You really learn a lot about people when you travel with them. A trip can bring out the best — or the most chaotic — sides of everyone involved, so if it’s not planned right, things can go off the rails.
I was reminded of this recently on a trip to Scotland with friends, where I realized that so much of the experience starts long before the plane takes off.
From planning and packing to navigating new cities and making group decisions, every step of the journey takes patience, flexibility, and good communication.
Still, despite the stress, traveling together is one of the most rewarding ways to bond. When it’s done right, those shared challenges and spontaneous moments can create memories that last a lifetime.
Here are five things I would’ve done differently on a recent trip with friends.
Planning out logistics beforehand would’ve made everything run smoothly.
Early in the planning process, we started a shared PowerPoint to outline an itinerary and list everyone’s interests. However, we didn’t consistently update it, so by the time we left, it was only a partial list without details or scheduling.
As a result, many decisions were made on the spot — calling places from our Airbnb to make reservations or scrambling to buy tickets to Edinburgh Castle, which were sold out for two days in advance.
Next time, I’d use a shared document or spreadsheet to list everyone’s top three priorities, then map out out logistics and secure reservations and tickets to any must-see places.
I wish we had talked about a budget and set expectations early.
Traveling with others means navigating different budgets, interests, and priorities.
Some people may prefer spending money on rideshares for convenience, while others may want to splurge on fancy dinners or souvenirs.
For this trip, it wasn’t that we didn’t discuss this — it’s just that we only did it once we got to Scotland.
Setting a budget and expectations in advance would have made a significant difference and saved us from spending vacation time figuring out how to allocate our money.
We should’ve communicated a packing list so we didn’t show up with the same items.
When we all arrived at the Airbnb, we took inventory — three hairdryers, three curling irons, and so on. It turned out we were fully equipped to style the hair of all of Scotland.
Although we had plenty of tools to go around, it wasn’t really necessary. For shareable items like these, it would’ve been smart to coordinate ahead of time about who’s bringing what.
That way, we could’ve avoided duplicates and freed up packing space for other items.
It would’ve been smart to delegate responsibilities.
Thinking about it now, it would’ve been helpful to delegate responsibilities and have each person in the group take charge of something.
For example, one person could have been in charge of ordering Ubers, and another could’ve put their card down for dinners. This also works for non-monetary roles, such as having a designated picture taker or someone in charge of all navigation.
It takes the pressure off moments when someone needs to step up, keeps things running smoothly, and makes tracking expenses a lot easier.
Tracking expenses in real time would’ve made splitting costs way easier.
After the trip, my friends and I all had to comb through our bank statements to split shared costs and figure out who owed what.
It quickly became confusing — international charges were appearing under different names, addresses, and numbers, making it difficult to distinguish between them. It was also hard to identify which transactions had foreign fees attached.
Looking back, we should’ve tracked expenses in real time whenever someone put their card down. Apps like Splitwise or Settle Up make it easy to log purchases and divide costs fairly.
That way, nothing gets overlooked and no one ends up paying more than their share.
This story was originally published on January 21, 2026, and most recently updated on June 9, 2026.
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