Back to News

Before You Book That Trip Together, Ask These Six Questions

CNBCSunday, October 25, 2026

Blow-up fights at the Colosseum, tears on Mount Kilimanjaro, squabbles over the window seat - the wrong travel companion can sink a vacation.

The stress of travel and the endless decisions that come with it can strain even a friendship that works perfectly well back home. There's a reason people advise traveling with someone before marrying them.

In a Booking.com survey of 1,253 U.S. adults who had taken an overnight trip in the past year, 35% discovered they weren't compatible with their travel buddy. Twenty-one percent cut a trip short because of their companion, and 28% considered ending the relationship or friendship after a bad vacation.

The trouble often comes down to unspoken expectations: one person wants every day packed dawn to dusk, the other wants to lounge until cocktail hour; one wants seafood towers and Champagne, the other prefers convenience-store snacks and local beer.

Not every friend, partner or relative is the right person to travel with - and figuring that out before planning an itinerary saves time, money and disappointment. Six questions worth asking: What kind of accommodations do you picture, and are you comfortable sharing? Do you check luggage or carry on? What does your dream vacation look like - downtime or a packed schedule? How long does your morning routine take? How much do you expect to spend? And will you be offended if your companion tunes out with headphones or a book?

Compare answers together. Too many differences? Keep the hangouts local. Mostly aligned? Plan a trip that works for both of you - perhaps splitting up for a day and reuniting at dinner, or agreeing on a restaurant budget in advance. Matching on every question? Book those tickets.

Share this article

Find activity partners on your next vacation

Connect with fellow travelers at resorts, hotels, and cruise ships.

Get Started Free