Traveling With a Friend? Ask These 7 Questions First (Or, How To Travel Together Without Destroying Your Friendship)

Traveling With a Friend? Ask These 7 Questions First (Or, How To Travel Together Without Destroying Your Friendship)

Nancy Mitchell
Jul 26, 2016
(Image credit: oneinchpunch/Shutterstock)

Last week, inspired by the New York Times article about questions you should ask your partner before you get married, we compiled a list of 11 questions you should ask your roommate before moving in. And this week, we're tackling another pairing, one that can be almost as rewarding as marriage or cohabitation, and potentially just as fraught: traveling with a friend. If you've ever had a blowout fight with a friend on the streets of Barcelona, you'll understand the importance of asking these questions, and if you haven't, well — you should definitely read this list.

Are you a planner? Or do you prefer to be more spontaneous?
In my opinion, this is the most important thing to get straight (and hopefully be somewhat compatible on) when planning a vacation with someone. Some people are planners and really, really like to know in advance what they'll be doing pretty much every moment of their vacation. Other people prefer to be completely spontaneous. A lot of people fall somewhere in the middle and like to have a general idea of the schedule for each day, but with room to work things in at the last minute. Before you set out, find out which one your travel buddy is, and whether you two are willing to accommodate each others' styles.

What is your preferred schedule?
About what time do you like to wake up every morning? When do you prefer to go to bed? Are these times flexible if you, say, have a big night out on the town? Do you like to nap in the afternoon? (You may laugh, but in my opinion a good nap adds a great deal to the enjoyment of a vacation.)

What's your idea of a good time?
When you're in a new place, do you like to go to museums? Hike? Shop? Try out all kinds of restaurants? Check out the local nightlife? Just wander around? It's possible for two people to have very different ideas of what constitutes a good vacation, so make sure you and your buddy are on the same page.

What's the ideal size for a group?
If you're planning a vacation that involves more than just the two of you, have a chat with your prospective travel partner about the ideal size of the group.

What's your communication style?
If you're good friends with someone chances are you already know whether they're very direct or tend to be more subtle with their communication — but this is a good thing to keep in mind while planning your trip, and during the vacation itself.

How adventurous are you/open to danger?
For some people, taking public transportation late at night in a strange city is an adventure. For others, it's a risky and terrifying brush with death. If your companion's danger threshold is much higher or lower than yours, this may lead to a little friction, so discuss it now.

How much money are you willing to spend?
We get it: talking about money is awkward. But it's even more awkward in the context of a heated discussion about where you're going to dinner that night. If you're the kind who likes to be spontaneous and pick destinations at the spur of the moment, definitely have a chat with your travel partner beforehand about your budget for the trip, and what you're willing to spend on meals and activities.

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