Planning a group vacation with friends? Read this first so you’re still friendly after the trip

Some of the best — and worst — holidays I’ve been on have been with groups, and in almost all cases there were two deal breakers: how the bills got handled, and how the precious time got spent (also related to the bills, BTW).

After two years of limited to no group-travel experiences, and with most mandates pretty much lifted, just about everyone wants to sip mojitos on a beach somewhere in the company of their closest friends.

The benefits of group travel are huge — time to reconnect, money can be saved by booking and buying things together, and extra hands to help with kids (if you’re a busy family).

But the success of your group vacation will depend on the money and time expectations you set together. If you don’t take the time to carve out these boundaries, you could be in for a miserable holiday.

Who’s paying for what?

Are you splitting the VRBO evenly or is one person/family paying for the majority of it because they get the master suite. Have the taxes and fees been accounted for in your bookings? Is one person responsible for paying the entire set of costs (flights, food, accommodations and entertainment), and then expecting to be reimbursed for it? If so, do they want cash, an e-transfer, gift cards? Is part of the holiday a gift (bachelor parties, for example)?

Get clear on costs by making a shareable spreadsheet. Populate the cells with all the costs you can possibly think of. Then, start talking — who’s paying for what, when is reimbursement expected, and on it goes. Honestly, I wouldn’t advise clicking the “book now” button until you’ve done this work.

If you’re out buying dinner or tickets for the aquarium, the easiest way to keep things even is to split the bill precisely how everyone ordered. Just ask for separate checks up front and have each person pay for their own tickets.

The best practice is to promptly reimburse the person who has paid upfront — like, within 24 hours.

Think twice about travelling with a cheapskate or a wild spender
I can’t stress this enough: If you know your pal and you are not on the same page about what you want to spend, don’t travel together. The best example is the case of the cheapskate traveller who prefers to sip free water and mooch leftovers (the chicken wing stealer), rather than participate in and pay for their portion of the group dinner you all planned. They will also seriously cramp your style when it comes to paying for certain experiences, like going to a baseball game vs. watching it on TV from your Airbnb.

There’s a flip side to this — the crazy spender. These people have no financial constraint, especially after a few drinks. They are the people who order the champagne tower for $450 and expect you to pay for half, whether you agreed to it or not. These social spenders have a way of tripling your planned holiday budget, and the reality is they can’t actually afford to spend like this, and are using credit.

How do you want to spend your time?

What do you all want from the travel experience? Are there events or activities you want to do (or not). Is the goal relaxation, partying, family time, adventure? Is it totally OK if you all do different things during the day and come together in the evening (this can be helpful when the travellers have different budgets)? Not everything needs to be preplanned or programmed, but it can be helpful to be clear about how you generally want to spend your time, and be clear on costs for activities. Personally, I hate having every moment planned out because it doesn’t leave room for spontaneity; one of the beautiful gifts travel offers. I think it’s worth noting that there are hundreds of free activities for groups — beach days, hiking, running, picnics and so on.

What are the boring obligations (if any) from each person?

Who’s going to do the dishes or laundry? Is there a designated chef? Is one person responsible for the meal planning, restaurant bookings or gas tank filling? Who’s going to take care of the kids if the adults want to go for dinner? Do any of these duties have financial considerations including paying a babysitter or paying more at the pump for surging gas prices?

Planning to party like it’s 1999? Watch your wallet.

I completely understand wanting to blow the doors off while vacationing this summer, but a little restraint might be a good thing. We are in uncertain economic times due to rising interest and aggressive inflation, which could change your level of financial security in the not-so-distant-future. Do what’s right for your budget, and know that it is 100 per cent OK to spend money on travel, in a financially smart way.

If this article is causing you a financial or relationship headache or quickening your pulse, you might want to consider travelling solo.

This article was originally published in The Star. Lesley-Anne Scorgie is a Toronto-based personal finance columnist and a freelance contributing columnist for the Star.