Despite all my blog posts about how great solo travel is, I know some of you might not be ready to travel alone yet. You want to get your feet wet just traveling at all, but you don’t have an obvious person to travel with. So you desperately start looking around for someone—anyone–you know who might be willing and able to go with you. Like your coworker, your cousin, your childhood best friend. Stop right there.
How many vacations do you get every year? Do you really want to ruin it by choosing the wrong travel companion? Just because we get along well with someone in our everyday lives doesn’t mean we’ll travel well together. Your best friend could wind up being your worst nightmare by the end of your trip. Annoying habits that you normally overlook become magnified tenfold with too much togetherness.
How can you find a good travel companion, then? The same way you find a good employee, or a good dogsitter, or a good anything. You interview them. Or rather, you interview each other. A few years ago, my friend Colleen expressed interest in coming with me on one of my trips to Vegas. I was excited about this, because I thought it would be fun to have someone to show “my” favorite city to. And we always got along great. But I’m also an introvert who had lived alone for many years and wasn’t used to being around someone else 24 hours a day. I foresaw the potential for disaster if we weren’t on the same page.
So before we agreed to take the trip together, we met for coffee and questioned each other about our travel styles, budgets and needs to see if they lined up. We also negotiated certain aspects of the trip ahead of time. By the time we took the trip, we both knew what to expect from each other and were very satisfied with the vacation.
Below are some questions you might want to ask each other. “I don’t care” and “whatever you want” are not acceptable answers. Be honest about your preferences. When it comes to dealbreaker items, jointly set the ground rules ahead of time. If during the trip your companion violates one of them, don’t hesitate to remind her of your agreement. Or if some issue arises that you didn’t anticipate, talk it out immediately.
Travel Compatibility Questions
- Are your budgets and tastes compatible? If one of you wants to stay in a hostel while the other wants to a 4 star hotel, you’ve got a problem.
- If you are flying to your destination, what is more important to you: Cost of flights or convenience of flights? Are you willing to take different flights from each other and meet there?
- Are you comfortable and/or willing to drive in a strange place?
- Are you a planner or do you prefer “winging it”?
- Are you a night owl or an early bird? Do you snore, suffer from night terrors, or walk in your sleep? Any other weird nocturnal habits you’d rather no one else know about? (Then you might not want to share a room.)
- What do you hope to get out of this vacation? I recommend each person jot down all of the things they want to do on the trip, circling the top 3-5. Compare your lists and make sure each person gets to do their top 3-5, even if it means splitting up for part or all of a day. If you have NO items in common on your “list of things to see and do,” chances are, you really aren’t compatible travel companions.
- Are you an introvert or an extravert? A positive person or a negative person? These kinds of opposites can drive each other crazy sometimes.
- How independent are you? Are you comfortable splitting up for an afternoon or a day and just meeting up for meals? Talk it out up front. If it would drive one of you batty to have someone stuck to you like glue for the whole trip, you need to find out before you go.
- Do you have compatible life habits? Do you smoke? Is one of you a vegetarian? Are you a heavy drinker or drug user? Do you have allergies or aversions to strong scents? Phobias?
- Are you looking to “hook up” or “get lucky” with someone on this trip? If one or both of you are, and you’re sharing a room, you’ll need to negotiate use of that space.
Two more tips:
- Negotiate ahead of time how shared expenses (like miscellaneous hotel charges) will be handled.
- Once you have found a suitable travel companion, be sure to exchange emergency contact information as well as information about any potentially life-threatening medical conditions, just in case.
One final piece of advice: I recommend building in some solo time to your trip even when you do have a travel companion. If the two of you get a breather from each other once in a while, you’ll appreciate the time you’re together that much more. You’ll see how much fun you can have doing things on your own in a new place. And it might give you the confidence to go solo next time. Baby steps, after all.



on May 10th, 2011 at 6:16 am
[...] Finding the right travel companion [...]
on May 11th, 2011 at 11:25 pm
Good tips, especially the money concerns. That’s always the biggest problem when traveling with someone else.
I always like the take separate flights, even with the best of friends. (Then again my best friend hates flying and gets ridiculously drunk before each flight, so maybe I’m biased).
on May 24th, 2011 at 11:15 am
I like the one about choosing 3-5 goals you plan to get out of the trip and then if they don’t match, take a day break from each other to explore your own personal stuff. Even if you did have many matches, there’d be one thing you need your own time and space to do.
on May 24th, 2011 at 4:41 pm
@Jenna – Well, that’s as good a reason as any to take separate flights!
@Christine – Yeah, me too. I’m a big advocate of spending some time apart from your traveling companion during a trip, no matter how much you like them. It’s just good for you.