Photo by Caleb Zahnd.

Even if you’re the kind of person that enjoys traveling on your own, it’s pretty much inevitable that at some point you’ll end up taking a vacation with friends or family members. That’s the kind of thing that can seem like a great idea when you’re back at home, the office, or at school, excitedly planning your escape – but once you’re on the road, a lot of things can go wrong. Many traveling companions end up bickering over every little thing, some have massive fights, and a handful even destroy their relationship for good.

Fortunately, all of those things are preventable, and it’s completely possible to travel with friends or family and have a great time – as long as you put in a little forethought. In my opinion, the two main issues that people fight over when traveling are money and how to spend their time, so let’s break those things down and take a closer look.

How to spend your time

It might sound obvious, but the reason people fight about how to spend their vacation time is because they had different interests and expectations in the first place. This means that if you want your vacation to go smoothly, the single most important thing you can do is choose a traveling partner you’re compatible with. This is actually more complicated than it sounds, since people that seem as if they’d be compatible might not actually be – just because you get along with a coworker in an office environment or a friend in a school setting doesn’t mean you’ll get along once you’re both thrown into a foreign setting.

Here are three key questions you need to ask yourselves before setting off together:

1. Do you have similar comfort levels? Some people like traveling on rickety old buses, eating at street stalls and engaging in more adventurous activities, whereas others require more amenities, nice restaurants and luxurious hotels in order to enjoy themselves. If both of you don’t fall into the same category, one of you will likely end up miserable.

2. Do you have the same travel goals? Some people like to spend all day visiting museums and tourist attractions, and some would rather party all night and sleep all day. It’s certainly possible to do a bit of both, but make sure you and your friend agree on how you plan on dividing up your time.

3. Do you and your partner have the same financial attitude? In other words, are you hoping to have a budget holiday or an indulgent vacation? Again, it’s important to be on the same page.

If for whatever reason you can’t choose your travel partner, then compensate by choosing your destination carefully. For example, a beach vacation is fairly straightforward – there’s hopefully not a lot that you would find to fight about.

Another crucial measure is to avoid traveling with a really large group.  It simply takes too long to reach decisions between so many people and a lot of valuable travel time can be wasted arguing. However, if you must travel in a pack, consider a beach holiday, a cruise or an organized tour, since a more structured vacation will leave less opportunity for fights.

Finally, remember that once you’re on vacation, you and your companion can always spend your day apart. If you can’t agree on what to do that day, there’s no reason that one person couldn’t go shopping for souvenirs while the other goes to visit an art gallery. It’s easy to get annoyed with someone when you’re together 24/7, but spend some time apart, and you’ll likely miss each other enough to remember why you wanted to travel together in the first place.


The easiest way to avoid fights over money is by establishing a shared wallet. How this works is that each friend puts an equal amount of cash into a wallet that will be used to pay for joint expenses, for example, accommodation, museum tickets, taxi fares and so on. Each person continues to “top up” the shared wallet with an equal amount of money as needed (and whatever is left over at the end of the trip can be divided up evenly and returned to each traveler). If one of the friends ever wants to make a personal purchase (e.g. souvenirs), they dip into their personal wallet.

This method works well because it’s much easier than each person paying separately for everything and trying to reconcile the differences later – unless you happen to be an exceptional record keeper. People get upset when they feel they’re being short-changed, so knowing that everyone is contributing their fair share can keep fights at bay.

Again, remember that if you pick a travel partner with similar financial values and spending style to you, you’re less likely to end up in an argument over cash.

What do you think? Have you had any particularly bad experiences traveling with a friend? What lessons can you share?