It’s one-o’clock in the morning and I’m trudging up a steep cobblestone hill from our late-night meal. I’m cursing my falling-apart flip-flops, our early morning red-eye, and the fact that no one wanted to take a cab back to our Airbnb. I’m starting to regret saying yes to this friends’ trip.
I love my friends. But I struggle to stay up past 10 p.m., and I’d much rather take a cab when it’s dark and there’s a steep hill involved. If I had known up front about our different travel budgets and styles, I could have avoided feeling frustrated and angry. Here are four questions I usually ask — learned from experiences like this one — to determine whether or not someone will be a great travel partner for me:
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What are your travel priorities?
Before a recent business trip, I asked my colleague what would make him happiest about being in Nashville. That kicked off a longer conversation about why we travel and what activities suit us best, so when we did have time to explore, we made the most of it. The good news? We both had the same top priority, which was eating as much amazing barbecue as possible.
When I’m in a new city, I love to try the famous food in that area. Whether it’s pizza in New York or paella in Valencia, understanding a new culture through the lens of what’s on the menu makes me happier than anything.
How early do you get to the airport?
There are two types of people at the airport: early birds and last-minute door-closers. After once having to hustle through the Vancouver airport when my flight changed at the last minute, I fall squarely into the “so early the flight isn’t even listed” camp. I think the stress would kill me if I was traveling with a “run through the airport or bust” type of person. To solve this dilemma, I meet my travel buddies at the gate.
Beyond your initial voyage, this question provides insight into a person’s general style. How likely are you to miss a dinner reservation, guided tour, or ticketed show during your trip and how do you deal with that stress? There’s no wrong way to go about it— just make sure you know ahead of time. Having an honest conversation about how you both approach planning and punctuality can help you determine if you’ll gel well together.
How much do you like to plan?
If you couldn’t tell already, I’m a super planner. I’ve got timelines, manila folders stuffed with lists and maps, and jam-packed itineraries. I tend to make everything from dinner reservations to tour bookings well in advance.
That style can feel suffocating to someone who wants to discover a destination with more of a free spirit. I always ask anyone I’m traveling with how much of the trip they like planned in advance. If they would prefer less structure, I build wandering time into my itinerary — and take it easy on the reservations — so it suits both of us.
What’s your budget?
Be super honest with your traveling companions about how much you’re willing to spend or else you will be miserable. It can get awkward fast if you’re psyched about a museum and your partner asks to wait outside. Or if you sit down at a restaurant you’ve been dying to try only to have your partner ask to leave. Avoid those moments by talking honestly about what you want to spend money on — do you want to splurge on that Eiffel-Tower view or save your pennies for a walking food tour? — and be willing to compromise.
As for that steep cobblestone hill, I called a “family meeting” with my friends over breakfast the next morning. Turns out, all of us would have rather taken a cab — we just thought the others felt differently. After laughing at ourselves, we went through the questions above, making sure we would all have a great time for the remainder of the trip. Turns out my friends are pretty great travel partners after all.
Originally published July 1, 2019.