How to Handle Awkward Money Situations on a Group Trip

Someone flew in for the group trip a day late, so should they still pay for yesterday’s hotel night? Someone else doesn’t drink alcohol, so do you split bottle service costs if they still sat at the club’s reserved table? Meanwhile, someone else really doesn’t want to pay for their own matching T-shirt that everyone else agreed to, which is sure going to look goofy in the family photo.

Family reunions, bachelor or bachelorette parties and other group trips can be rewarding. But if people aren’t on the same page financially, that can lead to arguments or resentment.

Group trips are on the rise. Hotel company IHG said it expects strong growth in 2022 among social, military, education, religious and fraternal groups traveling to its hotels. And wedding website the Knot predicts that 2022 will see a more than 20% increase in weddings versus 2021.

That means plenty of opportunities to travel with friends and family (not to mention plenty of opportunities for encountering awkward money situations).

There’s no one-size-fits-all approach to answering each awkward money situation. But there is one method that — if done correctly — can prevent awkward money situations from ruining your group trip: communicating in advance.

Treat your vacation relationship like a marriage

Most people don’t like discussing how much money they make, have or spend with people besides their partners or spouses — and even that can be difficult. But you should treat fellow financial decision-makers for your trip like you would treat a potential spouse: Be open about each other’s budgets, and know what you’re getting into.

Communicate budget preferences before you commit

Be upfront about how much you’re willing to spend, who is paying for what, and what you do or don’t want to pay for. You don’t necessarily have to agree, but have a plan for when you disagree.

If your priorities differ so drastically that you can’t agree to disagree, then it’s also OK to back out of the trip.

Decide which finances to merge vs. separate

Joint versus separate finances: Either can work in successful partnerships, and the concept applies to trips, too. Just make sure you decide whether receipts will be pooled evenly or not before you book the trip.

The joint finance method can keep things simple (e.g., everyone stays at the same hotel). But it can lead to bitterness if priorities differ, like if someone wanted to splurge on a fancier hotel than you settled on. Both can work, as long as you understand the trade-offs.

You can even do a mix of both. Everyone might book their own flights so one person can fly first class even if someone else can settle with basic economy. Meanwhile, you might agree to split the vacation rental and groceries that stock it.

Have a plan for common travel scenarios

Everyone’s relationship with their finances is as unique as their relationships with their friends and family.

So, while there’s no right way to solve every money situation, here are some common ones.

Problem: You can’t keep up with everyone else’s spending habits

Solution: Split up for a bit.

Be upfront if someone else’s vacation priorities or budget don’t align with yours. Maybe someone prefers caviar and champagne while you’d prefer the budget-friendlier hole in the wall.

It’s OK to dine separately, then exchange stories about your experiences later.

Splitting up can also help avoid spending money on something you won’t enjoy. Even if you technically can afford it, don’t let your buddies guilt you into a Michelin-starred meal you’re just not that into. Explain that you’d prefer to prioritize certain purchases over others (and accept that they might not join in on your spa day or in the first-class seating, either).

Problem: Someone isn’t getting the full benefit of a split cost

Solution: Defray costs elsewhere.

When splitting costs, not everyone will derive equal value down to the last cent. Accept that one person will always eat at least slightly more at the family-style meal, while only one person can likely take home the leftovers.

But in other scenarios, it can be clear where someone didn’t get the full benefit of a split cost (e.g., a shared meal when someone doesn’t drink or a vacation rental where someone got the master suite while someone else got the couch). What’s less clear is how to split the cost.

You could summon the Mathlete team to help calculate how to split the bill (there are also apps that do this, like Splitwise). That can make sense for relationships where the preference is to split things evenly, down to the last penny.

Otherwise, use your best judgment to compensate people who didn’t get as much value as others. If the nondrinker at dinner is also the designated driver, consider covering their meal completely. If someone arrived at the vacation rental a couple of days later than everyone else, consider splitting the cost of the home, but letting them off the hook for the grocery bill (after all, they’re likely partaking in less food, too).

Problem: A companion wants to pay for group expenses with points

Solution: Come up with a reasonable price tag.

Travel and credit card points are certainly valuable, but they’re not exactly a real currency. You’re likely not going to pay someone back in points. While NerdWallet has put in extensive work to assign value to your points, it wouldn’t feel quite right to assume that — just because the 100,000-point trip you booked is worth, say, $2,000 — your travel buddy should reimburse you $1,000. So even if you do have perks with a nicer hotel, you might want to evaluate if the overall hotel price is still worth it for the group

Still, you might not necessarily want to skip booking on points in lieu of cash, as points bookings often entail additional benefits, like flexible cancellation policies or waived resort fees.

Instead, communicate and agree on what the points are worth ahead of booking.

• You could calculate the trip’s cost in cash and have your buddy pay half that amount. But that can feel iffy if you’re staying at, say, a $1,000-per-night Hilton resort booked through a free night certificate that you earned on a credit card with an annual fee much less than that.

• You might factor in the opportunity cost of earning those points. Perhaps you got the points through a sign-up bonus on a credit card, but the card has a $500 annual fee. Consider asking your buddy to cover part of the credit card fee.

• If you got the points at no cost — perhaps they were granted through work trips booked on your corporate card — you might just “donate” them to the group trip.

As a receiver of such bookings, consider finding a way to say thank you, such as paying for the meals of the person who provided the points.

Accept that awkward money scenarios are inevitable

Successful partnerships require compromise — as do group trips. Your budget-conscious friends might want the red-eye flight, and now you’re delirious from coffee overload and insufficient sleep. Conversely, you might find yourself funding things you didn’t want, like a private cabana.

You’re probably not going to get away with sitting on the regular pool deck while everyone else indulges in their shaded champagne showers. Accept that some unwanted costs are inevitable. Rather than cringe at how much you’re spending, remember that you’re spending time on new experiences with people you love, perhaps clad in matching outfits to boot.