Family vacations might be the best setting to talk to your kids about money

Anup and Nitin Kaushal have been travelling with their three children for as long as they can remember. When their kids were young, family trips were easy to co-ordinate – school breaks dictated the timing, and no one complained about squeezing into one hotel room.

But as their sons and daughter entered their 20s and 30s, with careers and relationships pulling them in different directions, organizing an annual trip became more challenging. Still, the Kaushals, who live in Richmond Hill, Ont., made it a priority – not just for the memories, but for the conversations that tend to unfold on these trips.

“When you’re on vacation, everybody’s together,” said Ms. Kaushal. “You eat together, plan together, and talk about things you might not at home because you’re in a different environment,” such as relationships and career decisions.

Now that she and her husband are nearing their 60s, a big topic they discuss while on vacation is what their kids’ financial futures might look like after the parents are gone.

Experts say the Kaushals are not alone in this approach. More families are discovering that thoughtfully planned vacations are a way to ease into difficult conversations around estate and succession planning. Away from the pressures of daily life, these trips offer a neutral, low stress setting to talk about the future.

Amid the stress of day-to-day life, it can be hard for families to find the right moment to have these discussions. But on a vacation, “everyone’s relaxed and has their guard down,” said Jeff McCartney, a certified financial planner based in Markham, Ont.

When that happens, “you can actually bring up more serious topics,” such as succession planning, he said. “You’re unwound and open for any kind of conversation.”

That ease matters, because for many families, succession planning remains an uncomfortable subject and is often avoided. A 2023 Sun Life survey found that while 44 per cent of boomers plan to leave an inheritance, less than half of them have a formal estate plan. A quarter of them haven’t even discussed their intentions with their children. That silence can lead to confusion, resentment, and in some cases, legal conflict down the road, Mr. McCartney said.

Not only are family getaways an opportunity to have conversations, but it makes those discussions easier by reinforcing shared family goals.

Without regular connection, adult children can drift from one another, and from their parents’ values, said Greg Moore, a partner at Richter Family Office. That distance can make financial decisions feel impersonal, and disagreements more likely.

Family trips help re-establish those bonds, laying the groundwork for co-operation later, he said.

“The best piece of advice that we typically provide to families who are concerned over things like wealth transfer and entitlement is to spend time as a family to develop that value set,” Mr. Moore said.

In some cases, travel even becomes a formal part of the family’s inheritance strategy, said Anna Judek, owner of Zebrano Travel, a Toronto-based luxury travel concierge. About 25 per cent of her bookings are multi-generational family trips, she said, and often families set aside money specifically for travel in their estate plan.

These families see trips as an “investment” in family cohesion, not just a vacation, Ms. Judek said.

To make these trips work, families need to plan well in advance – sometimes a year or two ahead – and be thoughtful about everyone’s needs. Ms. Judek recommends involving younger generations in the planning process to foster buy-in.

In her experience, older family members typically cover major costs, such as flights and accommodation, while younger ones chip in for outings and excursions, but it varies depending on each family’s financial situation.

A common mistake in planning a family trip is assuming that a weekend at the family cottage will offer the same benefits, Mr. Moore said. “There’s always some underlying conflict or tension that often happens when you bring multiple generations in under one roof,” that is familiar to them, Mr. Moore said. A neutral environment allows everyone to come in on equal footing, without old dynamics getting in the way, he said.

Although finances can be hard to talk about, it’s important for parents to have these discussions with their kids while they’re alive, rather than having the kids “go to war” with each other after they’re gone, Mr. McCartney said.

For the Kaushals, their yearly family trip is an intentional way to keep their children close and ensure they continue making decisions together, long after their parents are gone.

“The last thing any parent wants is for their kids to fight over money,” said Ms. Kaushal. “As long as we can still do it, we’re going to keep planning these trips.”