personal finance

How Do I Plan a Group Trip That All My Friends Can Afford?

Photo-Illustration: by The Cut; Photo: Getty Images

My friends and I are planning a group trip upstate this winter, ideally someplace cozy and fun (probably in the Catskills) where we can hike and cook and maybe go out to a nice dinner or two. This is the first time we’re planning something that involves coordinating an Airbnb, renting cars, and/or buying train tickets. It looks like there are eight to ten of us going and I’m stoked. However, this group is mostly friends from college (we’re all in our early- to mid-20s), and some of us have more resources than others. I want to plan a trip that everyone can afford and that won’t make anyone feel uncomfortable. I’m also not sure how to split costs when some people might come for three nights and others just for one, some are coupled and some aren’t, etc.

How do I accommodate everyone’s budget and be fair without splitting hairs over everything? For what it’s worth, I am probably one of the more fortunate members of the group, so I want to be sensitive but I can probably afford more than others can. What’s the right way to go about this?

Even asking this question puts you miles ahead of most people, including my own friends (and me) when we fumbled through spring break plans in our early 20s. In the decade since, I’ve learned that group trips get better with practice. Done well, they can be magical and relationship-affirming, an exercise in taking care of one another; I recently went to New Orleans with eight friends and was so touched when they grocery shopped, made me breakfast, and then cleaned up afterward that I almost cried with gratitude. (This might say more about the current state of my home life with a toddler than it does about my friends, but I digress.)

Poorly planned trips that disregard budget constraints, however, are uncomfortable at best and ruinous at worst. I learned this the hard way when I traveled with college friends shortly after we graduated. Our accommodations were way more expensive than what I was used to, but I went along anyway because I didn’t know how to back out gracefully (that skill took me a few more years to learn). The wealthier members of the group spent the whole time complaining about the plumbing in our hotel; I was accustomed to staying in hostels, so the fact that we didn’t have to share toilets with strangers seemed like a luxury to me. I came home broke and irritated, and I’ve barely kept in touch with any of those people since.

You’re right to assume that any trip-planning process is going to be sensitive and anxiety-inducing for at least some of your friends. “From the start, do your best to set a standard of kindness, respect, and openness,” says Jennifer Gray, a licensed professional counselor who specializes in financial therapy. “Money is a tricky topic, and you want to make sure that no one feels picked on, even if it’s unintentional.”

That said, it doesn’t have to be weird. “You’re not asking people to share the details of their bank accounts,” she adds. “You just want to allow space for people to speak up about what they’re comfortable paying for.”

One way to create that space is to appoint a “treasurer” who acts as a sounding board for money-related decisions. “If anyone is uncomfortable bringing up a financial concern in front of the group, they can pull the appointed person aside, one-on-one, to decide how to approach it. Whoever that person is, they should be trustworthy and considerate,” says Gray. (Sounds like you’d be a good candidate.)

Gray also recommends broaching the budget question up front. You could start by naming a range, erring on the lower end for the sake of inclusivity; I’d also check some Airbnb prices to make sure your numbers are realistic for what you want to do.

Alternatively, if it seems too aggressive to ask people to toss out hard sums, you could send links to potential rental homes at different price points. That will provide tangible context to anchor the trip’s overall cost and give everyone an idea of what trade-offs they’re willing to make. Maybe it’s worth it to pay slightly more for proximity to a train station so you don’t have to rent cars. Or you might want a smaller house in a cute town so that you can walk everywhere.

If even the cheapest accommodations are too much for some group members, then it’s better for them to bow out now than jump ship at the last minute. Where you stay (and how much you pay for it) will also help guide decisions like whether you want to go out to dinner versus get groceries and cook at home.

As for what else to budget for, an informal poll of my friends (and a quick scroll through the costs of past group trips) turned up the following line items: booze, groceries, shared transportation (car rentals and/or Ubers and cabs), restaurant meals, and tickets for concerts or museums. These costs are important to anticipate, but they also provide wiggle room. You could have a BYOB policy so that you don’t all get stuck paying for the handle of gross flavored vodka only two people drank. You could trade meal responsibilities so that your food-snob friend with a finance job can pony up for a steak dinner while the friend in grad school makes pancakes for breakfast. Or you can just name the food budget you need to stick to and split it equally.

You mentioned a concern about the logistics of sharing costs without overthinking things. This is where technology can do the heavy lifting. You’re probably aware of Splitwise, the app that allows groups to plug in shared expenses and divvy them up equally; when I spoke to Jonathan Bittner, the company’s co-founder and CEO, he said that Splitwise was created specifically for complex scenarios like friend trips. Its website even features a “travel calculator” that parses group expenses when some individuals are staying for different lengths of time and offers various methods for calculating who owes what (people who share a bed might pay less per night than those who get a room to themselves, for example). You can even scan receipts and have people pay itemized bills if they want.

Another great thing about Splitwise is that it slices and dices the total, tells everyone what they owe and who they should pay, and sends reminders to those who haven’t settled up. (It’s linked to Venmo, which has similar features.) That takes the onus off you and your friends to keep track and chase down your money.

Of course, you’re all adults. If you want to go to a restaurant that others can’t afford, they can say no. A simple, “I was thinking of doing X. Any interest?” will suffice on your part; don’t pressure anyone to overextend themselves, but you also have to trust that they can make their own decisions.

And no matter how careful and sensitive you are, some people might get carried away. I remember being at a bachelorette party in my late 20s where a friend confided in me that she had hit her credit-card limit and couldn’t even buy breakfast on our last day. No one wants a friend to be in that position. But ultimately, they have to make the call.

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‘How Do I Plan a Group Trip That All My Friends Can Afford?’