5 Tips for Road Tripping with Your Best Friend

On September 18, 2011, I set off on a two-month journey across the United States with one of my best friends from college. Molly and I had met in the summer of 2007 and quickly discovered that we shared a bucket list desire to embark on the great American road trip.

After a few years of joking and dreaming about it, our stars, schedules, and finances aligned, and we hit the road in my red Nissan Versa. We had a GPS device but no smartphones, a rough route but no firm schedule, and a whole lot of Broadway cast recordings on our iPods. (Remember those?) What could go wrong?

Thankfully, not much did – at least nothing major, anyway. But even in the best of times, it can be challenging to spend twenty-four hours a day with the same person for fifty-seven days straight. I won’t say that Molly and I never annoyed each other, or that we never disagreed, or that things were always as perky and upbeat as the show tunes we were belting out. I will, however, say that we were able to fully enjoy each day of that trip, and that we came out of the experience even better friends than we’d been going into it.

Upon reflection, I recognized five choices we made that allowed us to maintain our sanity, civility, and friendship during the long hours on the road. Although we didn’t make them intentionally at the time, their effects had an impact on our enjoyment of the trip and our planning for future travel with other friends.

Here’s my best advice for surviving a road trip with your best friend!

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1.) Choose your traveling companion wisely.

My husband subscribes to the idea that, when it comes to relationships, there are three kinds of people: those with whom you can only stand to spend three seconds, those with whom you’re fine to spend three hours, and those with whom you can comfortably spend three days. The first step to enjoying your road trip is to make sure you’re not undertaking a three-week vacation with someone who, for you, is only a three-hour person.

Pick someone with whom you get along well, whose travel style and priorities match yours, and with whom conversation is generally easy and enjoyable. Make sure you can sit together in silence comfortably – there will be a lot of it on the road.

You don’t have to see eye to eye on everything, and along the way you’ll certainly learn things about each other’s personalities that you didn’t know before. That said, being intentional about choosing your travel buddy can save you a lot of headaches later when you’re facing unforeseen difficulties like a breakdown… or just enduring your seventh straight hour of driving together that day.

I have lots of friends and acquaintances whom I love dearly, but the number with whom I would travel for any length of time is not large. That’s okay.

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2.) Get on the same page before you leave.

In the months before our trip, Molly and I spent hours on the phone and Skype planning out the details. We mapped out potential routes, made lists of friends and family with whom we could stay, divvied up supply purchases, and researched things to do along the way. I was fortunate that Molly and I had similar goals for the trip and that we were both interested in taking part in shaping it together.

It’s perfectly fine if one person undertakes all of the research and planning, but it should be done with full consideration of the other person’s preferences, desires, and expectations. The more you discuss on the front end, the less potential for conflict you’ll have in the days and weeks to come. Understanding each other’s goals will also help ensure that both of you look back on the trip with satisfaction.

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3.) Involve others.

Most of our lodging across the United States was with friends, family, or CouchSurfing hosts, so it was rare that Molly and I found ourselves alone in a hotel room. We planned our route to take advantage of visiting far-flung loved ones, so a significant number of our sightseeing days were also spent with local friends and family. In addition, Molly’s sister, my then-boyfriend (now husband), and two of Molly’s best friends all flew out to join us for different multi-day legs of the trip.

Having other people along for the ride not only injected new life when we might have been tempted to slack off in our exploring but also provided a nice reprieve from having the same, single person for company for days on end.

If possible, visit family, friends, or friends of friends along the way. If there’s a person whom you think would fit easily into your crew (see the first suggestion, above), invite him or her to join you for a few days around the halfway mark or later in your trip. You’ll be amazed at how much of a difference it will make.

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4.) Take time for yourself.

Similarly to how adding a third person can relieve the pressure of being together 24/7, so can spending some time apart. Visit a local coffee shop to journal, or check your email at a table for one. Split up and grab lunch at different places if you can’t agree on one. Book a massage while she explores the city. Go for an early morning run before she wakes up. Don’t be afraid to take the time alone you need to refresh yourself.

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5.) Communicate, but don’t forget to listen.

This number one rule for any successful relationship may seem obvious, but it’s so important that it bears repeating here. Whether it’s an attraction that you want to see in a certain city or something your traveling companion has been doing for the past week that has been driving you crazy, talk it out calmly and respectfully. You don’t want to look back with regret on something you missed because you didn’t make your desires known, and you also don’t want to let little annoyances build and fester until you blow up in the middle of a three-hour drive across New Mexico. 

Similarly, listen with an open mind to what your co-pilot is telling you. Remember that working through some of those tougher conversations is imperative to both of you being able to enjoy the rest of your time together. Keep your pride (and your tongue) in check. It is also immensely helpful to go into any conversation assuming that the other person has positive intentions in whatever he or she is doing and that you just need to gain a better understanding. 

Molly and I are not naturally decisive people; the men in our lives still can’t believe we made it across the country when we can be so easily paralyzed by deciding what to order from a menu. It was, therefore, very important for us to speak up and communicate our desires in spite of our tendencies to just reply, “Whatever you want to do.”

Do you just want a night in to relax and watch Netflix on your phone? Are you really craving pasta for dinner? Does the way she packs the trunk make you nuts? Talk to her about it.

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Molly and I had an incredible time on our two-month trip across the United States. We shared a lot of laughs, took thousands of photos, and experienced some of the most breathtaking sights in this beautiful country. We enjoyed ourselves so much that we even reunited six years later for a quick weekend road trip through Iowa and Nebraska to knock those states off our lists, too.

Most importantly, we made invaluable memories together and solidified our friendship as one of the most important relationships in my life. I hope that these tips help you when you hit the open road, and that you have as unforgettable a time as we did!

See you on the road!

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What tips do you have for surviving long periods of travel with the same person?

What was the best road trip you’ve taken?

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Read More:

Midwestern Delights: A Long Weekend in Iowa and Nebraska
A Long Weekend in the Finger Lakes
Travel Career Snapshot: Tour Director

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This post was originally published on March 12, 2018 and last updated on March 11, 2021.

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Need some help planning your own road trip with your best friend? Full Life, Full Passport offers customized itinerary planning for all kinds of trips and budgets.

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