Ryan WingenrothComment

Who Do You Want To Travel With?

Ryan WingenrothComment
Who Do You Want To Travel With?

You’ve been planning this for a long time. Reciting the speech over and over again in the mirror so you don’t fumble through the words when the moment comes. The nerves bubble up every time those final words escape your lips. A final and committing request for partnership. Some take this request lightly. Too many. “What could go wrong? We get along great!” But this isn’t asking someone to lunch, or a casual invite for beer after work. This is a serious commitment, and you know it. The day finally comes, you see your longtime friend and hopeful partner approaching you with the same smile you are so accustomed to seeing. You don’t wait for a greeting, you drop to one knee and look straight into their eyes. You practiced this so many times, but the words seem lost. Your mouth goes dry and your tongue seems to swell as those all too familiar nerves numb your fingers and lips. You find the words and power past the stresses, “Will you…..travel with me?”

Huh? What are you talking about?


Yes! Who you travel with should be taken with much more significance than you think. Ok. Perhaps I am being facetious with comparing it to marriage, but it is not as crazy as you might think. Oh, it’s a vacation, its an adventure, who wouldn’t have fun? I have known my buddy for years, we get along splendidly, why wouldn’t we travel well together? All legitimate questions but think about it. Sure, the person that you would drop to a knee and ask for their hand in marriage should check a hell of a lot of boxes. But you may find that a spouse, a roommate and a travel partner have a lot of similar boxes to check. Anyone who has lived with roommates should be able to recognize the difference between someone that you enjoy hanging out with and someone you can live with. Or, someone you could travel with.

I have lots of friends. They are different shapes and sizes, they have varying temperaments and interests, their fitness levels are all over the map, some are morning people, and some are night owls. You get where I am going with this? I love my friends and how unique they all are. I have also learned that there are only a handful I could actually live with. I don’t like a roommate who is messy, who bitches and complains, who never does the dishes, who parties late every night, or any other number of things that I recognize as important factors in a roommate. Why would your requirements for a travel partner not be as strict?


You will undoubtedly spend more time with your travel buddy than you ever will with almost anyone else. When you travel with someone you will wake up with them, you will commute on long and often uncomfortable planes trains and automobiles together, you will walk with day and night with this person, you will struggle with them, and you will go to bed with this person. They will become an extension of you. People take more time picking out a bloody travel backpack than a travel partner. You can leave the backpack in the hostel when it becomes to burdensome, you can’t leave your travel partner. If you bought new travel shoes but find that they give you blisters when the terrain gets rough, you can toss them and get new ones. You can’t rid yourself of your travel partner when they constantly complain about the fact that you have been walking too long, grumble that you got off at the wrong train station, or whine about you wanting to get up early. Your travel partner can be a constant boost of energy and a source of support through the struggles of traveling. Or they can be a wretched boil on your ass. They can fight you at every turn and barrier. And it will be your fault. Your fault for not being as thorough with picking a travel partner as you were with your new water bottle, your Air BnB, your roommate, or your spouse!

I have done many trips with many people, and the difference between traveling with people of like mind and attitude vs traveling with those who are not, is remarkable. I have learned that there are maybe three people in this world who I could travel with. But let me be clear, I am not talking about taking a drive to a nearby city and staying a night or two, anyone should be able to have the capacity to accommodate your friend’s personality differences for that length of time. Unless you are a sociopath. I am talking about a multiweek trip, one that requires lots of commuting and where you will experience plenty of challenges and stresses. There is a HUGE difference. Having a likeminded travel partner can help to make these challenges part of the fun and make them an opportunity to discover and grow.


I have dozens of friends who I have known for decades, but I would only like to do a major trip with maybe three of them. Now, I love these people completely, and we are wonderful friends. But I don’t want to live with them, I don’t want to marry them, and I certainly don’t want to travel with them. This may all seem a tad harsh, but those who have traveled with the wrong people know what I am saying. I am a very positive and easy-going person, so I will have fun regardless of my companionship. But It can certainly make it more difficult. Now, these “wrong people” aren’t bad travelers, they are just bad for me. And that is the point of this. Figure out who you are, figure out what qualities you would want in a roommate or spouse, and make those the same things you would look for in a travel partner. Again, this may seem insane to compare marriage to a roommate and then to a travel partner. And it is not quite the same, of course, but I’m trying to stress how much time you are going to be spending with this person or people. I have roommates, I see them for perhaps an hour or two a day. At the most. That is 784 hours per year. Now, let’s say you are going on a three-week trip with someone, odds are you will see them from the moment you wake up till the moment you go to sleep. Every day. Let’s say you sleep 7 hours a day, that would give you nearly 357 hours spent together. That is equivalent to nearly six months of accumulated time spent with one of my roommates crammed into three weeks. That is a lot of time.

 I like to wake up early and fill almost every hour of every day with activities and fun, sometimes to the point of exhaustion. I need to work on slowing that down. I like to go off trail, I like to get Lost At Will, and I make a hell of a lot of careless travel gaffs that are caused by my flippant attitude. These can certainly be as frustrating to other people as their behavior is to me. So, I know what I need in a travel partner. I need someone who is patient, outgoing, has seemingly limitless energy, lets me lead but will also occasionally pull on my reigns, and is as positive and optimistic as is humanly possible. These are what I need, and though my requirements may seem unreasonable, they are honest. Be honest with yourself! Remember, 357 hours!


I am lucky, Jayme is the absolute perfect match for me. She always finds a way to laugh at the stupid mistakes I make, the ones that add chunks of times onto commutes because of my poor sense of direction. She is so optimistic it makes me look like a despicable pessimist. And I’ve always been the hopeless optimist! My father always said that on my headstone it will read, “It’ll be fine.” My favorite line in times of stress, confusion, or danger. “It’ll be fine.” Well, if those will be my final words before I plunge into the grave, they will be hard to hear over Jayme’s bellowing, “DON’T WORRY, IT WILL BE OK!!” as she narrowly beats me into the great beyond. The endless positivity, the willingness to let me lead until she sees I am leading us into quicksand, and her insatiable desire for a hint of danger and mystery. She is my perfect travel partner, can you think of yours?

In closing, I urge you to think hard about who it is you ask to join you on your next trip. And there better be a next trip… I hope that you are thinking about some sort of destination and then figuring who you want to join you. Be picky. Nobody would blame you for being picky in choosing a spouse or a roommate, so don’t let someone begrudge you for being picky with your travel partner. Now, unlike the long courtship that goes into choosing a spouse, choosing a travel partner should only take a few minutes of honest reflection. So, choose wisely, it will make the most remarkable difference in your trip. You want to pick someone who will become a force multiplier in your trip. Choose wisely my friends. It matters.