How to travel with friends (and stay friends): Advice from an NYC etiquette expert

The road trip upstate with your best bud, camping with your crew from college or visiting a new country with a romantic interest. It can all be great – until there’s conflict.

Maybe you want to get up early, but your friends want to party until dawn. You want to hit up a museum, but your friend wants to people-watch at a cafe. You try to compromise, but no one ends up with what they really want.

“Just because we enjoy hanging out with them in the city, it doesn’t mean they’re actually a great fit for us for longer periods of time,” said Nick Leighton, an etiquette expert based in Manhattan.

“It doesn’t mean that they’re not good people. It just means our styles are a little different,” Leighton said. “We want to try to figure that out before we end up in Tokyo together.”

Travel gone awry can be so contentious that by the time you return home, you don’t even want to talk to the person, except you’re both in the same softball league and group chats. How can you travel with friends and still be friends after?

To navigate this question, WNYC’s Kousha Navidar caught up with Leighton, who is also co-host and producer of the podcast, “Were You Raised By Wolves?”

An edited version of their conversion is below.

Navidar: Why do you think it is so common to have this kind of friction around travel?

Leighton: I think a lot of people are unrealistic about how they travel. Like, how do they handle jet lag? How do they handle low blood sugar? How do they handle being stressed out about missing a train? Then how do you deal with the other people on your trip as we’re all experiencing these problems?

We often talk about, “Oh, you should set a budget,” but that’s actually not enough. It’s about how do you set a budget for the things you care about. I could afford an expensive 10-course degustation menu on vacation, but I don’t want to spend the money on that. It’s not enough to talk about budgets. We have to talk about priorities.

What do you think about alone time?

That is key, and we don’t need to apologize for it. I think everybody also wants it, too. You can just say, “Hey, when I travel, I like to have my days free, but then I like to reconnect in the evenings. Is that how you also like to travel?” Chances are, they’ll say yes.

What if alone time isn’t possible for whatever reason? How do you get through those difficult moments?

I actually took a trip with a good friend, where it was required that everybody was all together the entire time. Actually, this was to North Korea, so it was very supervised. And you just go with it. It’s not going to be the beach side, all inclusive, bring-me-another-cocktail kind of trip. That’s just a different flavor of vacation. It’ll be over at some point.

What kinds of questions should you be asking yourself before taking a trip with a friend?

Know thyself. Oh, now, we’re getting philosophical.

Absolutely.

I think we all have a good sense of, like, “Are we morning people? Are we evening people?” Also, what’s the goal of this trip? Why are we going on this vacation at all? Is it for relaxation? Is it a “You-Pray-Love” thing? Is it to see the museums? It’s okay to be honest with yourself or the people around you about what you need to have a nice time. If somebody has a very different idea, then the question is: “Do I compromise or can I come to some common ground on this?” Or maybe we shouldn’t have this trip together.

Any tips for how to tactfully say no?

In the etiquette world, we would say have a very polite yet direct conversation. Just rip off the Band-aid. We want to use a tone that’s nonjudgmental, value-neutral, and it’s just, “Hey, actually, I think that maybe we’re not on the same page about this trip and I think maybe it’s best that we actually don’t move.”

What kinds of conversations should you be having around money when planning a trip?

I think that’s the biggest issue. At the end of the day, if you were going to stop talking to somebody over a trip, money was probably related. We want to make sure we’re on the same page in terms of budgets and priorities. Are we prepared to have that expensive meal out? Even if we can afford it, are we willing to spend the money? We definitely want to have that conversation.

Then it’s about keeping track. Nobody wants to feel taken advantage of. No one wants to feel like they’re not carrying their own weight financially. There does need to be some plan for how are we going to be splitting and keeping track of all of these shared expenses?

One app I like to use is Splitwise. It’s very easy: You just put in what everybody owes. It actually can handle multiple currencies. Then you could just see, “Oh, this is the running tally.” I think that’s a good way to do it because everybody should just pay their own way.

What if your friend makes a lot more or a lot less money than you do?

If they ordered a pasta dish that costs whatever it costs, just because they make more money doesn’t mean they should pay for your meal, right?

However much somebody’s net worth is, does it really matter in terms of how much they’re spending on this trip? If they have very expensive taste and they’re like, “Oh, we must go for a spa day –

Yes, that’s more of what I’m talking about there.

– “And you must come with me.” Then you say: “Well, unfortunately, that’s not in my budget for this trip, but I’ll see you for dinner.”

When conflict does come up during a trip, what are the best steps to take?

We just want to be adults. We have to be polite but direct with people, like, “Oh, this is not working for me, and here’s what I need to have happen. Is that possible?”

It’s kind of the vibe. You have to read the room and see how having a direct conversation would be received. If it’s not going to be received well, then yes, you just tough it out and you learn your lesson. Never travel with those people again.

It’s fine to have one bad vacation with somebody. It’s totally your fault if it happens twice.

What about when you get home and you’re feeling hurt? What do you do?

Don’t let anybody owe anybody money. Settle the debts immediately because it’s so rude to make people chase after money. Make sure all the accounting is clean.

If something happened on that trip and everybody’s a little hurt about it, let the dust settle. Give it a beat. I think if these are important relationships that you want to maintain, then yes, have some conversation about it with the person about what happened, how it made you feel, and what might be done differently in the future.

Sometimes, though, you’re like, “I’m good with that relationship. That was enough for me. These are now acquaintances, and I’ll be polite when I see them, but I’m not going to make an effort to see them.” Then yes, you could just leave it there.

Has that ever happened to you?

Oh, I definitely move a lot of people into the acquaintance category all the time. I actually use a metaphor called “my theater metaphor,” where we have my close friends on stage, we have people in the front row, people back in the orchestra, up in the balcony, and I’m reseating people in my life all the time. You do something, and you were a balcony person, you might get moved to the lobby. I definitely move people in my personal metaphorical theater all the time.

If you’re on a trip with friends, of course, it seems like a gamble. Do you think it’s worth it?

Oh, sure, yes. Like the friend I went to North Korea with – it deepens a friendship being somewhere like that. These trips, they’re memory-building and they’re fun, and who wouldn’t want to share something great with the people that you’re friends with? Like, who wouldn’t? Like, of course, it’s worth it to have those shared experiences.

We’ve talked a lot about the horror stories, but these are all easily avoidable, and this is not a reason to not get out there. I think everybody should find the people who are on the same page and give it a go.