Ask These 5 Questions Before Traveling With A Friend For The First Time

From Girl's Trip, Crossroads, to the Sex and The City movies — the "girlfriends on a vacation" storyline is a reoccurring one in pop culture. On the surface, these group adventures look pretty simple to achieve: Get a group of friends together, hit the road, and good times will ensue.

In reality, going on a vacation with your friends can be a lot more complicated than that. Sharing a room with a friend will expose you to new aspects of her personalities and habits — and you won't always see eye to eye. Travel decisions can potentially turn into a landmine that hurts your friendship, from disagreeing on where to eat breakfast to how much time it takes to get ready in the morning.

To prevent a potential falling out, you should do your due diligence and suss out the proclivities of this person you'd be seeing a lot of for the entire trip. Click ahead for five smart questions to ask yourself — and your BFFs — so you can come back from holiday stronger than ever.

Illustrated by Louisa Cannell.
What Does Everyone Want Out Of This Trip?

Making sure that your expectations align is an essential part to creating an itinerary that everyone is happy with. Are you looking to veg out and recharge by the beach, or will you be joining walking tours to soak up a new culture?

Organize a group meet up ahead of planning a trip to hash out everyone's hopes and dreams for this vacation. This will inform the number of potential disagreements — on things like the choice of hotel to the wake up time — down the line. It's better to make compromises ahead of the trip, rather than have them spring up on the spot.
Illustrated by Louisa Cannell.
Is Everyone Happy With The Budget?

As the adage goes, "Friendship and money don't mix." And, when it comes to traveling together, having different budgets can really throw a wrench in the enjoyment of people participating in the trip. Coming to mutual agreement on how much money the group should spend on food, transportation, and entertainment may be a bit awkward at first, but can help eliminate arguments in the long run.

A good rule of thumb is for everyone to contribute to a set amount of cash to the "public fund" every day, which can then go into paying for expenses such as shared meals and gas. If anyone wants to order something extra, such as a cocktail, he or she will be responsible for paying up. This will dramatically cut down the amount of time spent splitting the bill and deciding what's fair.
Illustrated by Louisa Cannell.
Who Is Doing The Planning?

It's natural for certain people to assume the mantle of a planner, but it's important to not overwhelm one person with the task of coming up with an itinerary and logistics for the whole group. Everyone going on the trip should be responsible for listing all the things they want to accomplish on the vacation, and factor these goals as part of the plan — to a reasonable degree, of course.

One crucial thing to iron out? The time breakdown of sightseeing versus wandering around. One friend may be content with a doing quick walk through a street market, while others want to take the time to browse through every stall. It's a good idea to get everyone on the same page about the amount of time allotted for buying souvenirs — around 45 minutes per shopping destination is the sweet spot.
Illustrated by Louisa Cannell.
Will There Be Any Alone Time?

Traveling together doesn't mean that you have to be glued to one another 24/7. Taking some personal space can do wonders for the energy of the trip: It gives everyone the time to do their own thing, whether it's Skyping with a family member or checking something off their bucket list that others aren't interested in.

We'd recommend slotting in a "time out" on the last afternoon before your departure date. That way, everyone will already be somewhat familiar with the destination and the gang can still meet for dinner and a last hurrah. Another suggestion: If a friend has taken on the duties to be a translator or tour guide for everyone, make sure to buy him or her dinner to show your appreciation.
Illustrated by Louisa Cannell.
How Are Conflicts Resolved?

Personality clashes happen all the time in a friendship, but conflicts tend to become heightened while you're on the road. How you normally fight with this friend — and how these fights are handled — should factor into whether or not going on a trip together is a good idea. For instance, if your friend is prone to throwing hurtful statements and leaving the scene in a spur of rage, or if the way they deal with conflict is the silent treatment for days — it may not be the best idea to travel abroad together.

This also marks a good opportunity to access whether your life values are still compatible with each other: If you cherish a slower pace and cultural exchange, but the other person is looking to party it up — perhaps it's better to acknowledge these lifestyle preferences without judgment, and decide that traveling together might not be the best idea.