has been helping people make big (and small!) decisions since 2013. Her clients include politicians, hedge fund managers, Netflix executives, poets, parents, medical students, and more. You can listen to her coaching sessions on her podcast, “The Decision Coach.” Find her at Decisioncoach.com.

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