There’s nothing quite like travelling with a close friend to shine a bright (sometimes unflattering) light on your dynamic. It’s a bit like taking your friendship and running it through an obstacle course across borders, time zones and disagreements.
My best friend and I just returned from a trip through the East Coast of the US and Canada: From New York to Niagara Falls, Montreal to Washington DC, we packed a lot in and learned even more about each other in the process.
We’re still close (promise). But we definitely walked away with a deeper appreciation for each other and for the boundaries that kept us sane. These are the rules we discovered along the way.
1. Time apart is time well spent
Before we even left Australia, we agreed: it’s okay to take time apart.
We didn’t need to see every museum, café or street mural together and in fact, the days we split up often turned out to be the most enriching. While I explored the 9/11 Memorial Museum solo in NYC, my friend was out soaking in Brooklyn’s creative energy. In DC, we had wildly different tastes in Smithsonians, and that was fine. We’d regroup at dinner, swap stories and reconnect.
Rather than being a sign of disconnection, that time apart gave us space to be our full, curious selves. And the storytelling afterward? Honestly, it was half the fun.
2. Be honest about your budget
Money’s awkward but not talking about it is worse.
We laid out our rough budgets early on: how much we were comfortable spending on flights, accommodation, food, and activities. It helped us set expectations from the beginning. For example, I was keen to splurge on an exit row seat for our 15-hour flight home. My friend, less so. No resentment, no guilt, we just picked seats apart and respected each other’s choices.
Honesty about budget removed a lot of potential tension. It also helped us prioritise: spend big on things we both valued (hello, Niagara day trip) and save on things that didn’t matter as much.
3. Use planning tools (and accept that one of you might use them more)
We started with a shared Trello board. We had lists for flights, hotels, activities, and restaurant wishlists. It was incredibly helpful… for about two weeks. Then life got busy, and I ended up being the main inputter to Trello and that was okay.
We fell into our natural roles: I’m more detail-focused, and my friend is great at spontaneous adventure once we land. Instead of keeping score, we acknowledged our strengths and played to them. If one person ends up steering the itinerary, it’s not about control, it’s about contribution.
4. Talk about beds. Seriously.
One big bed, or two small ones? This came up often when selecting accomodation.
We weren’t precious about it. We’d share a bed if it made financial sense, but it was important to talk about comfort levels ahead of time. After a long day in sub-zero temps, there’d be nothing worse than passive-aggressively battling over the doona.
Also, hostel or hotel? We went with a mix: hotels and private room hostels. Being upfront about your preferences and your tolerance for noise, cleanliness, and privacy saves a lot of friction later.
5. Agree on the pace of the trip
Are you “cram in five museums before lunch” people? Or more “sip coffee and watch the world go by”?
Turns out, we were somewhere in the middle though I definitely leaned toward fast and full days, while my friend preferred a slow and steady approach. We worked it out by alternating high-energy and low-energy days and sometimes just splitting up for a morning or afternoon to do our own thing (see Rule #1).
Trying to drag someone through your perfect travel day when they’re not vibing is exhausting. Letting go of the need to be in sync all the time? That’s freeing.
6. Meals are sacred
We might not have seen every sight together, but we tried to eat together every day and this became our anchor.
Whether it was poutine in Montreal, tacos in Toronto or a quiet dinner in a Washington DC bistro, mealtimes gave us space to slow down, reconnect and reflect on our experiences. It became a soft ritual that kept us emotionally in step, even if the itinerary said otherwise.
7. Room time is shared time
Downtime in your accommodation is underrated. But it’s also when habits clash.
You may be a “bedtime scroller,” while your friend is a “lights-out, eyes-shut” person. Some might prefer unpacking; while your travel buddy prefers living out of a suitcase. These aren’t big things, but in a small room with no personal space, they can start to grate.
Our solution? Talk about it. No judgment, just awareness. Sometimes that meant taking a solo walk while the other recharged, or headphones in for a podcast so the other could nap.
8. Don’t upgrade without talking about it
This sounds petty, but when you’re booking a tonne flights in a month, it matters.
I really wanted to use my points for that exit row seat for our LA to Sydney flight. My friend didn’t in part because she has no issue sleeping in a standard seat. We talked about it, I booked the extra legroom and we both flew in peace. The key is transparency. A sneaky upgrade or hotel room change can create tension that’s easily avoided with a quick chat.
9. Be honest
If something’s bugging you, say so. Gently.
We had one moment where a small frustration turned into silence. Later that night, over dinner, we admitted we were both just worn out. That honesty dissolved the tension instantly.
Assume good intent. It’s easy to misread things when you’re jet-lagged and sleep-deprived. Honesty, spoken with kindness, is your best tool.
10. Celebrate the differences
This was the biggest takeaway: you don’t have to travel the same way to have an incredible trip together.
I wanted the United Nations tour. She wanted to wander Brooklyn. I was more about historical museums; she preferred cultural ones. We learned from each other, gave each other space and grew closer because of it.
Travel reveals things not just about the world, but about people. The quirks, strengths and surprises. Sharing that journey is its own kind of adventure.
11. Trust matters especially when it’s complicated
This one’s a little more personal.
As a bisexual guy travelling with a female best friend, there were layers. We’ve never dated, and never will but from the outside, it can look ambiguous. Not quite the “gay best friend” trope, not a romantic couple either. Somewhere in the middle: deeply platonic, deeply connected.
Before we left, we both made sure our people back home were comfortable with the dynamic. That meant open chats with my situationship and between her and her boyfriend, setting expectations and being clear about boundaries. No mixed messages. No emotional grey zones.
Trust was essential not just between us, but from anyone watching from afar. We’re not responsible for other people’s feelings, but we are responsible for clarity. When you’re halfway across the world, that peace of mind matters more than you might think.
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