Traveling (stress-free) with friends

Nothing is worse than traveling with one of your best friends and ending the trip thinking “never again”. Similar to the age-old piece of wisdom “don’t live with your friends,” traveling can be just as disastrous for your friendship. Traveling is so important to me, so I am very particular about with whom I travel.

Planning your trip is one of my favorite parts of traveling, but it can be hard work. Throw in different personalities, interests, comfort levels, and budgets and this can be almost impossible. Traveling with your friends can deepen your friendship and help you learn more about each other. They also may surprise you! There a few people I’ve traveled with that I’m very surprised by how well we get along. Vice versa is also true. I know which friends I can travel well with and those I know I would be annoyed with before we even left. This leads to my first tip:

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Pick your friends you travel with carefully. Not everyone travels well together. I am very lucky and have quite a few friends, but I know I cannot travel well with all of them. In all honesty, probably only a few of them lol. I know not everyone would enjoy traveling with me because I am go go go the entire time. I also love my alone time and have no problem doing things on my own. You don’t need to be perfectly aligned on every aspect of your trip, but if you have different ideas on how this trip should be before you depart, this may lead to some uncomfortable moments on your trip. Making sure your budget, interests, and personality are somewhat on the same page can help mitigate a lot of these issues up front.

For example, when my boyfriend and I went to Poland, I knew I was going to go to Auschwitz. He didn’t want to go on this trip. We were perfectly fine separating for a few hours. If you’re with a group who feels the need to stay together the entire time but one person wants to spend hours in a museum and you are not about that life, then that will lead to some annoyance when you’re on your 3rd hour at an art museum.

If you’re friends by now, you should know how the other handles stress in various scenarios. Do they buckle down and get through it? Do they have a meltdown? Do they give up? None are wrong, but if you’re a “get through it” person and your travel partner is a “meltdown person” there’s going to be some hurt feelings! I’m a mix of both but tend to have a meltdown while I’m getting through it. When you’re traveling, things will go wrong. You’ll miss a train, you’ll run low on money, you’ll ruin some clothing. That’s part of the joy of traveling and the joy of growing :)

Set expectations from the start. As soon as you decide you want to go on a trip with your friends, have a frank discussion with them as soon as possible. This will set the tone for the communication throughout your trip. Here are some things to discuss:

  • Budget- how much are you willing to spend on flights? Accommodations (hostels, airbnbs, or hotels)? Meals (street food, grocery and cook for yourself, or restaurants)? Do you want to do any excursions? What price range restaurants should you shoot for? Any additional transportation?

  • Travel style - Do you go go go? Do you want every hour planned out? Or do you want a chill vacation with nothing planned? Are you open to spontaneity? Do you want to go out every night until the bars closed or do you want to be in bed early each night? Do you want to start the day early each day or sleep in?

  • Together or independent - Are you open to splitting up and doing things on your own or do you want to stick together as a group?

  • Any hard nos - Do you have any hard nos on your trip; such as, strip clubs, “coffee shops,” etc. Discuss this ahead of time so you aren’t outside of your comfort zone on your trip.

Discuss finances EARLY. Money can cause a lot of issues with anyone, but when your friendship is in the mix, it can cause some resentment. Discuss on the front end how much you’re willing to spend on accommodations and food. Breaking this up into nightly rates or price per meal is easiest. Don’t forget to figure in taxes and fees into the accommodation portion of your budget. It may look cheaper to get an Airbnb, but figure in the taxes, fees, and risks and then do the same for a hotel or a hostel and discuss. Also discuss how you prioritize your spending. For me, I’d rather spend a little extra money on a hotel than on anything else. Discuss if you’d rather spend more money on food or shopping, transportation around the city (taxis vs ubers vs public transportation) or hotels, etc.

  • Within discussing finances, use the app Splitwise so everything is split and no one person is stuck with the majority of the bill and having to ask to be paid back.

Check refund policies. I have heard time and time again about a group of friends going on a trip. One person pays for the entire accommodation or all of the flights with their friends promising to pay them back. One by one the friends drop out of the trip and don’t pay their portion. Discuss what will happen if this were to happen within your group and be sure to check refund and cancellation policies before you book.

Book refundable hotels and tours as much as possible, and for anything nonrefundable, have each person book individually when you can. When you can’t, such as sharing the cost of a room, get payment upfront and be clear than any nonrefundable payments are just that: nonrefundable. Anyone who cancels at the last minute, will be out their share of the nonrefundable costs. 

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Start planning ASAP. Assuming you’ve picked your dates and destination, you need to start planning as soon as possible. The more people that are involved, the slower the planning process becomes. I tend to be the planner, but love feedback. On my trip to Europe with my friend, Ro, I created a shared Google sheet where I created a calendar and asked for her thoughts. Anything she wasn’t interested in doing, or thought we should change the schedule a bit, we did. If this is not your ideal way of traveling, discuss with your group how you like to plan your trip and things to do.

Choose your destination carefully. I usually get my cheap flight alerts from Scott’s Cheap Flights and send them to a friend with a “wanna go?” email or text lol. If you are not on Scott’s Cheap Flights, what are you even doing?! If you are and you still are planning to go somewhere where there hasn’t been a deal, then how do you decide where to go? Here are some options:

  • Have everyone write out their top 3 destinations. Any places with multiple votes or the most votes win. If they are in the same general area and you’re open to hopping around, do a multi-city trip! If none of the answers are the same, look at common factors. Are they all European cities? Are they all beaches or mountain towns? Do they have historical significance? Discuss why your top 3 choices are your top 3 choices and this can hopefully help narrow your choices.

  • Decide based on cheap airfare (usually what I do). If you get a cheap flight alert (like my $371 RT Memphis to Berlin), tell your friends to hop on it. The alerts usually are for a few months out so you’ll have plenty of time to plan.

  • If you’re all coming from different places, choose a destination that is realistic. If' you’re coming from all over the country, pick a place that is a similar distance from everyone so one person isn’t having to travel 8 hours while the others are traveling only 3.

Don’t be afraid to have alone time. It is unrealistic for your friends to expect you to want to be with them the entire time. Just like it is unrealistic for them to want to be with you the entire time. Don’t be afraid to set boundaries and have some alone time. If there is something you want to experience or do and no one else does, do it alone! Just be sure to set those expectations during the planning process so no feelings are hurt and no one is surprised. A little bit of space ensures you get to do everything you want, and it can help you appreciate your time together even more. 

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Don’t be afraid to be pushed out of your comfort zone a little bit. I feel I am a pretty adventurous traveler. But there are times where I am just dead tired and want to go to the hotel. Ro (and my boyfriend at home) both encouraged me to go to a club in Berlin one night when I was Queen Grump. I am so thankful for them pushing me to go out because it was an incredible time and also the last time we were in a group setting pre-COVID (so strange to think about now). There is a difference between not wanting to do something flat out, and not wanting to do something because you’re a little apprehensive. Allow your friends to encourage you and push you to do things that may be just outside of your comfort zone.





Traveling with friends can be a nightmare when it’s bad. When it’s good though, man, is it good.





Do you have any additional tips on how to travel with friends? If so, drop them in the comments below! :)

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