Have you ever traveled with someone, only to have the trip be a complete bust? Not exactly the thing you want to have happen when you’re parting with your well-earned cash to give the experience a go, is it? Here are some things you can consider and do to help make the next trip as good as possible.

Choosing Someone to Travel With

First, choose someone you enjoy. While it seems like this should go without saying, in practice it’s easy to get caught up in travel plans with someone that, if you stop to think about it, you don’t really have a lot of fun with. Or perhaps the person requires a lot of effort, even though they’re fun. But if that friend drains your emotional reserves, you might want to choose someone else. Same goes for friends who you might have to bail out of jail for picking a bar-fight. Or for someone who’ll likely freak out at the sight of a gutter-rat or go mental when your cabana has a few geckos and no hot water.

Secondly, assess what you want from your trip so you know a good match when you find it. At first just jot down whatever comes to mind regarding what you’re looking for in your vacation. Most often, the first things to come to mind are also some of the things that matter most to you. Once you’ve done that, consider the other four elements we talked about yesterday (the four besides who to travel with, that is). Together this will give you a pretty good framework for discussing your trip with a potential co-goer.

Also, consider your priorities. What is most important to you? One way to think about this is to complete the following sentence: “If I go home and I didn’t _______, I would be disappointed.”

Last, consider where you are open to going. Is your list short? Own it! Or are you just looking for some exploring or R&R and don’t really care where the path takes you?

Traveling With Others

Sometimes you have the luxury of choosing an ideal traveling partner. More often, though, you kind of end up traveling with who you’re traveling with, whether that’s your family or just the person who had extra time and money on their hands.

In preparation for this article, I talked to a few friends who had recently traveled with others and asked what they would say about the experience. I heard some good stories (and some bad ones), but every success and failure boiled down to one thing: communication.

You’ve already thought about your aims, your availability (time), and your budget. So share these with your travel partner. And don’t forget to listen to the other person’s hopes and limitations as well as expressing your own.

In addition to those three things, talk about how much time you’d like to spend together and how much time you’d like to spend alone. I like to spend a good bit of time alone inside my head each day. It’s helpful if my traveling companions are sensitive to this. I’ve found that communicating it up front helps me get the time alone I need, and helps my friends not misinterpret my time away from them.

Also Worth a Mention

Being a good travel partner probably deserves a dedicated post. As many of us have had stinky co-journers, we certainly don’t want to be one of them. So be the travel partner you want to have. Particularly, make it your aim that your companion would get to do what is important to them. Hopefully they’ll do the same for you.

Traveling with others can be an incredibly rewarding experience. You’re not alone. You’re not as vulnerable. You’re building into a relationship. But above all of that, you have someone to process your experiences with, and have the benefit of seeing things through someone else’s eyes. Which can make your travel all the more rewarding.

What About You?

Have you had any wonderful or awful experiences traveling with other people? What did you learn? What advice would you give?

This week we’re talking about travel planning. Here are links to the whole series:

1. Introduction
2. 5 Things to Consider When Planning Your Next Vacation
3. How to Select Travel Companions and How To Enjoy the Ones You’ve Got
4. Travel Budgeting
5. Getting Away on the Cheap

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