Travelling with others can be an amazing way to build memories — but let’s be honest, it also comes with its challenges. Over the years, I’ve picked up a few lessons (sometimes the hard way) about how to make group trips smoother and more enjoyable for everyone. Whether you’re the planner, the laid-back one, or somewhere in between, here are some things to keep in mind.

Be clear about expectations upfront — especially when it comes to budget. It can be really frustrating when someone agrees to a certain amount, then keeps adjusting it downward. If you’re the one planning, it puts you in a tough spot.

Set a realistic range from the start, and make sure everyone’s truly on board. It’s okay to ask:

“Are you sure you’re okay with this plan?”
This helps avoid resentment later and creates space for people to speak up if they’re unsure.

When I’m planning a trip, I like to make sure everyone is really okay with the plan because I want them to enjoy the trip too. But I won’t know if they aren’t responsive — and that can lead to confusion or disappointment later on.

If you’re travelling with others, please reply promptly to messages and questions about plans or changes. Even a quick “Sounds good!” or “I’m okay with this” helps keep things moving smoothly.

Good communication upfront saves a lot of headaches down the road.

Not everyone moves at the same pace or wants to see the same things. I’ve learned to adjust my plans depending on who I’m with. If someone needs more rest or slower mornings, I’ll ease up on the itinerary.

But that doesn’t mean you should cater everything around others. Be open to splitting up for parts of the day — it’s totally fine to do your own thing sometimes. You might even stumble upon something unexpectedly special.

And remember: just because you’ve travelled well with someone before doesn’t mean it’ll always be the same. People change. Travel styles shift. And sometimes, you might realize you’re not compatible travel buddies — even if you’re great friends.

Coming from an accounting background, I highly recommend tracking expenses as you go — don’t wait until the end of the trip when things get fuzzy. I use Splitwise, which helps keep everything transparent and fair.

Try to key in costs during a break or right after a purchase, and remind each other to do the same. You don’t want to end up forgetting that ice cream or taxi ride — it adds up!

And if you’re the one paying for most things upfront, don’t feel like you need to handle all the tracking yourself. Others should chip in by helping to log expenses too, not just leave it all to the person who footed the bill. A little teamwork goes a long way — and it prevents awkward money conversations later.

When I travel with my mom, she helps to key in expenses even if I’m the one paying — and I honestly really appreciate it. It lightens the load and is one less thing I have to do. It’s a small act, but it shows we’re in it together.

If you naturally take the lead in organizing — great! But if you have strong opinions or high expectations, be mindful of how you respond to other people’s ideas.

I’m guilty of this myself — sometimes I reject suggestions or change plans without much discussion. But I’ve learned that doing this can make others stop offering input altogether, which builds quiet frustration.

So if you want control, own it — but also be kind. If you’re open to sharing the load, divide up tasks like transport, meals, or daily routes.

Not everyone has the same planning style, and that’s okay. But don’t discredit what others can contribute, even if they’re not the “planner type.” Some people are great at spotting things you might miss, asking questions, or staying calm in tough situations.

Let’s be real: disagreements are bound to happen. People are tired, hungry, or stressed. That doesn’t give anyone a pass to snap or lash out.

If something’s bothering you, talk about it — but not in anger. Otherwise, people get defensive and can’t hear your side. And some people might still not understand where you’re coming from, and that’s okay too. If it becomes a pattern, maybe they’re not the best person for future trips.

The key is to be honest and kind. Don’t bottle things up, but also don’t unload in a way that hurts others.

Even if someone’s help doesn’t meet your planning standards, try to be thankful they tried. If you keep dismissing their efforts, they’ll stop offering — and then you can’t be upset when they don’t help.

Group trips aren’t just about the sights — they’re about how you navigate together. So learn to accept a bit of imbalance, and be okay carrying more of the load sometimes. It’s all part of the experience.

Travelling with others will always come with ups and downs, but with the right mindset — clear communication, flexibility, and a bit of grace — it can be incredibly rewarding. You grow not just as a traveller, but as a person.