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I'm disappointed my son can't make it, but we can't reschedule. I want him to feel we are treating him fairly.
By
Maurie Backman
published
29 March 2026
in Features
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Question: We want to treat our adult children and grandchildren to a 10-day cruise to Greece, where I'm from. Our daughter said yes, but our son’s career is at a peak and he can't escape. I want to make things fair, but I can't reschedule. Should I send him a check?
Answer: It's not a given that you'll have more wiggle room in your budget in retirement than during your working years. But if you built a large nest egg and have modest expenses, you may have the ability to cover the cost of shared family experiences, including travel with your grown kids and grandchildren.
Plus, if you have retirement accounts that are subject to required minimum distributions, there's perhaps no better way to make good use of those forced withdrawals than to treat your extended family to an amazing trip. That could mean embarking on a 10-day cruise to your home country of Greece, where you can introduce your loved one to the sites and culture you grew up with.
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Sign upMulti-generational trips are becoming more popular these days, with 71% of grandparents having taken one recently and 57% of grandparents anticipating one in the future, according to a joint study published by NYU. And while they do need to be carefully planned, they can also be extremely rewarding — more so than traveling with just a spouse or partner.
But what if your generous offer to take your adult children and grandchildren on a 10-day cruise to Greece doesn't work for everyone? It may be that your daughter has a flexible schedule, but your son is too busy at work to get away for that long.
In an effort to make things fair, you may be inclined to send your son a check to make up for the fact that he can't attend. But your efforts to even things out may end up causing more problems than intended.
You're better off doing something more meaningful
As a parent, it's natural to want to treat your kids equally. Often, family conflict arises when one sibling feels the other is favored in terms of time, love, or money.
If you're treating one of your children and their kids to a 10-day cruise, there's an obvious cost involved. And you may feel that the "fair" thing to do is to send your son, who can't attend, a check roughly equivalent to what you're spending on your daughter's participation. But Eric Croak, CPF and President at Croak Capital, advises against that.
"While I completely understand the knee-jerk emotion behind wanting to send a check to even things out, I think it can create an awkward precedent going forward," he says. "If you put a price tag on an experience, every vacation, holiday, or family gathering from here on out may suddenly become something that needs to be cash-out refunded for the child or children who can’t make it. And that expectation can be hard to undo."
A better approach, says Croak, may be to decouple the experience from any kind of monetary gift. After all, you're presenting both of your children with the same opportunity. It's not your fault that your son can't attend and your daughter can.
That said, Croak thinks it's not a bad idea to try to do something nice for your son in light of his inability to go on the trip. But in that case, make it a standalone gift or gesture.
"Contributing toward something just for him — perhaps a Roth IRA contribution, a large purchase he’s talked about making, or even a smaller trip that he can take with his family whenever he’d like — could end up feeling really intentional and special," he says.
Croak says that if you go this route, the amount of the gift doesn't need to match the cost of the cruise.
"In fact, trying to exactly match that dollar amount may do more harm than good," he insists.
"The money is the easy part; the relationship is what’s important." — Eric Croak
Focus on the relationship more than the trip
It's unfortunate that your son can't get away from work to participate in a memorable family experience. But sending him a check for the equivalent of what you would've spent may not be a well-received consolation prize, says Amy Bishop, Licensed Marriage and Family Therapist and owner at Springs Therapy.
"Doing so says that the value of the trip is the monetary investment, as opposed to the real gift of leisure time with family and a cultural trip to the parent’s homeland," she says.
Bishop, like Croak, recommends asking if there's something that would be equally meaningful to your son as the proposed trip. It may not be money he wants, but rather, your time. That could mean helping with child care during the year or over the summer, or simply taking a scheduled trip with you at a different time that better fits his schedule.
Your family should also think of ways to let your son know he is missed during the cruise. You (or the grandkids) could make a short video for him, call him frequently or make cards to send to him when you land. Since you are from Greece, make sure to send him stories and pictures from the trip that relate to your family history.
"I have heard despondent sentiments from clients I've worked with, such as 'my parents loved me with money, not time together or emotional support,'" Bishop explains. "Though it is kind to be intentional about balance, it's important for these parents to recognize that money by itself does not help relationships."
Croak agrees and says validating your son's feelings about having to miss out on the experience is important for your relationship.
"In the grand scheme of things, the money is the easy part," he says. "The relationship is what’s important. And as long as you both understand each other’s intentions moving forward, I doubt resentment will develop."
Do you have a tricky money situation? We want to hear about it for an upcoming advice column. We're interested in retirement-related financial dilemmas, especially those that impact relationships with partners, friends and family. You will remain anonymous. Submit your question to [email protected]. Not all questions will be published.
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Maurie BackmanContributing WriterMaurie Backman is a freelance contributor to Kiplinger. She has over a decade of experience writing about financial topics, including retirement, investing, Social Security, and real estate. She has written for USA Today, U.S. News & World Report, and Bankrate. She studied creative writing and finance at Binghamton University and merged the two disciplines to help empower consumers to make smart financial planning decisions.