How to Ensure the Group Chat Makes It Out the Holiday

So the holiday has made it out the group chat… but how do you vacation with your friends without falling out over finances?
Published November 5, 2024

(Image: Slim Aarons/Getty Images)

Congrats. You’ve done it. You’ve rounded up your closest friends, synced your calendars and somehow found the only free window in the entire year when the stars perfectly align, and you can finally all go away together.

But, now the flights have been booked and holiday ’fits are coming together, it’s time to consider the next big step: how the hell do you get there and back without falling out?

Of all the disputes trips away can throw up, financial fights are the stickiest. Nothing kills the relaxed, sunny vibe more than a disagreement over who’s paying for the next round of rosés or the taxi to the hotel. So, how do you make sure the messiest night of the trip is confined to the club? Or stop resentment from rearing up when you’re still chasing IOUs after it’s wheels-down back home and the holiday buzz has worn off?

To help, consider adding these expert-approved tips to your itinerary.

Related: Going Through a Friendship Breakup? Here’s How to Navigate It

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how to holiday with friends...

Create an anonymous budget poll

The good news is that you can prevent most major cash blips before the trip even begins – or, more specifically, before you book the holiday. It’s important to be transparent about costs from the get-go, says financial expert, author and influencer Clare Seal, who reckons that this is a common problem with hens’ parties in particular.

It goes without saying that you need to book a destination everyone can afford. An easy method to make sure the entire group is happy: setting up an anonymous poll for the budget at the same time as you select dates. Then, without prying into anyone’s finances, simply select the lowest figure, Clare advises.

Related: Here’s How Much Australians Your Age *Actually* Earn

Don't do your friends dirty

When it comes to shared accommodation, be mindful everyone is paying a fair price. Sure, splitting the cost is easy, but it may become a problem if your friend in the single room resents the pal living it up in the master suite for exactly the same. 

Dividing the price proportionally is often much fairer, as Clare points out, and you may find someone is keen to save cash while another guest is happy to pay for an upgrade. When it comes to settling the bill, remember, “Not everything you do has to be super transactional .” Something as simple as buying your mate’s dinner if you have a larger room may be the solution, says Clare.

Apps are your friend

Simplify spending during your holiday by creating a shared digital wallet and using the group pot to cover daily expenses. You can do this through apps such as HyperJar, Splitwise or PayPal.

Nominating one person to pay for everything could work, but be wary, there’s scope for bad feelings. Either way, if payments are due, make these in advance or on the day—but certainly no later, explains author and chartered financial expert Makala Green.

Set up regular check-ins

Makala recommends scheduling in finance check-ins before and during the holiday. “Managing a group can be very difficult. Once something is agreed, it doesn’t always stay that way.” So it’s worthwhile checking if everyone’s still on the same page at regular intervals. Is the group still happy with how money is being spent? Does the budget need to be adjusted if a dinner ended up costing more than expected?

Stick to your financial boundaries

This rule applies at every stage, from planning to poolside cocktails. Set your financial boundaries with confidence. You don’t owe anyone an explanation, says psychologist Tara Quinn-Cirillo. You should remember that being assertive is different from being aggressive, and a good friendship is one that gives you space to be heard and not judged, she advises.

That said, if you’re nervous about discussing money, you can always confide in one pal before chatting with the wider group, Dr Quinn-Cirillo notes. We can’t guarantee it will be easy—shame is often attached to the topic of money—but it does get easier having those conversations, she reassures. And often, your mates are feeling money pressure too. “You will be surprised to find that your friends probably have the same worries,” Dr Quinn-Cirillo says.

Start planning ASAP

If your friends share the same vision for your getaway but affordability is the issue, start planning your next holiday straight away. You could suggest getting everyone to set up a monthly direct debit that’s going into a single bank account just for the trip. And it doesn’t have to be a huge amount, but it does need to be an amount everyone can afford.

“Even if someone does earn less, if you’ve given them enough notice, they can enjoy the things that someone on a bigger salary can,” reasons Makala. Don’t forget to take advantage of any discounts you might get from airlines and hotels when making a group booking, too, she adds.

Related: Fancy a Career Change? These High-Paying Jobs Are Pretty Low-Stress

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This article originally appeared in Issue 02 of Cosmopolitan Australia. Get your copy and subscribe to future issues here.

Amber O’Connor
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