5 Tips for Travelling with Your Best Friend…and Staying Friends

If I had a dollar for every time someone warned me that travelling with a friend is the fastest way to end a friendship, I would be writing this blog post from Paris. Here’s the thing: Travelling with your best friend doesn’t mean the inevitable end of your friendship. Travelling your best friend accelerates your friendship. To travel with your best friend & stay friends, it’s important to make sure that your friendship is in a good place before the trip, that you can responsibly manage your own money, that you both are on the same page about your expectations for the trip and that you are quick to own up your mistakes & apologise, and likewise, quick to forgive. Finally, it is also easier to travel in a pair rather than a group of three.

Ultimately, if your friendship is meant to last, it will. Travelling together speeds up your friendship. If it was meant to eventually fade away (or blow up), it will blow up. Probably while you’re meant to be enjoying a gorgeous day in Milos or Paris or New York City, or wherever it is you worked so hard to travel to. Below, I’ve rounded up my top 5 tips for travelling with your best friend, and staying friends, based on years of experience of travelling with friends and my then boyfriend, now husband.

Travel with your Best Friend

My experiences travelling with my best friends

I’ve heard so many stories from friends who have hit rocky times on the road, with their friend, sibling or partner, that has left their relationship strained or permanently shattered. However, this is definitely not a reason not to travel together! I’ve taken long trips with a friend twice, the first time with a primary school friend and the second time with my lifelong best friend. I couldn’t have asked for better friends to travel with, and I’m forever grateful that they chose to spend their time & money overseas with me, and for being such patient, positive & fun travel companions.

While I’ve had great experiences travelling with friends, I’ve seen too many friendships and relationships take a hit while travelling. Pretty much every argument or resentment I’ve seen build, has been because of one of the issues I’ve detailed below. Travelling with friends or partners can be an amazing experience, and one that you’ll get to relive for years afterwards. With a few simple considerations, you can make the road much smoother.

Travel with your Best Friend

1. Don’t travel to make your relationship better. Travel to make it even better

Travelling with your best friend or partner can be really exciting, but it can also present some new challenges – especially if you don’t usually live together.

While travelling, I’ve witnessed a relationship breakdown that made the last two weeks of travelling awkward for one party, and heartbreaking for the other. I’ve witnessed so many friends lose their bestie after a two or three week trip of a lifetime, and ended their trip with tainted memories.

Travelling is an intense roller coaster of extreme highs and sudden, sometimes terrifying, lows. Before you book your tickets, you need to think about whether this person can see you at your best and worst (often in a matter of minutes) and still want to stick around. You also need to be able to do the same for them.

If you’re already on rocky ground or sense you’re drifting apart from your bestie, a big trip can seem like an amazing way to re-connect, but it’s likely a recipe for disaster.

Breakfast pastry in Paris

2. Manage your own money

Mixing friendships & money is rarely a good idea, but it’s an even more terrible one when you’re travelling. I’ve always travelled with friends who are really honest with money, and we always made sure we evened out everything by the end of the day.

It can be a little tedious, but when you’re travelling you often need to watch every dollar. Instead of becoming resentful about the croissant you shouted three weeks ago, the train tickets you bought last week and the drinks you shouted last night, take a few minutes to make sure you’re even every couple of days. If you’re finding that your friend who is conveniently in the shower every time it’s time to do a grocery run, you have two choices. You can let them know how much they owe you, and ask to sort it out that day, or you can let the problem grow, the tally get more complicated, and the awkwardness continue. It’s not ideal, but it’s better to raise it early than to let something fester. It’s much easier to do a money transfer or get cash out, than it is to take turns buying things of different value for each other – one person always feels that they’ve been shortchanged.

Naturally, make sure it’s not always you who doesn’t have their wallet out in time, or is in the bathroom when the bill arrives. Rather than suggesting it’s “easier” or faster for the other person to pay now, and you’ll work it out later, if you feel that way then put your card down and let them pay you back (at least the first time).

Blowing your budget early on not only impacts you, but it can limit your friend’s options too, if you’re sticking together. If you suddenly can’t afford the meals you’d planned or the activities you’ve booked, it leaves your friend in the difficult position of choosing to miss out on something for your sake, or to leave you behind and go it alone, and feel guilty about it. Unforseen circumstances are unavoidable, but blowing the trip’s spending money on a few big nights out in the first week or on a shopping spree is a choice that impacts both of you.

These days, it is SO easy to keep track of your spending overseas, because you’ll likely have wifi and a banking app. On my first trips with my friends, we had wifi nor an app for our travel card, so we had to manually keep track of our money. Despite some days of big spending, we both managed to stay in the black till the end of the trip. Success!

Travel with your Best Friend

3. Make sure you’re both on the same page

Before you travel, sit down and be really honest with each other about what sort of trip you’re both expecting and planning. Most importantly, this is discussing your budget and how you both want to spend your time. Make sure you’re on the same page about things like how much you want to party, how much you want to sightsee, and how much you want to have a planned itinerary vs going with the flow. If you’re not on the same page with these things, it will drive one or both of you nuts.

It doesn’t mean you have to do everything together, but you need to be comfortable going seperate ways if you know that one of you wants to sleep in & spend all day lounging by the beach, and the other wants a bit of beach time but is also happy to go and see a few sights by themselves.

Naturally, it often tends to be that one friend will be more responsible for planning, booking & knowing the itinerary. Make sure you’re okay with where you both sit in that dynamic, and find a way for the other person to contribute. Sometimes, being very happy to go with the flow is enough, if the planner is happy to do the research & planning, knowing that they’ll mostly be choosing what they want to do. It’s give & take, but it doesn’t need to be a very clear 50/50 split. Your unique dynamic should be what makes your friendship work, so lean into that! If you know that you’ll want to share some things around, speak up before you hit the road.

Travel with your Best Friend

4. Travel in twos, not threes (if possible).

When you’re travelling with your best friend, three can be a crowd. I can’t think of too many times I’ve been around people travelling in a group of three, that’s worked out all that well. A party of three makes for awkward power dynamics and extra personalities to manage. It can also mean when there is an argument, there’s one person awkwardly in the middle, who eventually has to pick a side (or train seat, or to go on the walking tour rather than the museum, etc).

If you’ve already booked a holiday with you and your two best buds, don’t freak out. You’ll most likely have an amazing time, especially if you go in knowing that a group of three can be a bit trickier to manage on the road. If you are holidaying in a group of three, take care to mix up who gets the mattress on the floor, the seat by themselves on the long train trip and who is calling the shots each day. Be conscious of not making one friend consistently the third wheel, or the (wo)man in the middle.

On the bright side, a third person can make it a little easier for one friend to tap out of an activity, have a quiet or moody day, and can lighten the load of the admin and planning.

Travel with your Best Friend

5. Own your mistakes. Forgive your friend.

This is easily the most important tip for travelling with your best friend and staying friends. Sometimes there is nothing harder than admitting you’re wrong, but it’s especially important when you’re living in someone’s lap for weeks or months at a time.

When you’re living in someone’s lap for weeks on end, it’s not the time to pretend your stubbornness or pride are endearing personality traits.  If you need to apologise, don’t waste another second of your precious holiday time skirting around the issue and pissing off your travel companions – spit it out!

Even if it’s as small as “Sorry I was a bit grumpy earlier, I was just a bit stressed about missing the train”, a little can go a long way towards preventing bigger problems.

When your friends are the ones screwing up, you need to let it go. As in, let it go and don’t bring it up again. Don’t spend a single precious second holding a grudge or being moody. The millions of happy memories you make will make up for it.

Travel with your Best Friend

What are your tips for keeping the peace?tips for travelling with your best friend

5 thoughts on “5 Tips for Travelling with Your Best Friend…and Staying Friends

  1. These are great tips and agree with you that they work whether you’re traveling with your significant other or your friend. I’ve experienced both sides of the coin- a friend that, while it didn’t end our friendship, I swore to myself I would never, ever travel with her again. And then I’ve had friends that I’ve actually become better friends with after the trip and we saw how much more we actually had in common. I think another tip is – don’t be afraid to spend a little time apart. Maybe your friend wants to shop while you head to the museum. No worries! You can both be happy.

  2. Love this! I recently went on a trip to New Mexico with two other colleague-friends, and I can completely relate to every single point you mentioned. 🙂

    Another tip: make an effort to split up jobs (e.g. in charge of airplane tickets, booking the hotel, getting directions around the city, etc.). That way, all of the burden won’t be just on one of the person.

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