Traveling with friends is one of the most fun and rewarding experiences in life. Finding adventures, creating stories you will tell for years, and deepening bonds with people who are important to you. It’s also one of the most trying experiences you can go through, and quickly shows you the true colors of your friends as well as yourself.

I have found out there ain’t no surer way to find out whether you like people or hate them than to travel with them.

– Mark Twain

Spending days or weeks with someone in intense new situations where neither of you are in control can be exciting, and it can be harrowing. Here are a few tips to make sure things go well.

Come to terms with the kind of planner you are

fullscheduleSome people are heavy planners, researching and preparing spreadsheets scheduling each day down to the minute. If the schedule starts slipping, they get tense and snippy, doing all they can to keep control of the day. Other people just show up and let the world take them where it wants. When someone tries to constrain things to certain times, they get agitated and might wander off on their own, stressing out other people.

Personally, I like to research a place, build up a list of awesome things to do, and organize it by location. I might schedule a few things, but otherwise I just go to the next awesome thing I want to see, then find things nearby.

You need to find your own planning personality, though, and accept it. Then you need to figure out how your travel buddies plan and figure it out accordingly. If you both plan heavily, schedule some marathon planning sessions together beforehand so you are working toward the same goals. If you like to just show up, figure out a home base to meet up with people when you want to be social. If someone is a planner and someone else shows up, that’s when it gets a little tricky.

Talk it through beforehand. Have some days to be scheduled, and some to go off on your own. Most importantly, recognize that plans are going to change, and be ready to be flexible when everything goes wrong.

When everything goes wrong, that’s when the best things happen

Be flexible. When your boat ride gets rained out, pull out some cards and make some new friends. When you make a long trek somewhere only to find out it’s closed for a holiday you’ve never heard of, explore the nearby area or discover new food in a close-by cafe. Always be open to a different adventure than the one you had planned, because those are the best adventures of all.

The trips where everything has gone smoothly were enjoyable, but some of the least memorable. The trips where nothing has gone right are the ones I still talk about to this day. Sharing stories about how you discovered an amazing view of the city because you decided to hike behind the temple that was closed for construction, or the new friends you made because everyone was stranded somewhere together. These are the best parts of travel, and you won’t find them in any guidebook.

Have what you need to keep things social

Playing card gamesWhen you are traveling with friends, there are long periods of sitting somewhere quietly. Waiting for a bus, sitting on a train, or just collapsing in your room after a long day of travel. It happens all the time, and it’s easy for everyone to just hole up by themselves. What’s the point of traveling together if all of your social time is dictated by a schedule of when you are out and about? Carry a handful of things that keep the conversation flowing, even when everyone is exhausted.

First, a simple deck of playing cards. Pick one up beforehand on Amazon or find a novelty souvenir deck where you are going. Everyone can share their favorite games, and you will quickly find a group favorite that everyone keeps wanting to play.

Second, Monopoly Deal. I’ve recommended this one before, but it’s worked for me across so many countries and cultures that I’ve given away at least a dozen decks to new friends as a souvenir to remember the time by. It’s easy to pick up, packs small, and games last 15 minutes with lots of talking and negotiating. Incredibly fun.

Finally, something that most people don’t consider. Headphone splitters. Get the kind with volume control, so you can accommodate the differences in everyone’s headphones.

 When you really have to be quiet for a while, like on a trans-atlantic flight, being able to watch the same thing and talk about it later is great for keeping the adventure rolling. All it takes is one of these bad boys, and soon you are both laughing at the same jokes and caught up in the same storylines. Suddenly each downtime isn’t a slog through boredom, it’s a race to pull out the next episode and start laughing again.

Plan well. Embrace when things go wrong. Bring the social. This is the adventure of a lifetime, so make sure you enjoy it.