Tips for Traveling with Friends & Family: Santorini, Greece

12 Mistakes to Avoid When Traveling with Friends

Nick and I have been on the road since October of 2016. And prior to that, we took a big trip for 15 months back in 2013. We’ve had a lot of people come to visit – parents, siblings, and friends. Generally, all of the visits have gone relatively smoothly, but we’ve had a few hiccups along the way. And we’ve learned some valuable lessons about traveling with friends over the years.

Check out the following list of things to avoid when traveling with friends and family!

12 Mistakes to Avoid When Traveling With Friends

1. Expecting one Person to Plan Everything

Tips for Traveling with Friends & Family: Gili Islands, Indonesia

We’ve had multiple people visit us over the years and it’s usually the same story. They want us to book the hotels, plan the activities, organize transportation, and do all of the research ahead of time. We totally understand that the expectation is there because they have regular jobs that keep them busy, and we don’t. We travel all the time and they don’t.

But what people don’t realize is just how stressful it is to plan someone else’s vacation. We spend hours looking at hotels and reading reviews to ensure that everything will be perfect. We pour over blog posts so we can maximize their time in a country and make sure they get to see all the highlights. We pre-book all of our hotels and flights so that we get the best prices. We try to make everything absolutely perfect.

But things don’t always go as planned. Buses are late, hotels aren’t always as good as they seem, it might rain, and we might get ripped off. And because one person has done all the planning, only one person feels all the responsibility. And guilt. It is too much pressure to put on one person. Unless it is their job and you are paying them (you know, like a Travel Agent).

Read blogs to figure out the best things to do in the country you’re visiting. I promise that you’ll enjoy yourself more if you’ve invested some time in the planning process. Plus, you’ll have an idea of the things you really want to see, and the things that you don’t care so much about.

2. Not Communicating your Budget

Tips for Traveling with Friends & Family: Mykonos, Greece

When it’s just the two of us, Nick and I generally try to stay in basic accommodations that cost about $25/night. We eat at local joints and often take buses instead of taxis to save some dough. Our goal is to stick to a budget of no more than $50 per person per day, but preferably just $50 between the two of us.

So when friends come to visit and say “oh, just book whatever hotel you’d normally book for yourselves” I laugh a little. Because if you’re flying across the world for a two-week vacation, I’m guessing you want a hot shower and a comfortable bed (luxuries that we don’t always have).

But how am I supposed to know if you really just want to spend $25/night, or if you want to spend $100? Or $200? Should I be booking a stay at the Four Seasons or do you want a bunk bed at a hostel? And would you rather travel by plane, or save a few dollars and take the train?

Set a daily budget for yourself, and communicate it with your travel buddies so that you’re all on the same page. And if one person has a huge budget and one doesn’t, you should discuss the possibility of staying in different hotels or booking different activities.

Unless you’re a billionaire, in which case you can just pay for everything (and invite me to tag along)!

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3. Not Creating a Money Strategy

Tips for Traveling with Friends & Family: My Son Ruins, Vietnam

It’s not necessarily easy to get split checks depending on where you are traveling with friends. And charging different amounts on different credit cards is virtually out of the question. So you’ll need to devise a plan for how to pay for things. Should you all get cash out and divide the check evenly? Should people take turns paying? Should one person pay and send Venmo requests to everyone else?

Whatever you choose, be sure you’re being fair and not leaving the responsibility up to just one person. If just one person is paying for everything, tracking everyone’s expenditures, giving you money for individual shopping expenses, and sending out the Venmo requests, they’ll probably feel like they got the short end of the stick. Especially if they have to remind you to pay your bills.

Everyone in the group should have cash on them at all times to pay for their own drinks, snacks, or souvenirs. And if one person is footing the bill and tracking for everyone else, be sure to pay your Venmo requests promptly so they don’t have to be the group nag.

4. Not Doing Your Research

Tips for Traveling with Friends & Family: Bonneville Salt Flats, Utah

Do you know how to get a visa? What is the currency exchange rate? Do you need to dress conservatively? Is English widely spoken? Can you get Wi-Fi or a SIM card when you land? How to get from the airport to your hotel?

And aside from the research basics, have you done any research about things that you want to do while you are visiting the country? And if not, why are you spending all of this time and money to visit a place that you know nothing about? There must have been something that compelled you to book that ticket.

If you choose not to do any research about your vacation destination, fingers crossed that you are traveling with a very patient friend who will pick you up at the airport and lead you to all of the places you will be visiting. If you don’t, you will probably feel incredibly overwhelmed as soon as you walk out of the airport.

Just like you shouldn’t count on someone else to plan your entire vacation, you also shouldn’t count on them to know everything. Going to Egypt? There are countless articles like “Things to Know Before Visiting Egypt“, “What to Pack for Egypt“, and “A Complete Guide to the Great Pyramids“. Granted, you can’t prepare for everything, but you should put the effort in to at least know the basics.

Or at least read my blog titled 62 Essential Tips for First Time Travelers so you’re ready for anything and everything!

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5. Not Getting on the Same Page Regarding Time Versus Money

Tips for Traveling with Friends & Family: Sahara Desert, Morocco

What is more valuable? Your time? Or your money? If you’re short on time and want to make the most of it, regardless of the cost, then communicate that with your friends. It will probably make more sense to travel by plane than by train, and by taxi than by bus. It will be more expensive but will increase the amount of time that you have to do other things.

If money is more valuable than time, you’ll want to communicate that as well. You may choose to walk a mile to the beach rather than take a cab. Or you might take that overnight train ride to save on plane fare and the cost of a night in a hotel. It’ll take longer but will save you a bit of money.

If one person values time over money and another doesn’t, you’ll probably run into some challenges along the way.

6. Not Taking any Alone Time

Tips for Traveling with Friends & Family: Bathtube Drinks

Remember when you lived in the dorms and you got in a fight with your roommate so you used a roll of tape to split your room in half? And if your roommate crossed the tape line to your side, there was hell to pay? Traveling with friends can feel like that sometimes. Especially if you are sharing a room and spending 24 hours a day, 7 days a week together.

If you’ve followed my list of things NOT to do up to this point, you’ve done your research, you know what you want to do while you’re on vacation, and you don’t actually need your friend to do those things. So take a day and explore on your own! It’s difficult to explain the sense of exhilaration and freedom that comes from being on your own in another country until you’ve actually done it.

Plus, when you meet up with your friend for a drink later, think of all the stories you’ll have to share about your day!

7. Sharing a Room

Tips for Traveling with Friends & Family: Kenting National Park, Taiwan

Speaking of alone time, if you’re over the age of 25 you’ll probably be much happier in your own room. You won’t have to share a bathroom, you won’t have to hear someone else snoring, and you’ll have some quality time to yourself. It’s worth the extra cost, I promise.

8. Not Pulling Your Own Weight

Tips for Traveling with Friends & Family: El Nido, Philippines

Staying in an Airbnb? Do your own dishes. Did you rent a car? Everyone should take a turn driving. Out of booze? Take your turn going on a beer run. Did your friend buy the last round of drinks? Now it’s your turn.

Using your travel inexperience as an excuse not to do the normal things that you do back home isn’t fair to everyone else you’re with. And you’re probably used to doing all of these things in your normal daily life anyway, doing them in another country isn’t scary. Unless you’re trying to drive a car in SE Asia, that’s horrifying.

9. Having a “My Way or the Highway” Attitude

Tips for Traveling with Friends & Family: Bagan, Myanmar

Yes, it is your vacation. But no, that doesn’t mean that you are going to always get your way. Your friend may choose a restaurant that you don’t feel like eating at, or maybe you want to do out dancing but they want to go home. Compromise. Or refer to the paragraph above and do your own thing.

It’s next to impossible for everyone to feel like they are doing exactly what they want to be doing when vacationing in a group. Inevitably, at least one person is always compromising.

10. Being in a Bad Mood

Tips for Traveling with Friends & Family: Santorini, Greece

I know, I know, you can’t be in a good mood ALL of the time. But you can recognize when you’re being a brat and change your behavior. Usually, people get in a bad mood while on vacation for a few reasons – they are jet-lagged, they are doing too much every day and are exhausted, or they don’t feel like they have a say in the group.

If you’re feeling moody, don’t take it out on your traveling companions. They haven’t done anything wrong. Tell them that you’re in a cranky mood and take some alone time or a nap. No need to drag everyone else down too.

11. Not Voicing Your Opinion

Tips for Traveling with Friends & Family: Pyramids, Egypt

Another common misconception that people often have about traveling with friends is that the best way to “go with the flow” is not to have an opinion. The planner may give some hotel or restaurant options to choose from and you think that saying “I don’t care, whatever you want to do” is the best response.

But we all do have opinions, even if we don’t vocalize them. And your friend has already done the hard part by researching and giving you the best options. The only way to really “go with the flow” is to just pick one. Even if you truly don’t care, pretend like you do.

When we are traveling with friends, we have a few methods to force decisions when necessary. The first is designating each day as a specific person’s “decision day”. That means that of the options that are presented throughout the day, their decision is final. The other is having everyone list their top 2 or 3 things to do in a city. Whether it’s an activity, a bar, or a restaurant, we make sure that we do them all.

12. Not Communicating

Tips for Traveling with Friends & Family: Oktoberfest in Munich, Germany

There is one overarching theme to everything in this post – COMMUNICATION IS KEY! Communicate your budget, talk about things you want to do while on vacation, and let your friends know if you are feeling too busy at work to do the appropriate amount of research or planning. If you don’t like the hotel that they suggest, say so! If you think they are choosing activities that you won’t enjoy, tell them!

Even if you make every single mistake that I’ve listed above, all is not lost. Take your friend out to dinner on your last night of vacation and tell them how much you appreciate them and how much you’ve enjoyed your vacation. Apologize if you’ve been moody or cranky or difficult. End on a high note and then do it all over again next year.

Am I missing any common mistakes when traveling with friends? Comment below so I can add them to the list!

Need some inspiration to plan a trip? Check out our favorite bucket list travel books!


Mistakes to Avoid While Traveling with Friends on Pinterest

About the Author:

  • Valerie Wheatley

    Val grew up in Portland, Oregon but moved to Oahu on a whim back in 2013. She sold her house and all of her belongings and bought a one-way ticket. Since then she’s taken two around-the-world trips and has visited 60-ish countries while living out of a duffel bag.

    Val started documenting the Wandering Wheatleys travels back in 2013 as a way to update friends and family about her whereabouts and to relay humorous daily interactions. The only readers were her mom and her mother-in-law but that didn’t stop her!

    These days you’ll find Val dreaming up future trips, creating new travel content, managing a team of amazing travel enthusiasts, and chasing around her two adorable but naughty kids.

3 thoughts on “12 Mistakes to Avoid When Traveling with Friends”

  1. Everyone who’s traveling with friends needs to read this and heed its awesome, helpful advice! Great and necessary article!

  2. Just went through so many of these pitfalls on a trip with my partner and four others. We don’t get to travel much and before we left we were talking about the day trips we wanted to take and all the food we wanted to eat. When we arrived, there was a shift to our group suddenly saying they were content to sit at the pool because they’ve been to the destination so many times and they’d rather just cook. Or if we eat out, the folks who have really strict food preferences don’t make an effort to research a restaurant with something they’d like to eat. Communication probably would’ve saved us the headache, but I think it’s also been a good lesson for me that travelling with a group just isn’t for me. Waiting around for people to get themselves together, or listening to people gripe when they were “fine with whatever” an hour ago… not how I want to spend my precious time away!

  3. I’m just coming off a bad experience travelling with some family. I wish I had sent them this article beforehand.

    I was left to plan every.single.thing, including the itinerary, hotels, flights, activities, restaurants, etc.

    I was the only one with data on my phone, so I did all the searching and navigating. I would try asking about what they wanted to do and provide options, but mostly get zero input. One person was at least appreciative, the other just started pulling an attitude a few days in, being difficult and moody for no apparent reason, and doing that passive aggressive thing of wanting us to know they were mad about *something*, but refusing to discuss it.

    Time apart was not an option, since they had made themselves entirely dependant on me.

    In the midst of this, when I mentioned that I didn’t want them to feel that they were essentially just following me around, and that I was trying to tailor the trip to what they wanted, they responded with “I don’t have a choice, how would I know what to do? I haven’t been here before”. When they did express an interest in something, I would research and make it happen, and even then they would often just change their minds and complain, even though we were doing exactly what they said they wanted.

    Any tips on identifying who may be a problem next time before committing to a trip? I think I’ll be reluctant to travel with anyone new in the future after this one. I took a lot of vacation time for this, and spent a lot of time and energy trying to plan something to make this a trip of a lifetime – with seemingly zero appreciation. So disappointing.

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