11 Super Important Questions To Ask Your Friend Before Traveling Together

Flickr / Jason Luk
Flickr / Jason Luk

Traveling with a friend means adventures, cocktails, and inside jokes that will have you in fits of laughter well after your return. We recently posted an article about how overseas travel will make couples stronger, and the same can certainly be true for friendships. Many times though, people go into a trip without communicating their expectations, which can lead to arguments, disappointments, and may even take a toll on your friendship. 

You don’t need to agree on everything — or anything — for that matter. Traveling with someone very different than yourself can actually be a great experience for both of you. But going into it with a clear idea of what your expectations are will ensure that you both get the most out of your travels and remain friends after your return flight lands at home.

Whether you’re traveling with your BFF, whom you’ve known since the time you could walk, or a coworker you’ve never seen outside of the office, there are some things you’ll want to discuss before heading through the airport security line.

1. Are you a planner or a free spirit?

For planners, there is nothing more infuriating than someone who just wants to go with the flow. And for spontaneous types, itineraries are the ultimate kill-joy. Find out where both of you stand on this issue. And be specific. For some people, an itinerary means just having a list of towns you plan to visit, and an idea of how long you’ll stay in each. For others, itineraries mean an hour-by-hour plan of what you’ll be doing, where you’ll be eating, and when you’ll take bathroom breaks.

There truly is no right or wrong way to plan (or not plan) a trip, and both types of travel can be equally rewarding. If you truly can’t come to an agreement, divide your trip in half. Make a plan for the first half, and allow yourselves some freedom for the remainder. You’ll both learn something — even if it is how much you hate traveling with (or without) a plan.

2. Do you want to go-go-go, or take it slow?

Speed of travel is one of the most important things to talk about since it will determine just about every aspect of your trip. 

Some people prefer to pack in as much as they can, and they don’t mind hopping around from hotel to hotel. Others (myself included), prefer to spend at least a few nights in each place and really get to know the locale, even if that means they’ll see less places in the end. Discuss both of your preferences, and find a happy medium. 

3. What’s your budget?

It’s time to talk about money. You’ve gotta be blunt — there’s no way around it. If you’re traveling with a companion, you’ll want to have a ballpark figure of what they’re hoping to spend. You don’t want to go in expecting upscale restaurants and accommodations only to find your friend has a dorm room budget. Get the awkwardness out of the way, and talk numbers before planning anything else. Hashing it out ahead of time will prevent some potentially uncomfortable situations on the road.

4. Luxury or Low-maintenance?

Now that you have an idea of a rough budget, talk about the type of travel you hope to be doing. Do you enjoy roughing it, or do you prefer the comforts of home while you’re on the road (even if it costs more)? 

Dig deeper: How long can you go without a shower? Is an overnight bus a deal-breaker? What are your thoughts on hostels? What about dorm rooms? What comfort are you not okay going without? 

All of these questions will help you determine what type of accommodation, transportation, and activities will make both of you happy.

5. What’s going to be your splurge?

An hour-long massage on the beach? Whitewater rafting? A really nice meal? Discuss a couple things you’d be willing to spend more money on. This way you have an idea of your priorities. Plus, you can help each other stay on budget so you’ll have enough money for that special souvenir or outing. 

And perhaps you don’t have any room to splurge at all. Be honest so your partner has an idea of what to expect and can help you stay accountable to your spending plan.

6. To party or not to party?

First of all, define your idea of a party. Maybe a wild night for you is kicking back with a local beer and playing a feisty game of Jenga. Your friend, however, drinks only top shelf liquor and their idea of a good time is dancing ’til sunrise at the trendiest club in town. Do a little of each, or be okay going your separate ways come nightfall. 

Also, decide how often you plan on partying during your travels. I’m not suggesting you make an itinerary that details the nights you’ll go out. But do discuss your expectations. You may want to do a lot of sightseeing, but perhaps your friend is hoping to plan the days around your nocturnal escapades. Figure out your party priorities together. 

7. Set an alarm, or wake up whenever?

Do you want to get a start on the day before the masses of tourists are out and about, or do you prefer to take your mornings slowly while on vacation? Perhaps one of you wakes with the sun and the other hits snooze 27 times before actually getting out of bed. So what do you do? I’ve traveled with people who have very different sleep schedules than myself, and it works fine as long as we are respectful to the other’s habits. If you’re okay with your friend turning in for the night early, they’ll respect your “no talking before 9 a.m. policy”. You may also need to compromise and start some days a little earlier than you may prefer, and vice versa. 

8. Street Food: Delicious or Gross?

Are you a picky eater, or would you consider yourself adventuresome in the culinary arena? Food is a huge part of traveling, and you won’t want to wait until you’ve made it to your destination to find out that your travel companion doesn’t eat much other than chicken fingers and mac ‘n cheese.

Furthermore, street food is a huge part of culture in many countries. And it’s a great way to get a taste of the local flavors for a fraction of the price you’d pay at a sit down restaurant. We all have friends who wouldn’t dare eat something cooked from a stand on the street. Maybe that’s you. Lay it all out on the table (see what I did there?) and share any food phobias you may have, or things you simply refuse to eat.

More questions to consider: Do you have a daily budget for food? Do you have any dietary restrictions? Is there anything you definitely want to try while traveling? Is there anything you absolutely won’t eat? And back to the original question: How do you feel about street food?

9. What are you looking forward to most?

Say you’re planning to visit Italy, and you’re absolutely dying to browse the Uffizi. Your friend is not exactly the artsy type, and never thought to put Florence on the itinerary. To say you’ll be disappointed is an understatement. Lay out the things you absolutely must do ahead of time so that neither of you is let down.

If you are looking forward to different things, that’s fine! Maybe your friend would rather go shopping than step foot in a museum. Split up for the day. There’s no rule that says you need to spend every waking minute together. But deciding this ahead of time will make it less awkward in the moment.

10. Hitchhiking: Stupid or Adventurous?

People have different ideas of what constitutes adventure. What sounds thrilling to you, may make your friend incredibly uncomfortable. It may be hard to compromise here. I mean, when it comes to bungee jumping, you can’t exactly go just halfway. So instead of trying to find a middle ground, make an effort to respect each other. Your friend doesn’t want to bike on the most dangerous road in the world? Don’t pressure them. And if you are looking forward to skydiving, your partner should refrain from telling you all the reasons it freaks them out. Hopefully you’ll find some things you can do together that you both consider adventurous.

11. Let’s talk about stress, baby!

Traveling isn’t all relaxing in hammocks and sipping piña colada on the beach. I hate to shatter this illusion, but things won’t always go according to your plan. The airline might misplace your luggage or your hotel might lose the reservation. It’s helpful to know how your partner will handle stress if an unexpected situation arises. 

Discuss what in particular stresses you out. Perhaps the feeling of not being in control makes you want to want to scream. Or maybe going a long period of time without food will transform you to Mr. Jekel (I’m not even going to pretend that last one isn’t about myself).

Delve in a bit further and talk about how your partner should approach you when you’re stressed. Some people need space, while others need to talk it out right away. Knowing what your friend responds well to will make the situation go so much more smoothly. And before you know it, you’ll be sipping fruity drinks on the beach. Hey, I didn’t say piña coladas and hammocks aren’t part of travel, after all. Thought Catalog Logo Mark

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Katie Diederichs

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