In 2021, I spent 2 weeks on Hawaii’s Big Island with my best friend. Miraculously, we’re still best friends. I thought I knew a lot about traveling with others, based on my experiences with group and family travel, but traveling with a best friend held different challenges.
In this article, I will share with you advice for traveling with a friend that will help you avoid conflict, maximize enjoyment, and return home even closer than ever.
How to Avoid the Worst-case Scenario
The fact is, both best friends who travel together and couples do sometimes break up on a trip – and it’s not that uncommon!
Ask around in any hostel common room, and you’ll probably hear stories about people who arrived as inseparable pairs and departed with an absolute loathing for each other. These travel stories don’t make it onto Instagram and TikTok (although they occasionally make appearances on Reddit’s relationship advice forms 😬), but they do happen.
Thankfully, avoiding major conflict when traveling with a friend is reasonably easy to avoid.
Although I give more specific travel advice below, the basics of staying friends through a big trip boil down to these three things:
To travel with your best friend, you’ll need:
- good communication,
- good boundaries, and
Communication skills help us resolve conflict instead of escalating it. Good boundaries help us avoid conflict in the first place, and self-awareness helps us take ownership of our own actions (and apologize when it’s appropriate).
All these things add up to travel with friends that strengthen the relationship after we return home.
👭 How to Travel with a Friend without Conflict:
1. Don’t go with someone who doesn’t enjoy the same kind of travel you do
This might seem obvious, but plenty of best friend travelers have arrived at the destination with entirely different expectations for the trip!
When one friend assumes that “vacation” means endless days of lying on the beach doing nothing, and the other expects that “vacation” involves packed-full itineraries of things to do, it’s a setup for disappointment, conflict, and a big argument!
As you plan travel with your best friend, make sure that you are on the same page about the type of travel you’ll be doing.
Some things to communicate about include:
- 🏖️ Travel Style: a relaxing vacation, full days of sightseeing, or a little bit of both?
- 🏨 Accommodations: will lodging will be budget or luxury. Have you communicated about whether you will share a bedroom or bed?
- 🚌 Transportation: will you be taking ride shares or public transportation? Walking or relying on private cars?
While you both can navigate all of these issues even if there are differences in opinions, it can be a setup for conflict if your companion wants to sleep in and sunbathe on the beach while you ache to leave the resort and explore the region nearby. Make sure you agree on travel style, accommodations, and transportation – or reach an agreement about a split on time spent with each other versus doing things alone.
2. Don’t travel with a friend without an itinerary. Communicate about a plan
When solo traveling, it’s relatively easy to make spontaneous decisions and change plans on a whim. When traveling with a friend or friend groups, however, it’s important to have an itinerary.
Download my Printable Travel Planner
My vacation planner template is perfect for creating an itinerary that takes the input of many participants and meshes them together in a shared itinerary. Begin planning your trip today with this printable travel planning PDF designed for visual planners:
You and the friend you are traveling with should discuss booking reservations, handling various responsibilities, a complete packing list for the things you both want to do, and contingency plans if certain activities aren’t available.
A well-developed and collaboratively created itinerary is essential for successful travel with a friend.
3. Check in with each other regularly
When traveling with a friend, you’ll depend upon each other in ways that you usually don’t.
Away from your home, other friends, and family, you’ll become each other support system in a unique way. Not every friendship adjusts easily to this transition. One way to make it a little easier is by being very intentional about communicating.
One thing that caused conflict during my first time on a big trip with my best friend was a failure to communicate in advance about time spent solo. While my friend assumed I knew that she was going out for a walk while I showered, I emerged from the bathroom instantly concerned that she was missing! The conflict that ensued when she returned could have been easily avoided if we had both better communicated our expectations during the trip.
4. Remain aware of other people
You know that feeling when you are catching up with your best friend and no one else in the world matters? That totally oblivious-to-the-world mind-space where you’re just engrossed in being fun, silly, or playful with your bestie? It’s best to keep that in check on vacation together.
Yes, you are there to support one another and share the experience of travel with your best friend- BUT, it can be easy to be lulled into a false sense of security.
Remember two things:
- Stay aware of your surroundings always. Prevent travel crime and scams by being aware of people beyond your best friend.
- Follow the local norms and customs. Sometimes being with our best friend can tempt us to ignore local customs – like being obnoxiously loud on a train in Japan or dashing out of the hotel in Morocco in short shorts- while these things probably won’t be a danger to us, they’re disrespectful to those around us.
Avoid the temptation to think that “my friend is doing it, so it’s fine,” Instead, stay aware of your surroundings and follow the cues of those around you.
5. Stay in the moment, not on social media
Of course, updating your friends and family through a story or tweet is fine, and everyone expects a few Instagram posts during your travel, but live in the moment, not on your phone.
This is especially true when traveling with a friend. When you travel solo, it’s your choice if you want to spend hours glued to your phone – no one else will care. However, when you’re traveling with your best friend, it’s different. You are their person- their one familiar face and in-person contact. On a trip with a friend, try to minimize your phone time. Doing so can avoid conflict and help strengthen your relationship.
One study found that even having a phone upside down but visible on a table makes it more difficult to focus on a task or conversation! 1 So pack it away in a safe spot.
These days, when I travel with my best friend, we designate phone time. Perhaps because we are both therapists in our day job or possibly because we live thousands of miles away from each other now, we’re very intentional about this. However, when we travel together now we often say “I need some phone time now,” and take a break to check out. We have agreed, though, that during shared meals, phones go in our bags, not on the table.
6. Plan time apart
Spending time apart can be good for friends traveling together- especially on a longer trip.
Time spent alone helps introverts recharge. Days spent independently exploring gives you more to talk about when you meet back up for dinner!
If and when you separate, have plans and backup plans for how you’ll meet back up. While cell phones are an increasingly reliable way for travelers to communicate in international destinations, it’s not always guaranteed. Instead of simply saying “text me when you’re ready to meet back up,” always share a backup plan. Rather, Say to your best friend, “Text me when you want to meet back up, or if I don’t hear from you all see you at the restaurant at 7?” Without much effort, you can build in a backup plan so during travel with a friend you always know how to meet back up if separated.
7. No how, when, and what expenses will be split
Money can be a major source of arguments and hurt feelings when you are on a trip with a friend. Who is paying, how they’re paying, and when they’re paying can be a major headache.
Try and structure your travel so that money doesn’t have to be discussed constantly. If you communicate up front about “who, what, and when,” then you can relax and focus on the trip.
Paying for meals separately can often be the easiest way to split dining expenses. However, it’s less straightforward when it comes to shared costs like hotels, resort fees, and excursions purchased with a group discount.
While it can take a few moments to enter each transaction that needs to be split into an accounting app, it’s well worth it to avoid the conflicts, confusion, and resentment that can come from poorly managed money during travel with a friend.
8. Share Responsibilities
In every relationship – whether traveling as a couple or with a best friend – there’s a divide in responsibilities. Often, the “more responsible” person takes on more tasks related to planning, timekeeping, or managing transportation and lodging details.
Now, it is a good idea to plan travel with a friend by relying on each of your strengths. When I travel with my best friend, I handle the logistics of hotels, transportation, and bookings while she shines at researching attractions and pairing them with top-rated restaurants. However, when one person ends up doing more work to keep the trip on track, it can create resentment. When this resentment builds up, such as during multiple destination travel, it’s a recipe for conflict.
Instead, try to share responsibility evenly for creating and managing your itinerary and travel details. Or, at the very least, acknowledge the labor of the person working harder and make it up to them in some way.
Final thoughts on how to return home still best friends after traveling together
Traveling with a best friend will likely challenge your relationship in a way you may not have experienced before. Some relationships, under this pressure, may never quite be the same again. However, with good planning, boundaries, and communication, you can plan best friend travel that will strengthen your relationship and bring you and your best friend home even closer than ever.
What’s your take on vacationing with a friend? Have you tried it? What are your best tips for staying besties through the travel experience?
Artist, digital nomad, and highly sensitive person, Lynli started traveling full time as a digital nomad in 2018. Writer and Illustrator by day, remote-destination explorer by other-days, Lynli is passionate about pushing the boundaries of her own comfort zone, exploring the world as a plus size, one-bag traveler, and journaling it all on WanderBig.com