Is there anything worse than realizing after you’ve booked a trip with someone, that you have very, very different ideas of what you’re trip should look like? I’ve heard horror stories of newlyweds realizing they hate traveling together while on their honeymoon, and of lifelong friendships ending because each person wanted something totally different out of a vacation they’d already sunk lots of money into. Before confirming your travels with another person for the first time, regardless of how well you think you know them, have an honest discussion with them to make sure you’re on the same page when it comes to where you’ll be staying, the types of restaurants you’d like to eat at, what you’ll be doing, and most importantly how much time you’ll be spending together, among other things. If you can’t have an honest chat with them about how your travels should look up front, you may need to choose another adventure partner.
What Does Traveling Mean to You?
Find out how they like to travel. Is a vacation a reason to sleep in late, watch a lot of TV in another country, wander around at a leisurely pace, and go wherever strikes your fancy, or is it an opportunity to exercise each day, wake up early to go siteseeing before it gets crowded, and pack as many new things into each day as possible? If you both want different things out of a trip, it likely won’t end well, unless you’re each okay traveling more or less alone, which leads me to my next discussion point.
Private Time vs. Time Together
Figure out how much time you want to spend together during your holiday. If you want to go solo all day and meet up at night, but your friend wants to stay together the entire time, try to compromise and plan out days you’ll be together, and days you’ll explore independently, and see how your friend reacts. If they seem excited and agreeable to compromising, then it should work out. If they seem disappointed or hesitant to go out alone, or bring up worries about being separated from you, it may not be a good fit to travel together, unless you’re willing to compromise for the sake of adventure.
It isn’t fair to bring someone on a trip if they think you’ll be spending the entire time together, and then you end up ditching them most of the time, just as it wouldn’t be fair if these roles were reversed. Travel with someone who has the same expectations with you, and be open to compromising. Traveling can be a fantastic way to get to know your friends and loved ones better, so relish in the opportunity to share in new experiences together.
While on this topic, see if they want to share a room with you (cheaper, but less privacy), or if they plan to get their own room the entire time (more expensive, more privacy). If one wants to share a room and the other doesn’t, this needs to be discussed before finalizing plans, as it can significantly alter the cost of traveling together in either direction. Sharing a room with a trusted friend may mean you can upgrade to a nicer hotel, bigger room, or a suite in a luxury hotel, which can make for a dream vacation, but it can also mean having to share a space when getting ready (i.e. only 1 bathroom, fewer electrical outlets, staggering showering times, etc.), you may be able to hear your friend snoring at night, or if they sleep with the TV on and you need it to be silent, issues could arise. Talking about these things will help set expectations, and boundaries to ensure smooth travels.
Scheduling & Itineraries
One of the most important things to ascertain before heading out with a friend on a trip is how they like to plan (or not plan) their travels. Find out what time they go to sleep and wake up during vacation. This is usually different than a person’s typical waking and sleeping schedule. If you want to wake up and start exploring before sunrise, and the other person wants to sleep in past noon every day and expects you to wait for them until they wake up, you’re probably going to have a bad time. If you’re a person who wants to plan out every moment of the trip and arrange timed tickets in advance, but your friend is so casual you can hardly peel them away from a street performer or cool mural when you’re late to something, your trip likely won’t end well.
Find out if they like to stick to a set schedule, or if they’d prefer to wing it. Ask how disappointed they’d be if they miss a thing or two on the itinerary if something comes up. How flexible are each of you when it comes to traveling? In general, people should travel with others who travel at the same speed they do. If you love scheduling every moment of your day out from the time you wake up until you go to sleep, but your friend wants to just lounge on the beach and read a book one day and wander where the wind takes them the next without any regard for a travel plan, you may want to find someone else to travel with.
Furthermore, figure out what level of activity each of you likes when traveling. If you’re someone like me who loves to try new things like SCUBA diving, snorkeling, and loves hiking, biking, walking, and siteseeing all day, every day, you likely wouldn’t enjoy being with someone who wants to lounge the entire time. If you’re able to strike a balance, where each of you has times to do what you each want, whether together or independently, that is ideal, but if not, it could be a deal breaker.
Other People & Partying
This sort of ties into the “Private Time vs. Together Time”, and the rest of the topics as well. Find out if they plan to link up with other people they meet along the way, if they intend to go over to another person’s place or meet up with other friends at some point. Set some ground rules on bringing back people or strangers back to your room, especially if they invite someone to stay the night that you don’t know. If you’re not comfortable sleeping three feet from a random stranger, or you would rather not group up with people you’ve only just met for half your trip, discuss this beforehand, set boundaries, and agree to stick to them so that no one’s feelings are hurt in the heat of the moment.
Does your friend plan to get messed up (substances/booze/etc.) or go out partying every night? If you’re not into that, I recommend traveling with someone who aligns with your beliefs, because this can cause a lot of issues and tension. One of my college friends was detained and briefly jailed abroad because her roommate that she’d been traveling with had brought drugs into another country during their spring break trip, which obviously not only scared both of them and got them into tons of trouble, but it completely ruined both their vacation and their friendship. My friend didn’t even know that her roommate was into that sort of thing, so it was a very rude awakening for her, and she was implicated by association, which was especially scary since they were abroad. Know who you are traveling with, and don’t put yourself into situations you aren’t comfortable or experienced with, to whatever degree possible.
Luxury vs. Economy
Determine what level of luxury (or lack thereof) your companion is comfortable with. If they want to stay in hostels and only eat street food when you’d prefer to spring for a room at the Ritz and dine at Michelin Star restaurants to experience the best of the best your new city has to offer, you may be better off traveling with someone else with a budget more like yours, unless you don’t mind covering for them.
Use Pinterest, Google, and my website to find places you’d like to eat and stay, map out your budget a bit before to get a vague idea of how much you want and are able to spend each day, and compare that to how much your friend is willing and able to spend daily. It may seem a bit gauche to compare finances like that, but when traveling with someone it will inevitably come up sooner or later, so get it out of the way before finalizing plans to ensure that you’re looking for the same experience. If your plans and financial expectations don’t align, look for ways to compromise.
Even if you’re not a very detailed planner, and particularly if you are, discussing these topics will help prevent any troubles before they come up, and will help keep your travels smooth, pleasant, and as enjoyable as possible. It will also help you decide whether or not to stake a vacation, friendship, or both on a new travel partner. Hopefully, you’ll find that you and your intended companion share the same expectations, and can move forward with planning your adventure worry-free!