A lot of people, when first starting out, feel much more comfortable with the idea of traveling with friends. I know I did. I had such a romantic idea in my head of climbing to the roof of the Florence Duomo with my backpack and my best friend. I imagined us roaming around Europe, going to parties, and making friends. In the end, life had different plans, and I went to Europe alone. I didn’t even climb the Duomo until 15 years later when I actually moved to Florence.
Since then I have spent months, adding up to years, traveling to dozens of countries by myself. Along the way, I have also had several chances to travel long distances with friends. Both are good, both are bad, and have different reasons why. Traveling with your bestie, or even a group of friends, can be super exciting. But you often don’t anticipate all the things that can go wrong and have the potential to change a friendship, sometimes forever. When traveling, your stress levels are higher, things are confusing, nothing works like it does at home.
So here I want to offer some tips on how to have a successful trip with your best pals, and not end the friendship over the equivalent of USD fifty cents.
1. KNOW YOURSELF
I know this sounds obvious, but it’s incredibly important. If you are unaware of your own needs and desires, you may find yourself resenting your friends for the smallest things- for meeting new people, for wanting to go out, for eating too much, for not eating enough.
It’s inevitable that you are going to figure this one out along the way, and it’s okay if who you are changes along the way too. The most important thing is to recognize your needs and wants, so you can communicate them to your travel buddy as you go.
Do you like going out? Do you wake up early? Stay up late? Need lots of down time to rest? Do you need lots of snacks? Do you hate museums? Do you drink? Do you smoke? Do you have social anxiety?
Start thinking about all the nuances of who you are and be ready to communicate with your friends about them. If you get nervous meeting new people, and your friend is outgoing, discuss what you can do so you’re both comfortable. You need to know yourself before expecting your friend to meet your needs, which can quickly lead to resentment while traveling.
2. DISCUSS IDEAS BEFORE YOU GO
This is exactly what it sounds like. Talk to your friend about what you hope the trip will be like, the things you want to see, and to do. Ideas you have. It’s important to set expectations before you leave, which can cut down on annoyances later. If you’re going to Paris and you’re hoping to rush around the city from the The Louvre to the Musée d’Orsay all day, but your friend was hoping to sit at a cafe drinking cafe au lait and stroll around Montmartre, there are going to be problems.
Having these discussions before you go can save you a lot of time, and help you to understand the other person much better. When I traveled with my friend Phoebe for 3 months overland from Asia to Europe, we got along great and our travel styles were in sync, though not perfectly matched. I liked to wake up early and go out to take photos in the mornings, while she slept in late. She might stay out later for a party with new friends, and I headed to bed early. This worked for us because we understood the other’s needs.
Here is a list of ideas you can discuss with your adventure buddy. Feel free to add any of your own that you feel are important:
1. What are the 3 most important things for you to do/see?
2. Do you want to go out at night? If so, where? Clubs? Bars? To see live music?
3. What time do you usually wake up? What time do you usually go to bed?
4. What will we do if our sleeping schedules are opposites?
5. Are you open to meeting new people?
6. Are you hoping to hook up with new people you meet?
7. If one of us hooks up with someone, what’s the plan?
8. Do you want to create a word, or action that means ‘get me out of here’?
9. How much do you eat during the day?
10. Do you eat breakfast? Do you need snacks all day?
11. How much money do you feel comfortable spending at meals?
12. Are you comfortable doing drugs?
13. Do you care about shopping? Do you want time to buy souvenirs?
14. Do you want to stay in a hostel? Hotel? Airbnb?
15. Which insecurities of yours do I need to be aware of?
16. Do you like to plan a lot ahead of time? Or just see what happens?
17. How can we share the responsibilities of making travel plans?
3. COMPROMISE & COMMUNICATE
After you have discussed all the above questions, and hopefully more, you’ll need to make some compromises; that will probably have become obvious while you were discussing them. You’re not the exact same person, but you respect each other, so how can you meet both (or all) of your needs for the trip. Your needs will also evolve once you get there, so keep the conversation going. Keep making fair compromises along the way. The key is to communicate.
Several years ago I went to Cuba with a good friend. I am a person who needs to eat often, or I get low blood sugar, and start to feel shaky. I did a very bad job at communicating this with my travel buddy. So as we walked around Havana, I kept asking my friend if she was hungry, and she kept saying no, so I kept saying ‘no problem, I’ll wait.’ But when dinner time finally came, it was several hours later, my brain wasn’t functioning and I snapped at her. This wasn’t fair to either one of us. Had I just explained that I needed a snack every few hours, she would have happily sat down at a cafe with me while I satisfied my blood sugar.
4. TAKE TIME ALONE
It’s easy to forget this. It’s easy to not do this. When you’re traveling, you’re often busy, seeing this museum, or eating at that restaurant, hanging out with the other people in the hostel, etc. But you need and should do this. Take a walk for 20 minutes, go to a cafe and write in your journal, go to the park and draw something, whatever you like to do, take time to do it. Alone. This can even be as simple as volunteering to go get the groceries by yourself this time. Taking time to yourself is like pushing a reset button. It gives you time to reflect, time to breathe, time to recalibrate. Even when you aren’t feeling any tension with your travel buddy, alone time will refresh you. If you and your pal are in a good habit of taking daily alone time, you have the potential to prevent any ill will or resentment before it ever starts, and that is the main goal
Asking for alone time should also not be taken personal. If your friend wants to take a walk alone, don’t worry, this isn’t about you, it’s about them and their self care. Build this into your schedule. You may not be able to do it every day, but you should definitely make it a priority on the days you can. Doing things alone while traveling can also build your confidence. If you’re reading this before you go, you may be rolling your eyes and thinking how silly it sounds. But trust me, when you’re there, in the moment, and the travel stress is building, you’ll know what I mean. Take time alone for yourself, and for your friendship
5. DOWNLOAD A MONEY APP
I started traveling long before money apps existed. A lot of the time I was alone, so keeping track of expenses wasn’t that big of a deal. But traveling with friends, money can create a lot of tension. When you’re operating in a different currency, a few US cents can start to feel like a lot.
You may pay individually most of the time, but there will definitely come a moment when only one of you has the exact amount of change, when you’re in a hurry and only one person has time to pay. Money will start to get mixed up, and inevitably, money resentment starts to build, no matter how small. It’s hard to keep track of- I bought you that water bottle, and you paid the taxi driver, and I paid for the bus tickets… it’s a lot.
I know people who have ended friendships after traveling together, over what added up to a few cents in the end. I myself have had travel conflicts and misunderstandings over money that put a black cloud over the entire trip. Don’t add this extra stress to your life, and download a money app.
There are several out there, but the one I prefer to use is Splitwise (this is not an ad). The app allows you to create groups for trips (or even house expenses, or anything else in life) and you can add in as many people necessary. You can add each expense in the app, say if it’s split evenly between everyone, or choose specifically who owes what. You can even choose which currency you want to use. If you enter every item into the app, you don’t have to keep track in your mind, and there will be less chances for resentments to build, knowing the app is doing the math in the background.
I have used Splitwise on several trips over several years, and it has saved me so many times. It’s one less thing I need to worry about while traveling.
6. CHECK-IN DAILY
Check in with each other at the end of the day, or at breakfast in the morning. Talk about how the day went, highs and lows, inspirations and frustrations. Talk about what you have seen, how it’s different from home. If you’re feeling stressed, if you’re feeling excited. If you met someone new. If you want to see them again. If you don’t want to see them again. Intentional daily check-ins with your travel buddy will keep you connected, and on the same page. They’ll keep any stress or resentment continuing over long periods of time. Talk about what you will do that day, where you want to eat, and if they hurt your feelings. Or if they did something kind. Be open to what your friend says even if it hurts; they’re only telling you because they value your friendship.
Checking in with each other will help you to leave the trip even stronger than when you first took off. Too many friendships suffer after a trip together, so take the steps to prevent that.