5 Questions to Ask Before You Travel With Someone

Do you want to go on a trip with me?


Before we decide to travel with someone, there are many factors we need to take into consideration beforehand. And as much as you want to take that epic best friends trip to this exotic location, are you SURE you really want to travel together? Or maybe you want to take an amazing trip with your significant other. Are you SURE they’re the right person to share this trip with? I’ve traveled with my family, my cousins, my aunts and uncles, friends, strangers, and my significant other. Here are five questions to ask before you decide to travel with someone, that could save you your trip!

1. Can you survive hating each other for a short period of time?

Traveling brings with it the excitement of uncertainty! And with that uncertainty comes the adventure, spontaneity, and the frustrations. Especially while traveling in a foreign country that doesn’t speak your native language, this can cause problems and mishaps. Can you survive hating your travel partner for a period of time? You’ll be spending every minute with them, going through the travel mishaps and excitement, but also going through the moments of annoyance and frustration. Will all of that affect your relationship afterwards? These are all important things to consider before planning who you want to travel with. If you both know you can survive being VERY annoyed with each other and hating each other for a short period of time, and still love each other afterwards, you’re on the right track!

Although I love my family and my friends, I know I wouldn’t be able to travel with them on certain trips. Good thing my family HAS to love me, no matter what, because I’m sure I annoy them just as much as they annoy me!

5 Questions to Ask Before You Travel With Someone
White Oak Canyon in Shenandoah Valley, VA
2. Do you have the same travel goals?

Everyone travels for a different reason. Some people travel to experience museums and all the tourist spots, others travel to meet people abroad, and some just travel because they think it’s what they need to do. Does your travel partner have the same travel goals as you do? This is one thing that I’ve learned is an important question to ask before planning a trip (or really anything you do)! You may have different travel goals than what your travel partner has, which may make your trip a bore, chore, or something that you end up not enjoying. One thing I always try to do is share my intentions BEFORE we leave. That way, whomever I’m traveling with, we can work through the itinerary and compromise where necessary.

You don’t want to travel with someone who has a completely different travel goal than you do! The trip might be more awkward, frustrating, and less enjoyable for both of you. If your heart is set on traveling with this person, or people, compromise!

5 Questions to Ask Before You Travel With Someone
Toledo, Spain
3. Do you have the same or similar budgets for the trip?

There is nothing MORE uncomfortable than traveling with someone who doesn’t have the same budget as you do. Whether you’re a big spender or a budget traveler, everyone spends differently. I consider myself to be in the middle ground of a budget traveler, but am willing to spend a bit extra for certain activities or food that will enhance my experience in a city or country. If you’re more of a lavish spender and traveling with a budget traveler, there are definitely constraints. And if you’re a budget traveler with a lavish spender, there tends to be a bit of exclusion.

While I travel, I enjoy being with people who have the same or similar budgets as I do. It makes me feel more comfortable knowing that they also understand my financial situation. I’ve traveled with extreme budget travelers before. Although I always try to be respectful of everyone’s financial situations, we both ended up feeling as though one person was holding the other back. I’ve also traveled with very lavish spenders and we weren’t able to compromise about activities because one of us didn’t want to do it, or the other couldn’t afford it.

4. Are you comfortable with traveling solo during any parts of the trip?

Kindof a silly question to ask if you plan on traveling with someone, right? But, this is actually pretty important! I love traveling with one or two other people because it allows me to share my thoughts, talk things over, and be able to try more things (food priorities?). But, I also love traveling solo because it pushes me out of my comfort zone, allows me to meet different people, and I’m on my own time and schedule. Just because you travel together doesn’t mean that you ALWAYS NEED TO BE TOGETHER.  Actually, that should be a life lesson (HAH!), but really.

When I traveled with various groups of people, there were plenty of times we ended up having “group think”. Which meant that because no one wanted to hurt anyways feelings or we were all trying to be likeable, we ended up doing the same thing because no one else spoke up. I am totally guilty of this. I’ve agreed to going places that I didn’t care for, done things that I didn’t have the money to do, or sat at home because everyone else wanted to rest, when I didn’t want to. This is something I still struggle with when I travel with people! I’m learning that it is FINE to go off by yourself if you want to.

5 Questions to Ask Before You Travel With Someone
Toledo, Spain
5. Can you both hold your liquor?

To be honest, I probably should have put this question as number one! Can you both hold your liquor? Unless you both don’t drink, experiencing the party/bar scene in a new place is half the fun of being in a different place. But, what isn’t fun is traveling with someone who cannot hold their liquor. I’m all about having a great time and enjoying a few drinks! But, while I am on a trip, it’s hard for me to go “PARTY MODE” because I never want to be hungover the next day (unless we really have nothing else to do).

Ask yourself if this person can hold their liquor, because it isn’t fun to be taking care of someone while you’re in a different area and expected to be exploring the next day. It also isn’t fun to be traveling while hungover, it just makes everyone slow.

So, do you want to go on a trip with me?

While these are a few questions to ask before you plan to travel with someone, I trust y’all’s judgement. Like I mentioned before, I’ve traveled with my family, my extended family, with friends, with strangers, my significant other, with my dog, and have been a third wheel on various trips. Each destination was different, but the one thing I learned was that no matter how AMAZING a place is, having the right people to share it with makes an enormous difference. Who is your favorite person to travel with? Why does it work? Let me know in the comments below! 

I will leave y’all with some pretty darn good advice from Bill Murray (even if you don’t plan on getting married with this person!):

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There are 5 important questions to ask before you travel with someone. And no, "Do you want to plan a trip with me?" isn't one of them! -- The Quirky Pineapple
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16 thoughts on “5 Questions to Ask Before You Travel With Someone”

  1. That happened to me, too! I think most people don’t realize that traveling with other people is actually an art form… and it can seriously make or break a trip! I’ve had a few moments after a group trip and thought to myself, did I really travel there? Or… did I just go there and take cute pictures haha! That’s great that you like traveling with your dad, traveling with my parents is also fun, but my mom likes to shop and my dad likes to go go go! My favorite travel partner is probably my partner, and we really balance each other out (:

  2. Omg haha I wrote a post on traveling with friends last year that talks about a lot of the same things – haha great minds think alike! Budget is huge, as well as travel goals and doing stuff alone. I’ve definitely done things I wasn’t super interested in because I with friends that wanted to and wouldn’t relent…now I’m like..nope, gonna do my own thing! I’m super super careful about who I travel with now, having had quite a few mishaps. I actually really like traveling with my dad because he’s super fun and always down for whatever – he likes when I plan what I want to do and just go for it! Also love traveling with my partner too of course though sometimes our travel paces are a bit different (I could go go go all day and he likes to take things a little more slowly)!

  3. That’s amazing! I am still looking for that one girl friend to travel with, where we just mesh together and really get each other travel wise. It’s proving to be a bit more difficult than I thought! Or, I’m just really picky and high maintenance… lol But I have also traveled with friends and it ended up being something where I thought it would have been more fun if I had traveled by myself to this destination.

  4. This is so true!!! I luckily travelled with one of my best friends for months and we just worked perfectly! We had the exact same budget ideas and everything, but I have travelled friends where it has been a nightmare and I swear I never will again!

  5. Oh my gosh, that’s a long trip! I couldn’t imagine planning it with someone and then learning that your travel styles don’t mesh. I hope the trip ended up going well, anyways! I also have a list of people I know I wouldn’t be able to travel with… and I’m sure I’m on other peoples’ lists, too! lol

  6. Hahaha, I wish the same, too. I have definitely learned my lesson about traveling with the wrong people!

  7. Oh gosh, traveling with someone with a different budget is so complicated. And I feel like sometimes it can really ruin friendships. Also, that’s another great question to add! I’m always really open to trying new types of food and unusual dishes from different countries, but I’ve traveled with people before who were SO PICKY that I would just get upset! Street food is also my jam!! Would love to meet up one day and roam around eating street food together until our tummies hurt hahhaa

  8. Lol thanks, Ro! (: That last question is such a deal breaker! When I was younger I never would have thought of something like that, nor would I have thought about it until recently! It’s such a deal breaker, and definitely something I always keep in mind now… after previous experiences hahaha

  9. Oh, definitely! Traveling with a couple is always a learning experience! There are days where my boyfriend and I really get each other, and then there are days where we just can’t seem to see eye to eye on things! Compromise is so important!

  10. Thanks, Ella! (: I don’t think I started asking these questions until very recently! When I first started traveling more and traveling internationally, I just thought it’d be a fun trip to go with my friends or with my family, whoever wanted to or could take the time off to do so! Eventually, I learned that there are certain trips that I can only travel with certain people haha and not everyone and I get along or agree on things when it comes to travel.

  11. This is sooo true! I once went on an epic (half way) around the trip with someone who turned out to have completely different ideas about the cultures and the way the travel would be. I was baffled. Needless to say, we didn’t travel together as long as planned to. Hopefully people will learn from your tips and my mistakes!

  12. Honestly, I do wish I had considered all of this before travelling with some people. Live and learn, of course. I don’t imagine I’ll be making the mistake of not asking these questions about possible travel partners in the future.

  13. #3 is so right! There really is nothing worse and plenty of friends have told me horror stories about traveling with someone with a different budget. I would add one more: similar food preferences! I’m not sure I could travel with someone who isn’t willing to try new types of food. Street food is my jam!

  14. haha. love the intro! “Wrong” lol. that last question is sooooo important 🙂 wish i had asked these questions before a couple of my previous trips!

  15. I love the questions that you suggest we ask, it will help us so much when we’re considering travelling with someone. I’ve actually only done solo trips so I have no experience with how to travel with someone else. These questions will definitely help me be more prepared when I finally choose someone to travel with. Thanks for sharing! 🙂

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