Traveling with friends: how to avoid disaster

A few years ago, one evening at dinner with some friends who shared a passion for gourmet cuisine, sushi, fine cocktails, politics and films, we realized that in all the years we had known each other we had never taken a trip together.

Since we had accumulated a lot of points and miles, we thought how fun it would be to go somewhere unexpectedly.

“Let’s do it,” we all said. 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 headed back to the hotel, where I decided to go to sleep. As much fun as Hong Kong is at night (and it is very wild), I wanted to try to adjust to the local time zone so that we could make the most of the rest of our trip.

My friends had other ideas: they were going to party. So I said goodnight and they left.

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

Leaving them to rest, I got ready and went out to enjoy the city before the commuters got up and it became a whirlwind of noise, chaos and crowds. Hong Kong is one of my favorite cities and I love its peaceful calm in the morning. There are grandmas and grandpas walking, doing tai chi in the parks and eating dim sum.

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

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

Before booking the trip, I asked them what they wanted to do. Knowing them, I knew it would be fancy dinners (Hong Kong has some really fine restaurants), but I stressed that, as a backpacker at heart, what I really love are hidden eateries, cheap activities, wandering around, and just enjoying the daily life of a place.

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

But it didn’t go that way.

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

As the days went by, we were like ships in the night. Aside from a few dinners, I didn’t see many. But, being used to traveling alone, it was fine with me. I can have fun alone. 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 one day. But I didn’t. I thought to myself, “We’ll never do this again.”

Travel has taught me that while in theory people might like a certain style of travel, the reality is often very different. In fact, over the years, I have traveled with many friends who had completely different styles than I did.

As Mark Twain said, “I have found there is 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’ll want to make sure their style matches yours.

After many successful and less successful trips with friends (some of whom I consider my closest), I have compiled a list of questions that I think are important to ask people (obviously, you know your friends, but I found this list helpful anyway):

• What activities do you want to do?
• I like [activity]. I’ll probably see/do a lot of this/these on our trip. Do you want to come with me?
• How do you feel about it? [activity]?
• Are you comfortable doing things alone or do you prefer to do everything together?
• I don’t eat much expensive food when I travel. What do you think?
• Are you comfortable eating street food?
• I like to leave the house at 9 every morning. How about you? (Or: I’m a night person. Are you okay with a late start?)
• Are you planning on staying out late?

It’s okay if you’re not all on the same page, as long as you’re comfortable spending time apart. If you have different travel styles but aren’t comfortable being independent travelers (or vice versa), that’s going to be a problem. I’ve been on plenty of trips with friends where we only overlapped on a few things, but it wasn’t a problem. No one cared when one of us went off to do our own thing, and it gave us conversation starters when we got back together later.

The more I’ve traveled with friends, the smarter I’ve become about who I travel with. But sometimes you never know in advance. What people say and what they do can be two different things. They can say they want to travel the same way or do the same things, and then you go on a trip and it’s the opposite.

But from that big spontaneous trip with friends, I learned that asking the right questions up front can actually reduce the likelihood of running into these types of conflicts.

Use my list, or create your own, but don’t go on a trip with a friend who isn’t at least 60% in line with your style and interests!