How To Travel With Your Best Friend

by Brenna Holeman


Machu Picchu, Peru

I write a lot about solo travel, because I’m often a solo traveller. There’s one person I can always travel with, though, and have an incredible time: my best friend, Kerri.


Seoul, South Korea

Kerri and I met in university in Halifax, Canada. Although we shared a few classes together throughout the years, it was only in our final year that we discovered how well we got along, and that we had a shared love for travel. We were both planning backpacking trips around Europe after graduation, and so we’d sit in cafes and pore over guidebooks, plotting our routes and our hostels and our modes of transportation. Despite our planning, we never actually crossed paths in Europe.


Brasov, Romania

Our friendship really blossomed through email, and, eventually, over Skype, although there were a few shared months in Toronto, too. Our first trip together was to Romania, Bulgaria, and Turkey in 2008; then, she came to visit me twice in Osaka in 2009. We then travelled through Thailand and Myanmar together in 2011, and I went to Seoul to visit her. Finally, in 2012, we travelled through Nicaragua, Costa Rica, Panama, Colombia, Ecuador, Peru, Bolivia, Chile, Argentina, and Uruguay. Throughout the years, we’ve also had lots of visits whenever we both happened to be in Canada. That’s 18 countries together. That’s a lot of laughs, and a lot of great moments, but it’s also a lot of tears and a lot of hardships. Travelling together can be one of the most difficult challenges your friendship will face, but, if you follow these tips, you’ll ultimately become even better friends, and closer than ever before.


San Blas Islands, Panama

So, how can you travel with your best friend… and still manage to be best friends at the end of it?


1. Before you even set off, make sure you’ve discussed your goals and your intentions for the trip. You need to make sure that you’re on the same page (or at least in the same chapter) when it comes to pace of travel, your budget, and the kinds of activities you’d like to do. If, for example, one of you envisions a luxury hotel getaway while the other wants a back-to-basics, let’s-rough-it camping trip, the two of you probably shouldn’t be travelling together, or at least need to have a serious chat. It’s not enough to say, “Let’s do Southeast Asia together!” You need to discuss your standards of accommodation, transportation, sightseeing, and spending. Better to discuss what each of you wants out of the trip before it even becomes an issue.


Medellin, Colombia

2. Share all of the pre-trip responsibilities. Talk often about what you’re doing before the trip: buying insurance, applying for visas, etc. Keep each other updated; nothing’s worse than realizing an argument could have been prevented if you’d only communicated properly. If you know you’ll be travelling together, you can also pack accordingly. When travelling around Central and South America, for example, I brought the guidebooks. Kerri brought the sunscreen and the GoPro. We rarely spent time apart from each other, so it was natural to share these things.


 Toronto, Canada

3. Develop a buddy system. It sounds incredibly cheesy, but it will help you both stay on top of things. Check with each other that you have your passports, that you’ve locked up the hostel safe, that your camera battery is charged, and so on. Two brains are better than one, so take advantage of that.


La Paz, Bolivia

4. Keep track of spending. Kerri and I often paid for things on our own, or split bills, but inevitably there were times when I covered something or she covered something. We made sure to quickly pay the other back, or to write down what we owed as to not get confused in the future.


Cali, Colombia

5. Share all of the trip’s responsibilities, no matter how big or how small. One person shouldn’t always be the one to book flights, or find the hostel, or navigate a new city (unless one person really loves doing one of those things). The last thing you want to feel toward your travel partner is resentment. The only way to truly enjoy your travels together is if both parties feel equal, and that the travel responsibilities are balanced; take turns finding restaurants or figuring out how to buy train tickets, or better yet, do it all together. You’ll both learn a lot, and you’ll be thankful for your friend’s opinion and advice.


Koh Phangan, Thailand

6. That being said, know when to take full responsibility. There will be times when your friend is, for whatever reason, unable to help out. Maybe she’s violently ill, or perhaps she’s lost her wallet and can’t take out cash. Now’s the time to actually be a best friend and step up to the plate. Kerri got a bit seasick when we sailed across the Caribbean, for example, and so I wasn’t going to complain that she wasn’t able to help me out with some of the chores we had on the boat. She got my back later on when I got food poisoning in Peru. One of the best parts of travelling with a best friend is always having someone to lend a helping hand.


Love the monk in the background: Rangoon, Myanmar

7. Always keep communicating. You have to be fully honest with each other. If your best friend wants to hike up a volcano or take surfing lessons or visit the newest art museum, and you don’t, speak up. You’re both adults; act accordingly. If your friend is doing something really annoying (if Kerri was a 5am plastic bag rustler I might not be writing such a glowing article), calmly tell him or her, and offer a solution.


Salento, Colombia

8. Know when to apologize. Sometimes, I can be a jerk. I know this, and Kerri knows this. If I haven’t eaten, I’m really hot, and we’re lost, I can snap at whoever happens to rub me the wrong way. It’s totally uncalled for, and it’s only happened a few times, but I’ve always looked back and admitted that I was wrong, because… I was. Apologizing doesn’t make you weak, it makes you a good friend. We all screw up and do stupid things, but it’s how we handle those things afterward that show our true colours. Don’t be stubborn, and learn from your mistakes.

Here’s a tip for travelling with anyone, not just your best friend. Never start an argument before asking yourselves: are we hungry? are we tired? are we uncomfortable in any way (too hot, too cold, sick)? are we lost? If you can answer yes to any of those, save the argument.


Olympos, Turkey

9. Compromise. I’m pretty sure that’s the key to every single successful relationship, but it’s hugely important if you are going to travel with your best friend. Kerri and I often talk about being soulmates – we are overjoyed to have found each other in life. That doesn’t mean we want to do all of the same things, though. What it does mean is that we are happy to compromise and to occasionally do something that one of us doesn’t necessarily want to do. We help each other out, and lean on each other. It’s a crucial part of being someone’s best friend.


Dressing up in Otavalo, Ecuador

10. Make other friends. Even though you have a built-in travel partner and friend, part of the beauty of travelling is to meet new people from around the world. Branch out! I might even argue that having your best friend with you means that you talk to even more people, as you’re extra confident. What’s the worst that can happen? You attempt to talk to a group and they act a bit cold (that’s happened to me exactly twice in 8 years, by the way)? You have your buddy to hang out with anyway, so no harm done. Kerri and I met a ridiculous amount of people together while on the road. We even wrote songs for some of them.

Another issue that might arise is if one of you meets someone you’d like to travel with as well, either another platonic friend or a romantic interest. That’s something that you and your best friend should discuss before you travel together, because you might have very different ideas as how to handle that situation. I know that, in the case of Kerri and I, we were very supportive of each other and totally respected that need to have some private time with someone else once in a while. Be happy for your friend, or open up to the possibility of travelling with someone new.


Bocas del Toro, Panama

11. Spend some time alone. OK – I have a confession. Kerri and I never, ever spend any time alone. Like, ever. We spent 5 months side by side in Central and South America, and, although we both always said that we were fine if the other person wanted to spend a day apart, we stayed together the whole time anyway. We joke that you could put us in an empty room, and, when you opened the door 24 hours later, we’d still be laughing. Not everyone’s like us, though, and sometimes a few days (or even a few hours) apart can do wonders. It’s also important to travel on your own from time to time – you learn a lot about yourself and are forced to be more confident, social, and resourceful. Recognize that travelling with someone 24/7 is very difficult, and be mature about the situation if one of you wants to spend some time solo.


Cali, Colombia

12. Don’t forget to have fun. At the end of the day, this is your best friend. Take silly photos. Laugh until you cry. Share everything, from your toothpaste to your innermost fears. Love her and compliment her and cherish every moment with her. Chances are, if you travel together well, you’ll be best friends for life.


Osaka, Japan

Travelling with your best friend can be an amazing experience, so long as you respect each other. While I love to travel solo, my best and most vivid travel memories are with Kerri – we get to share them with each other, and tell the stories again and again.


Near Uyuni, Bolivia

What about you? Have you ever travelled with your best friend? Did your friendship survive the journey? 


Check out Kerri’s blog here, her YouTube channel here, or add her to Twitter or Facebook.

You may also like


Emy October 28, 2013 - 1:29 pm

Once again I loved this post!

I have travelled solo only once, to Moscow two years ago. The experience wasn’t that good and I haven’t tried travelling solo again eventhough I’d love to. I just don’t feel confident enough to do it yet. Hopefully the time will come soon!
I am always traveling with friends or my sister. And in the first case, eventhough I love traveling with them, and it’s always been great experiences, lately there have been times when they definitely didn’t respect some of the points in this post. Everyone, including me, can get pretty annoying when hot/hungry or tired but I would say it’s pretty normal!
The one thing that really pisses me of sometimes is how quite often my friends have literaly no clue of what’s going on. They’re happy to go on a trip, but never will they talk about it first, search for the accomodation or try to look up what’s to be seen or done where we’re going. I often end up doing all of that alone and sure I love it, but I’d love it to be a mutual thing instead of a solitary one.

Rad October 28, 2013 - 4:57 pm

I traveled once in solo for one month in Japan, it’s a country I love so I thought that going for a solo trip will be the best way to enjoy it as much as I can.
I did like it, but it was not as good as I expected, being able to share some memories is very important during a trip.
I met many amazing people and made many friends during this month but I spent to some days wondering what I will do.
I think this month made me grow a lot, I learned about myself.

Last April, I went back to Japan for 2 weeks but this time with a friend, we moved a lot and enjoyed many cities and places and get to see the friends I made in my previous trip.
I loved the moments we shared together and will always remember the laugh we had.
A traveling buddy is very enjoyable.

Brenna Holeman October 28, 2013 - 6:54 pm

Interesting – there are only a few places that I’ve travelled to solo and then gone back with someone, and I think I had the same experience as you. While I love solo travel, there’s something about having a great travelling buddy to share it all with.

That being said, I also agree that those times alone really make you grow and learn a lot! Thanks for your comment.

Brenna Holeman October 28, 2013 - 6:52 pm

It is indeed very difficult when you travel with someone who isn’t on the same page as you. I found out how well I travelled with Kerri through trial and error – I travelled with a few people before her who I didn’t quite click with! Through the years, I’ve realised that I’d rather travel solo than travel with someone who doesn’t share my travel values. It’s a tough thing sometimes, but at the end of the day, it’s your trip and your memories.

I think you should try solo travel again…you might love it!

Linda February 26, 2014 - 9:37 pm

I have done this more than 40 years ago, but I did it alone. I spent 45 days in 17 countries, not bad way to start life. I had a job or I would have done this longer. I had taken a leave of absence cause I told my boss then in 1970 I had a meltdown and I needed time off, like 50 days. He said Sure without PAY though.. I agreed.

So I bought at that time Trans World Airlines and a Pan American Airline ticket to 17 different countries and also purchased at that time from NYS… a ticket that was called Euro-Pass for 375.for 60 days… and traveled all over Europe by myself.

I FEEL THIS … if you are single in college no husbands or wives. Every college teen or semi teen needs to do this… You find out who YOU REALLY ARE by living the life as a bag-a- bond adventurer.

I loved the places I seen.., I remember living in a tent in Switzerland with some people I met on a tour.. I was not on the tour they were older people but for some reason they adopted me for 2 whole days…

Some felt sorry gave me food and Free lodging. In Paris. France, I stayed in Amsterdam in alley ways in the summer there was no hotels available something to do with a tour groups ate up all the lodging there.

I went to Germany, Bavaria, Beligium, Greece, Litenstein,England, Spain, Portugal, and Northern Italy. Those were some of the countries. I stayed in various other places too, I can not recall all of them.. Turkey was my favorite… Istanbul… Africa, Isreal, I did this mostly by train. I ate my lunches for the main meal of the day carried lots of jars of peanut butter for protein if there was no meals were handy… I loved the people I met, drank lots of Italian wine and drank a lot of beer too… I came home 45 pounds fatter… that was good then now its not a good idea.

Well, I say to any young person out there… My entire trip with spending money in 1970 cost me 1100.00 that was a lot then but now todays standards… I think its best to find a family to take you in a working farm… We ( met people along the way that I helped stay at their homes for 1 week) and they housed me I mowed lawns, made bread, milked a cow and brought in eggs at 5:30 am which to me was my place to sleep I was on vacation.. so I thought. Then I had to come home after I ran out of money came home just in time to call Daddy come and get me at Kennedy Airport then the telephone booths were ten cents. Yep that’s right 10 cents for a phone call… they do not even exsist now but I had the best vacation in my life… Next I want to go to Bali, Thailand and Singapore, Hong Kong…. and visit some family in Austraila… I hope to go there… but this time I will bring my husband of 26 plus years, no children but I want to find what I missed the last time.. Have a glorious time and be good, careful watch your money and drink a lot of wine… it tastes like candy!!!

How To Travel With Your Best Friend | travelingking October 28, 2013 - 3:25 pm

[…] via How To Travel With Your Best Friend. […]

Sally October 28, 2013 - 11:32 pm

This is such a sweet post! And makes me wish I had a best friend to travel with… hah. Great tips, these could easily apply to romantic relationships too.

Brenna Holeman October 29, 2013 - 1:19 pm

Aw, thank you! I agree that the tips could really be applied to travelling with anyone – but I almost always travel with Kerri, so it made sense to focus on her. Plus, I wanted to post those photos, ha ha!

Expatkerri October 29, 2013 - 7:17 pm

Thank you for sharing our stories here Brenna! I am honoured to be your friend and to be your travel partner! You’re a wonderful travel mate, as you love to go with the flow and see where the days take us. Under the sea, in the jungle, on a mountain or in a little cafe, I’ll be there!

Brenna Holeman October 30, 2013 - 12:45 am

Yay! Here’s to our next amazing adventure together. x

The Night Train - This Battered Suitcase October 30, 2013 - 2:34 pm

[…] laugh would carry us through at least another dozen countries through the years. This was just the beginning of us, of our friendship and our […]

Zalie October 30, 2013 - 9:21 pm

Wonderful tips and sharing as always sister! I particularly agree when you said that you should not start an argument before you ask yourself if you are hungry, hot, tired etc… It is always far too easy for a fight to arise when under extreme conditions!

Brenna Holeman October 30, 2013 - 11:15 pm

Thanks, Zalie! I think we both know how easy it can be to start a fight over something tiny… especially if we haven’t eaten! 😉

Travel Bloggers of the Month October 2013 | The HostelBookers Blog October 31, 2013 - 10:14 am

[…] She’s got advice in spades: How To Travel With Your Best Friend […]

Christine November 5, 2013 - 11:33 pm

You are so lucky to have a best friend and a travel buddy! Wish I have a gf that I can travel with too. It’s not the same with my bf.

Amy November 7, 2013 - 10:11 am

Brilliant tips – especially the one about questioning whether you’re hungry/tired/sick etc before starting an argument. I travel with my boyfriend and we often fall into the trap of arguing when times get tough, I’d really like to break that cycle though.

Brenna Holeman November 7, 2013 - 12:05 pm

I think we all fall into that trap! I really try to think about why I’m feeling the way I am before starting a fight. It doesn’t always work, though………

Alyssa November 7, 2013 - 9:51 pm

Love these tips! My best friend and I both love to travel but 11 years later we’ve completely failed to ever leave the city together! Unless you count the grade 8 trip we took to Ottawa haha.

It’s awesome you have all of these shared experiences with Kerri. My ultimate plan is to visit Vanessa for Christmas in Colombia where she’s from. I don’t know how much that’ll be from London though!

Brenna Holeman November 8, 2013 - 2:27 pm

Thanks, Alyssa! I hope you get to travel with her soon. It really is a ton of fun to travel with your best friend.

Links I Like, week of 11/4 | Katka Travels November 8, 2013 - 2:00 pm

[…] How To Travel With Your Best Friend.  Love this breakdown by Brenna, who crafts beautiful words into sage advice and uses her own experiences traveling with her bestie. […]

Glamourous Traveller November 10, 2013 - 3:09 pm

Wonderful post! I do the same with my ‘magic’ friend. A friend that I only meet up once a year and only to travel. We keep in touch well the rest of the time but there’s something about the magic of travelling together that can easily keep you bonded for a long time after. As for us, we’re deff the type that needs a bit of time apart after travelling together for a long time. We always meet up together in the evening or night to catch up on our slightly different days though

Brenna Holeman November 10, 2013 - 9:22 pm

That’s so great that you have a friend you love to travel with! I totally agree about the “magic”.

The Single Honeymooner - This Battered Suitcase November 21, 2013 - 6:01 pm

[…] I met in Costa Rica was American, was part of a couple, and was recently married. I was with Kerri, and we knew that we didn’t have much time in the country, so we travelled quickly through […]

The Long Way Round - Taking Yangon's Circle Train - This Battered Suitcase January 6, 2014 - 9:05 am

[…] our third day in Yangon, my lifetime travel partner Kerri and I decided to join our new friends Uros and Jerome for a ride on the Circle Train. We had […]

Traveling With a Friend February 24, 2014 - 2:11 am

[…] THIS BATTERED SUITCASE Brenna is a travel writer from Winnipeg, Canada, who has been on the road since 2006. She doesn’t always travel with someone, but when she does it’s always with Kerri who has also been traveling or living as an expat since 2006. Their posts on their travels together are always good for a laugh, as well as giving excellent advice for how to have the best time when traveling with someone else. […]

Linda Jewelry Queen February 26, 2014 - 9:45 pm

I love this site, it allows you to share your ideas with others who have the similar to where you went. I think that most young people need to find out who they are by learn and experiencing other countries and ideas. Thanks for having this, since I have not traveled too much, went back to Italy 2 yrs ago, planning a next trip in 2016 to Europe and hopefully live or stay in a castle… for a few days… the money does not take you that far with what we all have now… we must change what we have and treat everyone the same way… I hope to, find new friends on here to share my life and experiences with.

thanks for a great website.

Sam June 27, 2014 - 5:13 pm

Heyy there, nice Brenna ! I loved this article ! I wondered if you could write a story about Kerri and you, your friendship, how you met, how you managed to keep in touch through the years… You two are so inspirational, it would be great to read it.
Lots of thank you for your blog, it is always a pleasure to read about your adventures.

Brenna Holeman June 27, 2014 - 9:34 pm

That’s a good idea… I will definitely consider it! Thanks for your nice comment.

Why It's Okay to Not Be a Solo Traveller - This Battered Suitcase November 28, 2014 - 1:32 am

[…] lot of my other favourite memories have taken place while travelling with someone, especially my best friend Kerri or my mum. I love that I can ring them up and chat for hours about our past travels, be it that […]

Hanna March 5, 2015 - 8:43 am

Hi Brenna! Your post is very helpful. My friend & I are planning a trip to Seoul, South Korea in Autumn. And I learned a lot from your tips so to speak. I hope that we’ll be able to make the best memories while traveling together. Thank you so much!

Brenna Holeman March 5, 2015 - 4:24 pm

That’s great to hear, thank you for letting me know! Have an amazing time with your friend.

Yuna August 2, 2015 - 2:15 am

Love this post because once or twice in a year, I love to travel with my bestfriends <3. We usually do 11 of 12 points here, especially the last point. 🙂

Brenna Holeman August 2, 2015 - 1:06 pm

Aw, that’s great! Thank you for sharing, Yuna.

The Benefits of Travelling While Single - This Battered Suitcase September 10, 2015 - 12:15 am

[…] butterflies. It’s also fun to sit on the top of a mountain and cuddle up to the one you love (sorry Kerri, in this case you don’t count). On the other hand (are you getting confused yet what with all the heads and the hands and the […]

David November 15, 2015 - 4:30 am

Hello! My best friend (and my kindred spirit) are going to iceland in the summer of 2018. We will be both 18 that year but we are wondering how exactly we should plan it. Do you have any tips for first time travelers going to a country such as iceland? Luckily flights from Canada to Iceland are really affordable, but we won’t be old enough to drive there yet… hehe… what are the steps to planning a trip? Thank you~ ^_^

How Do You Know You're Ready for Long-term Travel? - This Battered Suitcase December 1, 2015 - 5:14 am

[…] how are each of you going to contribute to the trip? (By the way, you can read more tips about travelling with your best friend here.) The sooner you take care of these loose ends, or things that may hold you back, the better […]

Brian March 31, 2016 - 10:36 am

These tips I like and wished I’d read years ago. I did a roadtrip to Philip Island (won’t go back, pretty sure the place is cursed) with two friends and our friendship, something we were so certain of went through hell. Things have been mended but I’ve been left more inclined to travel solo. I do get lonely, yes, but I value the freedom I’m awarded to.

CherylBean May 22, 2017 - 1:06 pm

Hello Brenna, Nice share.. These tips are just awesome. I love travelling with my best friends. I just loved your post. I and my best friend often go for adventure twice in a year or sometimes thrice as well. WE both love to explore new places and nature. Your post will help us in many ways. Keep blogging.

Rajat Kumar September 9, 2017 - 5:10 pm

I have always loved being solo on trips. Because the main motive of travelling is exploring and having a time of my own and there I am not looking for someone to intervene. But yes, I can’t deny the benefits of travelling with friends (specially when responsibilities are equally shared). It’s about freedom not burden.


Leave a Comment

This site uses Akismet to reduce spam. Learn how your comment data is processed.