Vacationing With the Grandkids: What Could Go Wrong?

Grandparent relaxing in the pool with his grandson

(Image credit: Getty Images)

Vacationing with the grandkids (without their parents) could be one for the ages or an absolute nightmare, which is why you should carefully consider it before planning your skip-generation trip.

Known in some travel circles as "gramping," taking your grandchildren on vacation, domestically or internationally, is a bucket list item for many retirees. After all, who doesn’t want to spend quality time with their offspring?

“Gone are the days when the typical extended family all live in the same neighborhood. Today, many families are spread out across the country or the globe, making skip gen travel a great option for bonding with grandchildren,” says Julia O’Brien, vice president of marketing at Tauck, an upscale guided tour travel company. “If a grandparent is seeking to reconnect and share meaningful experiences with their grandchildren, time together exploring new parts of the world can be one of the most meaningful ‘gifts' there is.”

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AARP’s 2025 travel trends survey found that 56% of travelers 50-plus said their motivation for travel is to spend time with family or friends.

Sounds majestic, right?

But it's not for everybody. Your temperament and that of the grandchildren are a big factor in whether this type of travel makes sense. The same goes for your health and finances. Chances are, if you’re taking the grandkids on a trip, you are also covering all the expenses involved.

Still on board?

Before you book a vacation with the grandkids, here is a look at what could go wrong on your gramping trip.

1. Road trip dangers are everywhere

Going on a road trip with the grandkids isn’t as simple as hopping in the car, filling it up with gas and hitting the road. There are many dangers you may encounter if you don’t prepare for them in advance.

Take your tire pressure for starters. Making sure it is at the right pressure may not seem like a big deal but if you are among the millions who don’t regularly check it, you could be in for a flat tire or worse a blow out while you are on the road with the grandkids, says Robert Sinclair, a spokesman for AAA Northeast.

“About 80% of people are driving around on improperly inflated tires,” says Sinclair. “They tend to be under-inflated, which is very bad.” If you have to pull over to change a flat tire, that has its own dangers. “We lose two truck drivers every two weeks in the U.S. being broken down on the side of the road,” says Sinclair.

It's also important to ensure you have enough windshield wiper fluid and new wipers installed. The last thing you want is to be stuck in a rainstorm and not be able to see the road ahead of you.

The same goes for having proper directions. You don’t want to get lost in an unfamiliar area, which could quickly put a damper on your gramping trip.

2. You blow your vacation budget

Many grandparents have a fixed income and have a budget for everything, including vacations. That can quickly fall to the wayside when traveling with the grandkids.

It's natural to want to spoil them, but it can add up if you aren’t careful. That would undoubtedly ruin the trip if you’re worried about the expenses. Plus, once you're back, you’ll have to figure out how to cover the lost income or pay the credit card debt.

“It’s a good idea for grandparents to explain expectations during the trip that way grandchildren can know what will and won’t be allowed,” says Nicole Gill Council, travel editor for AARP.org.

“It’s also a good idea to include grandchildren in the planning process so they can select activities or destinations based on their interests. When that happens, grandparents won’t be tempted to spend on additional activities.”

3. The grandkids are bored

Vacation is supposed to be fun, but the definition of fun is wildly different for grandparents and grandchildren.

The last thing you want is to have uninterested grandkids, especially if you paid an arm and a leg for the tip.

“As one grandparent told us years ago: ‘The goal is, at the end of the trip, everybody comes back and says they had an absolutely terrific time,’” says O’Brien.

If you run out of fun things to do or talk about, the trip could fail. So much for everyone coming back saying they had a terrific time!

4. You didn’t take accessibility into consideration

That old saying “I need a vacation from the vacation” couldn’t be truer when traveling with children, especially ones of the younger variety.

If keeping the grandchildren entertained requires a lot of walking or activities and you aren’t prepared or have mobility issues, that could quickly ruin the trip.

"If there are no elevators, a lot of stairs or cobblestone roads, those with mobility concerns may not be able to fully participate in the vacation,” says Council.

It applies to the grandchildren, too. If you don’t schedule in enough breaks or downtime, you could end up with cranky, overtired kids on your hands. Keep in mind, many vacation places that are great for wheelchair users are also great for kids.

5. Lack of proper documentation

Flying with grandchildren or taking them on an international cruise comes with a lot more requirements than a road trip stateside.

You may not be able to get on your flight if you don’t have a notarized letter of consent or you may not be able to make health decisions for them if you don’t have a medical consent or child medical release form. This is a legal document signed by the child’s parents or legal guardians granting grandparents the authority to make medical decisions for the minor.

“Border officials can be extra vigilant about children traveling with adults who aren’t their parents,” says Council. “Grandparents should also check airline policies on family seating, which would allow families to sit together on a plane without paying extra fees.”

It's not all bad

Sure, some things can go wrong when traveling with your grandkids, but there are also many benefits. Preventing the trip from going awry requires planning, flexibility and a budget.

“Traveling with your grandkids is all about embracing the moment, and sometimes the unexpected," says O’Brien. “Keep an open mind, stay flexible, and remember that the best memories often come from the little surprises along the way. Most importantly, enjoy the journey, these are memories they’ll remember forever.”

Donna Fuscaldo is the retirement writer at Kiplinger.com. A writer and editor focused on retirement savings, planning, travel and lifestyle, Donna brings over two decades of experience working with publications including AARP, The Wall Street Journal, Forbes, Investopedia and HerMoney.