How To Travel With Your Friends (And Remain Friends Afterwards)

A summer jaunt with your friends can be a source of beautiful memories — or an expensive deathmarch of awkwardness and acrimony. Here’s how to make sure it’s the former.

Choose your friends wisely.

Or at least your travel friends. Lucy Jane Bledsoe, author of The Big Bang Symphony and The Ice Cave: A Woman’s Adventures from the Mojave to the Antarctic, told me,

I probably wouldn’t travel with someone who had radically different ideas about what she wanted to do and see. Travel is one of my biggest joys in life, so I like to do it with people who share my ideas of fun and interest.

Stephanie Elizondo Griest, author of 100 Places Every Woman Should Go, added, “If the friend that you’re considering traveling with won’t even look at sushi, do you really want to be traveling with them?” Obviously you and your friends don’t have to be perfectly in sync all the time, nor do you have to do all the same things (more on that later). But you do want to pick traveling companions who share your basic outlook. If you love lounging in hotel rooms, you may not want to plan a weeklong trip with your pal the backpacking skydiver.

Pool your money.

I talked to Marybeth Bond, founder of Gutsy Traveler and author of Best Girlfriends Getaways Worldwide, who says, “When you start to plan, put $100 into a nonrefundable kitty. And that way, if anybody backs out, they lose the $100, but it isn’t such a big hit to everyone else.” Obviously the amount of money can vary, and it may not be appropriate in certain situations, but pooling deposits can be a good way of forestalling the last-minute cancellations that can throw a wrench in plans. Then, depending on the nature of the trip, everyone can add to the kitty later on for further shared expenses. Bond also mentioned another novel strategy: a group of women she once interviewed picked a different destination every year and pooled the money for airfare to reach it. That way each one paid the same amount for her ticket, even though they were coming from different cities.

However you choose to divide things up, it’s smart to create a pool at the beginning so that everybody pays equally for shared expenses and everybody’s invested — literally — in the trip. Then if one person wants to do something more pricey — splurge for a single room in a hotel, say, or take a solo day trip — she can pay for it herself. Bond adds, “the most important thing about splitting money is that you’re all on the same page about what your budget is and how you like to travel.” Have a conversation beforehand about what everyone’s willing to spend so that no one feels pressured or deprived.

A word on income inequalities: Griest says friends with drastically different incomes can split travel expenses proportionally, but this might make things uncomfortable unless the friends are very close. Also, it’s probably less awkward if the one with more money proposes the proportional split. Bledsoe also suggests that the friend with more cash can “try to find ways to pick up the occasional extra bill without making a big deal out of it.” And if you need tips for talking to friends about money issues, we’ve got that covered too.

Discuss your itinerary beforehand.

Even among groups of like-minded people, there are going to be some differences in travel preference. Says Bledsoe, “Talking about comfort levels before the trip is always a good idea.” Maybe one person really wants to go white-water rafting while the other prefers a light day hike — if they talk it through beforehand, “hopefully, it can be worked out so that the adventurous partner can go do what she wants to do without the other one feeling abandoned.” Bond advises that if you’re in a group with different activity levels, “try to make the really active things half a day, so those who are less active aren’t completely cut out.” And if you’re planning a really hard-core adventure trip, be clear about that from the beginning — you don’t want your friends expecting to read Proust when you’re packing for Half Dome.

Bond points out that one good way to get an itinerary together is to appoint a head planner. She says, “One person has to take the initiative and start it.” That person “becomes the spearhead and sends around an email to everyone saying, ‘here are four choices, which do you like?'” The email should also make clear that if someone doesn’t respond, you’ll vote without her. Putting one person in charge of getting plans started can be a great way of cutting through inertia and motivating people to make decisions — but as much as possible, everyone should be involved in those decisions. Your head planner is just in charge of getting the ball rolling — not dictating the entire trip.

But leave room for spontaneity …

Says Griest,

What’s really magical about traveling is that ideas tend to occur to people simultaneously, which is really interesting. You’re out with someone you just met at a cafe and then you look over at the person next to you and they say, “I just got back from the most amazing thing,” and they tell you about it and you both immediately want to go, and you go together. I’ve ended up traveling for months with people this way. […] I think that these organic processes are really what make traveling delightful.

Bledsoe adds that she thinks of travel “the same way I think of my book group — I wouldn’t go those places (or read those books) on my own, but this is an opportunity to expand my natural tendencies. Travel is all about expansion, right?” Some planning is definitely a must, but don’t schedule every minute. You want to allow time for you and your friends to discover new things, together and separately, and for you to learn from each other and from the other people you might meet along the way.

… and downtime.

When I asked Bledsoe what was the best way to relieve tension when you’re traveling in close quarters with a friend, she said, “Time alone!” As much as traveling with friends can be a great opportunity for camaraderie, it’s also important to build in some opportunities for solitude. Bond recommends emphasizing in advance that not everyone has to do every activity, nor does everyone need to be joined at the hip at all times. She offers this suggestion:

Discuss beforehand that you’ll be taking time out for yourself, and give your roommate — and ask her if you too could have — maybe an hour alone in the room. Go out for a walk, go down to the lobby, do that window-shopping in the neighborhood you want to. Each person should be able to have a little bit of time alone in the room.

Whether it’s time in the hotel room or a solitary hike, giving each friend time to him- or herself is great advice. You want to bond with your friends on your trip, but you also want to avoid killing each other, and taking a little breather every now and then is a great way to ensure you don’t drive one another insane. Griest adds that if any conflicts come up, “it’s pretty important to address things really early on. […] You’re actually going to need to do it probably even quicker than you would in a normal situation, because things quickly grow so intense when you’re traveling or on the road. I would say you want to be as open as you possibly can about things that bother you.” If you give your traveling companions plenty of space and address issues before they become problems, you should be able to have a fun and stress-free trip — and pave the way for many more to come.

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Lucy Jane Bledsoe [Official Site]
Stephanie Elizondo Griest [Official Site]
The Ice Cave: A Woman’s Adventures From The Mojave To The Antarctic
100 Places Every Woman Should Go
Gutsy Traveler [Official Site]
Best Girlfriends Getaways Worldwide