How to Have a Smooth Journey with Friends: Tips for a Disaster-Free Trip

A few years ago, one night over dinner with some friends with whom I shared a love of gourmet food, sushi, great cocktails, politics, and movies, we realized that in all the years we’d known each other, we had never taken a trip together.

As we all had lots of points and miles saved, we thought about how fun it would be to go somewhere spontaneously.

“Let’s do it,” we all declared. So we found award tickets to Hong Kong for the following week.

Halfway around the world, we arrived at our hotel late in the evening. After a late dinner, we went back to the hotel, where I decided to go to sleep. As fun as Hong Kong is at night (and it is very wild), I wanted to try to adjust to the local time zone, so I could make the most of the rest of our trip.

My friends had other ideas: they were going to party. So I said good night and off they went.

When I woke up, it was still dark out. I looked at the time. It was 5:30am. I found two of my friends asleep; the third was apparently still out partying.

Letting them rest, I got ready and headed out to enjoy the city before the commuters rose and it became a maelstrom of noise, chaos, and crowds. Hong Kong is one of my favorite cities, and I love its peaceful calm in the morning. It’s all grandmothers and grandfathers out for walks, doing tai chi in parks, and eating dim sum.

With so much to do (and eat), I didn’t want to waste any time. After an early breakfast of dim sum, I wandered around, grabbed some tea, read a book, and took photos of empty streets.

It was midday when I finally heard from my friends. We met for lunch at a noodle shop and plotted our day.

Before we booked our trip, I had asked them what they wanted to do. Knowing them, I knew it would involve fancy dinners (Hong Kong has some really fine dining), but I emphasized that as a backpacker at heart, what I really love are hole-in-the-wall restaurants, cheap activities, wandering around, and just enjoying the day-to-day life of a place.

“No problem,” they said. They were travelers too, and they also wanted to get below the surface. The idea of dim sum, markets, and fun local bars appealed to them as much as it did to me.

But that was not what happened.

My friends stayed out late partying every night, slept in late, only wanted to eat at expensive restaurants, and didn’t want to do any sightseeing.

As the days ticked by, we were like ships in the night. Outside a few dinners, I didn’t see too much of them. But, being used to traveling alone, that was fine with me. I can make my own fun. But it was disappointing not to have time with my friends. It defeated the purpose of the trip.

On the way back to the airport, they talked about doing it all again someday. But not me. I thought to myself, “We’re never doing this again.”

The trip taught me that, while people might like a certain travel style in theory, the reality is often very different. In fact, over the years, I’ve traveled with many friends who have completely different styles than I do.

As Mark Twain said, “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.” I couldn’t agree more. It’s important to be cautious when traveling with anyone, even your closest friends. It’s a very personal experience, and you’re going to want to make sure their style matches yours.

After many successful — and not so successful — trips with friends (some of whom I count as my closest), I’ve come up a list of questions that I think are important to ask people (of course, you know your friends, but I’ve found this still helpful):

• What activities do you want to do?
• I like [activity]. I’ll probably see/do lots of this/these on our trip. Would you come with me?
• How do you feel about [activity]?
• Are you okay doing things alone, or do you want to do everything together?
• I don’t eat a lot of expensive food on the road. How do you feel about that?
• Are you okay with eating street food?
• I like to be out the door by 9am each morning. Do you? (Or: I’m a night person. Are you okay with a late start?)
• Do you plan to stay out late?

It’s fine if you all aren’t on the same page, so long as you are comfortable with spending time apart. If you have different travel styles but aren’t okay being an independent traveler (or vice versa), that’s going to cause a problem. I’ve had plenty of trips with friends where we only overlap on some stuff, but that was not a problem. No one cared when any of us went off to do our own stuff, and it gave us things to talk about when we came back together later.

The more trips I’ve taken with friends, the more I’ve gotten smarter about which I take trips with. But sometimes you just never know ahead of time. What people say and what they do can be two different things. They may say they want to travel the same way or do the same things — and then you get on the road and it’s the opposite.

But, ever since that big spontaneous trip with friends, I’ve learned that asking the right questions in advance can really reduce the likelihood that you’ll run into these kinds of conflicts.

Use my list — or come up with your own — but don’t go on a trip with a friend who isn’t at least 60% aligned with your style and interests!