Updated: July 17, 2023

Once upon a time, in a previous blog post, I quoted John Steinbeck:

“A journey is like marriage. The certain way to be wrong is to think you control it.”

For me, this is one of the most accurate descriptions of traveling. Traveling is a volatile activity. This statement becomes even more relevant when we decide to travel with a second person.

Traveling alone does offer great benefits but organizing a vacation with a friend or loved one can yield the rewards of shared memories that will last a lifetime and a resounding sense of teamwork.

Achieving this feeling with a second travel partner requires a lot of effort. A two-person adventure is one of the ultimate tests of the strength of the bond between those involved. In my opinion, one doesn’t truly know another person until they’ve each put on backpacks and stepped into the unknown together.

I’ve been fortunate enough to plan various two-person trips, the longest lasting four months, and have seen journeys go well and not so well. If you’re reading this now and want to embark on a future trip with a second person, then I have compiled a list of ten important rules to follow for people who are considering this sort of adventure.

This list does not guarantee a positive traveling experience, but I believe it will increase two people’s odds of coming back happy and more importantly together.

Here it is:

Know each person’s travel goals

This is perhaps the most time intensive step. If you can get on the same page with the other person then your trip will have a really good chance of being successful. What do you want to do on this trip? What does the other person want to do? Maybe one person just wants to party while the other wants to wake up early to visit museums. If you both know in advance what the other person hopes to accomplish then you can make an agreement to please both’s desires and necessities for the trip. Trips are most fun when both people either have very similar interests, or are flexible to let everyone do some of the things they want.

Respect the other person’s budget

We all have different financial limitations. Agreeing on a budget, or at least agreeing on which things to splurge on, will create a fluid system of planning. Knowing the spending habits of the person you’re with will also prepare you for what to expect while on the road. Being flexible and willing to meet someone in the middle will go a long way.

Establish a payment system

Unnecessary frustration can be avoided if both people are prompt in paying the other person back on random expenses. For example, if one person offers to put a dinner bill on their credit card then the other shouldn’t hesitate to either foot the next one or send a mobile payment via PayPal or Venmo. To keep finances equal then an expense calculating app such as Splitwise would be useful. The financial aspect of a trip can easily become a tangled mess if both parties aren’t keeping track of their split costs.

Decisions now involve “us”

When electing to take a vacation with a second person, all decisions must go through both individuals. Agreeing to share an experience away from home means that both travelers have formed a temporary bond similar to marriage. As both people are investing time and resources into the trip, then both are entitled to make decisions and be in the know of the other person’s ideas. Communication is paramount here and both people should be flexible. Everyone involved should be able to do at least some of what they really want.

Establish a clear sleep system

Not every traveling duo will have the same sleep cycle or habits. One person might enjoy sleeping in while the other is an early bird. Before traveling they should agree on a system for staying out or sleeping in. This will avoid any potential resentment or frustration because their time-clocks aren’t in sync. The early bird might be ok with going to a coffee shop to let the other person sleep or the night owl won’t mind checking out a bar alone once in a while.

Establish general boundaries

Knowing what your level of comfort is before traveling is important. Will you be willing to eat a fried scorpion or go bungee-jumping? Will your travel companion have similar restrictions? Being aware of how far each person is prepared to go will be good for avoiding any potential miscommunication or conflict of interest. Having similar boundaries will allow both parties to travel with greater ease.

Take turns with tasks

It’s a good idea to give each person a responsibility during the trip. To avoid future resentment, it’s advisable to split tasks at different stages of the journey. For example, if one person did all of the reservations or research, then they might feel frustration towards their travel mate. Taking turns to book flights, bus tickets, or accommodation will help maintain harmony between both people.

Be empathetic

As I said before, we truly don’t know a person until we travel with them. It’s important to remain empathetic and free of judgement. This might be the first time you go on the road with that special person. Their morning ritual, funny little travel good luck charm, desire to call their mom, or random habit of cracking their knuckles before breakfast might not be something you’re used to. We are all weird people in our own special way and if we’ve said yes to traveling with someone then we’ve said yes to their uniqueness. On the flip side, we also must be aware of the fact that maybe our habits while alone aren’t proper for a two-person trip so we must be respectful of the other person. Remember: This trip is to have fun and not focus on the things you find off about the person you’re with.

Be present

This rule can be true for solo travel as well. If we agree to travel with someone, then it’s ideal to focus on the experience with that person rather than other people we meet or our devices. An optimal travel experience should involve less screen time and more focus on the surroundings. We miss opportunities when pegged to our smart phones and chances for meaningful conversations. Two people will have a truly memorable trip if they can remember to adhere to this system.

When one person uses the toilet, everyone uses the toilet

The last and most crucial rule for traveling with someone else is to reduce the number of bathroom breaks as much as possible. Let’s say you both find yourselves in a remote village or hidden beach and suddenly discover a chance restroom. In many areas of the world restrooms are a dime a dozen so it’s best practice to take advantage of this rare opportunity. If your partner has an urge to go but you don’t, you should still do it. Bathroom breaks equate to slowing down and stopping for a moment. Sometimes, if you’re in a busy place, there will be a line so why not have everyone have a go at it? The goal while traveling is to wander and enjoy rather than wait in line for a toilet so it’s paradigm to be efficient with these respites.

I hope you’ve enjoyed this article and can use these rules in your future wanderings. Right now the state of the world doesn’t allow us to fully enjoy traveling but we are getting closer to that moment.

Hang tight, stay safe, and take care of yourself.

Also, what are your rules for traveling? Do you agree with me in this article? I’d love your feedback!