How to split costs with vacation freeloaders and keep healthy relationships

The time away has given us a great way to bond. It can do the same for you.

But so much can go wrong on group trips. If you don’t want to end up paying more than your fair share on a shared vacation, your planning has to include some financial discussions.

Here are six money tips if you’re going to invite people to vacation with you.

Clearly communicate the costs

If talking about money makes you uncomfortable, you might be better off vacationing alone. Family and friends can test your patience, especially regarding financial issues.

Over the years, I’ve heard from readers fuming over expenses they were left to cover, like when a couple had to pay a $150 fee when their traveling companions left a mess in a timeshare villa.

Others have complained about people not bringing enough cash or forgetting (sometimes on purpose) to include tipping in the calculations of what they owed. They put up with one person ordering enough food for two and then being the first to want to evenly split the bill.

If you’re going to share your time off, lay down the law. Before you board the plane or hit the road, schedule a call or meeting to discuss all the expenses and who is covering what.

Here’s the script to start the talk: “Hey fam (or friends), we want this to be an enjoyable experience, and for that to happen, we need to be clear about the costs.”

Then, you should give them a breakdown of everything, including transportation, lodging, food and the price for excursions, entrance fees or sightseeing tours. This requires a well-researched budget.

Compromise on cost-splitting

For our family trip to Mexico, my niece and her husband brought their two small children. As a group, we decided not to count the children in dividing the villa’s cost. It was an example of us trying to be reasonable.

If there are nonalcoholic drinkers, you shouldn’t expect them to split the cost of the bar tab.

As an older adult, you might be able to afford contributing more money for certain expenses because you’ve been working and saving longer than younger adults on the trip. It’s what my husband and I do.

As a related point: Please consider other people’s financial situations. Ask folks what they can afford, and because it’s a group trip, be willing to compromise on your vacation planning to fit their budget.

It’s probably no surprise that I’m the banker on our vacations. I keep track of what’s being spent and what’s owed.

The banker must be diplomatic but firm when collecting money, and also be someone who can negotiate for the group.

If you are traveling with an extremely large entourage, it may not be possible to divide the cost with everyone putting their share on a credit card. Increasingly, many vendors are cashless — or a deposit may be needed before everyone has an opportunity to kick in their share.

If you decide to pay for the group, make sure you can afford the responsibility. If you can’t be paid right away, make it be known that failure to pay later will mean they won’t be invited again.

Thank goodness for the many payment apps that allow you to split costs, such as Zelle, Cash App, Venmo and PayPal.

If you have to pre-book tours or excursions, or rent a vacation home, get the money upfront — no excuses. Set a deadline for when the cash is due. If someone lags, they are left out, full stop. Don’t tolerate slackers. It will train people to believe you when you set payment due dates.

If they miss the cutoff, you still can be kind: “I’m so sorry, but we had to commit, and you weren’t on time.”

There are some who might play on your emotions, pledging: “You know I’m good for it.” But you know full well they aren’t reliable or financially responsible because they have a history of not making good on a promise to pay.

It’s one thing to be generous by sharing your vacation or vacation home, but don’t let people take advantage of your generosity.

Construct a financial wall

Let’s say you’ve invited a family to join you on a vacation at a timeshare resort, which requires guests to put a credit card on file.

When you check in, have the family members or friends traveling with you put up a credit card. If they are in a separate villa, even if the reservation is in your name, do the same thing. As you speak to front-desk personnel, let them know that any charges for extra cleaning or breakage incurred in their villa will be charged to their card.

If you’re dining out, ask before the meal is served if you can get separate checks.

You shouldn’t be timid about your expectations of what they should cover. If you choose to stay silent and have to pay more than you should, that’s on you.

Communicate clearly your traveling style and budget

I don’t like to overschedule my vacation, especially with expensive, crowded excursions. I like to sightsee but also want to chill. I don’t necessarily want to spend a lot of money eating at a five-star restaurant that’s all the rage. My happy place is just sitting on a beach, listening to the crashing waves.

However, your traveling companions may want to see as much as possible, including the tourist traps. Let them go — on their own dime and time.

If you can’t afford to do as much as others, say so. Here’s another script: “We have a tight budget, and while we would love to join you, we’re going to sit this one out.”

If you have the means to splurge, don’t make your companions feel they’ll be missing out. Do not say: “You may never be back here again, so you have to go.”

Vacation sharing can be great, but without these candid conversations, you’ll bring home the emotional baggage of a spoiled summer trip.

If you want more personal finance advice that’s timeless, order your copy of Michelle Singletary’s Money Milestones.