Travel Tuesday: How to Travel with Your Best Friend and Not End Up Ex Friends

by Christina Pesoli on October 20, 2015 in Travels,
BFF travel

Going on a trip with your best friend? Great idea—in theory, at least. But if the trip ends up costing you a perfectly good friendship, you’d be better off staying at home.

The answer isn’t to limit yourself to traveling only with people you wouldn’t mind never seeing again. The key is to implement measures and mindsets to maximize the fun and minimize the friction. The following itinerary will set you up for smooth sailing.

Think it through. Who you travel with is just as important as how you get there and where you go. You can be very close friends and incompatible travel companions all at the same time. If splurging on hotels, meals, and shopping is part of the joy of vacationing for you, Frugal Frances is probably not your best vacation buddy, no matter how great you ordinarily get along in your every day life.

It’s up to you to recognize travel incompatibility even when your friends don’t. I once convinced a close friend who was an experienced camper to let me join her on her annual beach campout—even though I had never camped before and didn’t like to be outdoors for longer than it took me to get from one fully air conditioned chamber to the next. The trip didn’t go well, but we both learned something. And neither one of us has made that mistake again.


Embrace technology. There are plenty of apps that can help you avoid bumps in the road while you travel. For example, unless getting lost is part of the experience you’re going for, use a navigation system when you’re road tripping in areas you’re not familiar with. It will save you time and aggravation, and that will keep you from taking a wrong turn to Crankytown.

Eliminate another possible source of tension by using apps that help you to keep track of who owes how much money and to whom. Splitwise is one possibility. Simply input who pays for what as you go along and the app pretty much does the rest. It will even generate friendly IOU emails at the end of the trip so that one friend doesn’t have to nag the other for payment.

Divide up tasks—both the fun and not-so-fun ones. When it comes to things you both want to do, take turns. If you both like to drive, divide the trip into two hour shifts. If you both like to be in charge of the music, let the one who’s riding shotgun be the D.J. If you both like choosing restaurants, divide up the nights that you’ll be eating out, and each of you can research restaurants and make reservations for your designated nights.

When it comes to tasks neither one of you likes to do, the advice is the same. Split up the responsibility for the no-fun tasks so that they don’t fall to just one person or not get done at all—because either of those scenarios can lead to friction.

When it comes to stuff that only one of you enjoys, the person to whom that task should fall is obvious. If one of you really doesn’t care where you eat dinner, but the other one considers himself a bit of a foodie, recognize that meal planning is something the foodie can bring to the table, so to speak.

Overall, try to keep things even, work-wise. It’s okay to divide and conquer, but only if you’re actually dividing. Without the dividing part, you risk getting into a situation where someone is being either lazy or controlling, and neither one of those feels good to be around for long.

Be flexible. “If you want to make the travel gods laugh, tell them about your plans.” That’s how the saying goes, more or less. But the fact that things won’t always go according to plan doesn’t mean you shouldn’t make one; it means you need to know how to roll with it when it doesn’t.


If your flight is delayed and that in turn means you won’t make it to your destination in time for your 7:00 p.m. dinner reservation at that restaurant you’ve always wanted to try, don’t start badgering your bestie about how you guys should cancel the reservation she made the next night at her favorite restaurant because you didn’t get your turn. There’s a difference between trying to set things up in a way to keep everything more or less equal, and being an ever-vigilant scorekeeper of travel rights and wrongs. No one likes to travel with a scorekeeper.

If you’re taking a trip to NYC to take in some amazing Broadway shows and the airline loses your luggage, don’t recast your trip as a tragedy about a woman victimized by an evil airline starring you. View surprises (both good and not so good) as part of the adventure. And take comfort in this truth: Years later when you reminisce about your trip, your favorite stories are likely to involve the times when things didn’t go according to plan, rather than the other way around.

Give each other some breathing room. No matter how much you and your travel companion enjoy each other’s company, give each other some space once in awhile. If your friend wants to faction off on her own for a couple of hours, don’t freak out. You’re not conjoined twins; you’re not a guard transporting a prisoner from one jail to the next; you’re two friends on a vacation. There’s going to be plenty of togetherness (much of it in very close proximity), so you don’t have to worry about that. What you do have to worry about is the quality of that time together. And a little time apart can go a long way toward keeping people from getting on each other’s nerves. So, head to the hotel gym while your friend watches The Bachelorette back in the room. Both of your moods will be better as a result, I promise.

By Christina Pesoli

Christina Pesoli practices family law in Austin, Texas. She writes regularly for Huffington Post on relationships, parenting and divorce. She is also the author of Break Free From the Divortex: Power Through Your Divorce and Launch Your New Life. You can find more of her articles on her website: