9 Tips to Travel with Friends and Keep Your Friendships

—Amy M. Gardner

“This is the true story…of seven strangers…picked to live in a house… and have their lives taped…to find out what happens…when people stop being polite…and start getting real.”

The Real World.

I think about that line every time I travel with friends.  There’s nothing like being out of your comfort zone and in an unfamiliar environment, whether for a weekend or a week, to help you get to know the “real” person.  

I’ve been traveling with friends since my German class trip my junior year in high school.  Since then, I’ve been part of a group of 20 where I only knew one person in advance (a 3.5 week trip to Europe as a German Marshall Fellow), many trips where Keith and I have traveled with one or more other couples, some trips where Keith and I have traveled with one single friend, and several trips where I traveled with just one or two friends.  I’ve also organized many group trips for family members.  Here are nine tips to help you avoid the mistakes I’ve made.  

Waiting for the train with friends, in Italy, 2015.

Waiting for the train with friends, in Italy, 2015.

1. Take a practice trip.

If possible, take a shorter trip together before you set off on a longer trip.  On a shorter trip, you can see some yellow flags and know what you’re getting into before you find yourself on a bigger trip farther from home. 

2. Set clear expectations.  

One friend intends to take a big city by storm, running to every museum, monument, and historical site with the zeal of a person who will never travel again.  The other wants to take it easy, taking long naps and leisurely dinners.  They can still travel together, but figuring out that difference in expectations before you take off will make the trip itself much more pleasant.  

A few suggestions: 

  • each person can alternate planning a day, meaning half your trip will be jam-packed and half will be more leisurely; 

  • the person wanting more of a vacation can get to the destination first to have time to decompress, or stay later to relax afterwards; or

  • the person wanting to do more could go on their own in the afternoons (or join walking tours if they aren’t comfortable on their own) while the other person rests.   

As another example, maybe one person wants to spend every waking moment together, while others want to do things on their own, or one person only wants to eat every meal at American chain restaurants and the others want to experience the local cuisine (true story).  Again, much better to find this out and figure out a solution in advance.  

3. Communicate in advance.  

Whether through Facetime or a shared Google doc, communication before your trip is critical, both in terms of setting clear expectations, but also in avoiding frustration during the trip.  Even if the communication is just to establish that you aren’t going to plan anything in advance, again, it’s better to know that up front.  

4. Discuss the budget and adjust as necessary. 

This can be tricky, but I’ve seen each of the following scenarios:  One friend wants to have lobster and split the check every night, while the others don’t want to subsidize that.  One friend believes that as the person with the smallest salary, the other friends should subsidize her part of the trip.  One friend doesn’t want to say that he can’t afford the trip the other friends are planning, goes on the trip, resents the cost, and ends up resenting the friends.  

Instead, talk about the budget up front, and figure out how money will be managed.  Here are a few ideas that have worked on trips I’ve been part of:

  • take turns planning and paying for meals, with everyone paying their own admissions and other costs;

  • have one person be the “bank” and cover all costs for the trip, with everyone else paying her their portion at the end; 

  • agree on targets for your largest expenses in advance; or

  • alternate with one person paying for everything one day, another paying for everything the next.  (On longer trips, this theoretically averages out.)      

 5. Talk about issues that come up during the trip.  

No two (or more) humans can possibly be 100% happy with each other every single moment of every day.  When irritations come up, be honest about them so they don’t fester.  When a friend was late a few times on a trip and realized I was annoyed that I had been hustling to be ready on time when she was arriving calm, cool and collected (and late), we talked about it and agreed to adopt a grace period.  We aim to be ready by a certain time each day, but there’s a 5 minute grace period.  I’m no longer stressed about being ready on time, and she doesn’t have to worry that if she is late, I’m going to be annoyed.  

On the flip side, don’t let yourself vent to other people on the trip.  It just creates bad feelings.  Even when Keith and I are traveling together with other people, we never talk about them because we know that no good comes of it. 

6. Create rituals. 

Whether it’s a glass of wine before dinner, an early morning run together, or sharing joys and challenges at dinner, create rituals that help you connect and build your bonds.  

7. Anticipate and prevent tension points.

Maybe one friend is very anxious on airplanes.  Maybe another hates transitions, and another gets cranky without an afternoon snack.  Whatever it is, acknowledge and try to prevent tension points when you can, and be ready to address them before they get out of hand when they can’t be prevented.

Booking separate rooms on longer trips so everyone can have their own space, for example, can be helpful for people who need time to decompress.  

Knowing that the wives were not interested in driving a manual transmission car, and that navigating windy rural roads in a foreign country was not going to be easy, on one couples trip we and the other couple decided to have one husband drive while the other wife navigated.  That way when the navigation was inevitably off or the driving included rolling into a wall, the conversation was much more polite and kind than it might have been if it was a married couple in the front seats.

8. Don’t try to do too much.  

If you’re traveling alone, you might be able to see everything you want.  But when you travel with someone else with different likes and dislikes, it becomes impossible to see everything everyone wants to see.  Instead, have each person suggest no more than 3 ranked must-sees, and plan your trip around those.  You’ll avoid running yourself ragged, leave time to relax together, and going off of everyone’s preferences (rather than one trip planner’s picks) means you’ll have a richer experience.  

9. Remember part of the appeal is being with friend(s).  

If you wanted everything to be done your way, you could go on your own.  Having decided to do a trip with friends, you’ve opened yourself up to an experience that’s different than you could or would have had otherwise.  

My friend Katherine, a former archeologist, has taught me about the history of a city wall with a passion I could never have imagined, our friends Kristy and Matt helped us to appreciate the value of engaging and befriending other travelers (and to take a cooking class in Italy that became one of my favorite travel memories), my friend Martha taught me that some of the best travel meals can be made up of food you point at with zero idea what it is, and my German Marshall Fellowship friends taught me the value of guidebook with good restaurant recommendations, just in case.  None of these would have happened if I hadn’t traveled with friends, and remembering that makes it much easier to appreciate the opportunity when someone hogs the bathroom or insists on reading every plaque in a huge art museum.

If you’re lucky enough to have friends with whom you want and can travel, count yourself lucky and take advantage of it.  And hopefully if you follow these nine tips, you’ll find yourself planning the next trip before the first one is over.