3 generations going on vacation? Let’s set some ground rules first

If you’re planning a winter or spring vacation with your children, parents, or other close relatives, a vacation home can be an affordable way to keep everyone close without worrying about hotel blocks or finding a large suite. But how close is too close? It’s important to set some ground rules and have a few difficult discussions to ensure your trip is easy.

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Benefits of vacation rentals for multigenerational trips

A vacation rental gives multigenerational family members opportunities to bond over shared meals, movies, board games and other activities.

It adds convenience since you can leave for area attractions or restaurant meals at the same time without standing around in the hotel lobby waiting for those family members who are terminally late. It can even give parents of younger children the support they might need – and an extra set of hands — to get out the door on time without forgetting anything. But setting boundaries and creating guidelines for everything from money to shared activities is important to ensure everyone feels comfortable, safe, and welcome in a shared space.

Be upfront about finances

Some families are fortunate enough to have a grandparent cover all costs for a large, multigenerational family vacation. In other cases, adult children might pitch in to treat their grandparents. If you’re splitting the vacation costs evenly, it’s often easier to request separate checks at restaurants or pay for activities separately. But that’s not always possible, especially if you’re negotiating a group rate for a show or attraction.

The last thing you want to do is create conflict or spend time showing your great-grandparent how to set up Zelle because their 25-year-old grandchild never carries cash.

Hazel Rickett CEO of Scotland-based tour company Rabbie’s recommended apps like Splitwise for group trips.

“Using an app makes it easy to track shared expenses in real time, so no one’s stuck awkwardly asking what they owe,” she said. “It’s a lifesaver when the trip is over too, because once we’re all home, we usually only remember the great memories, not who bought dinner on the third night.”

Discuss room arrangements in advance

When you’re booking accommodations, the topic of money is likely to come up again. Does a family with two parents and one toddler sharing a king bed pay the same as a family with two parents and a teen in a room with two double beds? Will children have their own sleeping area with their cousins or other young relatives, separate from their parents?  

“When traveling on a multigen trip, I find it really important to build in a bit of independence. For me, that might mean going for an early morning run, taking time for a walk on my own, or simply enjoying a quiet read in a cafe.” — Hazel Rickett, CEO of tour company Rabbie’s

When my niece and I planned a lake house vacation with three generations of family members, the rental home had a large den with enough beds for seven kids ranging in age from two to 16. Dividing costs was simple, since couples with kids paid more than the couple without younger kids.

But choosing rooms in a vacation rental may not always be obvious. “Families and money issues can be tricky,” Rickett said.

Having an upfront conversation in advance to outline expectations and agree on what’s fair in terms of costs can reduce conflict.  If there’s a wide discrepancy in budgets, booking separate hotels or vacation homes close to each other may be the only solution.

“I like to stay within walking distance so we can meet up easily in the evenings, but [everyone] can be comfortable with the cost,” Rickett said.

Be flexible

Likewise, if you’re planning group activities on varying budgets, make sure everyone is okay with the costs involved.  If not, it’s okay to split off sometimes. For instance, on a Disney vacation, one family with younger children might be excited to splurge on character dining, while parents with teens might be more interested in grabbing a quick-service meal to leave more time for thrill rides.

“Family activities are an essential part of the memories developed on trips, but everyone has different needs,” said HotelTonight GM Ron Sandel, who frequently travels with his four children, ages 10 to 16, along with grandparents and cousins.

You can split up due to budget constraints or interests.

“When traveling on a multigen trip, I find it really important to build in a bit of independence,” Rickett said. “For me, that might mean going for an early morning run, taking time for a walk on my own, or simply enjoying a quiet read in a cafe.”

Parents of young children are likely to want some alone time, giving grandparents bonding time with babies, while teens crave independence away from the crowd.

“Building in flexibility each day and being clear about which activities are optional helps set healthy guardrails and keeps the whole trip running smoothly,” Sandel said.

Set specific ‘non-negotiable’ group activities everyone will enjoy

It’s also okay to establish group activities for everyone. After all, if you aren’t hanging out together, you could have taken separate vacations. But make sure the shared activities are suitable – and fun – for all ages. On our family Poconos vacation, we enjoyed beach days and canoe rides as a group, along with a steakhouse dinner and ice cream at a famous local spot.

Some optional activities included climbing the 20,000-year-old rocks at Hickory Run State Park’s Boulder Field, shopping, hot tub soaks, and long naps (for the adults and the kids. During the winter, depending on the locale, you may want to plan ahead for bad weather and extended time indoors.  

“Conflict arises when the family gets bored, so come up with activities that will keep the family engaged,” Sandel said, noting that his family loves games. “Our favorite travel games are Q-less, Bananagrams and the Imposter app.”

Should you get a hotel instead of a vacation rental?

While a vacation home might be more affordable in the long run, booking a hotel instead can make multigenerational travel easier in some ways, both Sandel and Rickett noted.

“You can book hotel rooms that map neatly to your family’s needs,” Sandel said.  

If anyone in your party needs ADA-friendly accommodations, it’s often easier to find in a hotel. But make sure to ask in advance. Sandel pointed out that meeting multigenerational needs while keeping the family together requires some advance planning.

“I would first think about making sure all the rooms are on one floor to make it easy for family interaction, and even calling ahead for connecting rooms,” he said.

Booking adjoining rooms with grandparents or other adults who can offer a hand with younger children reflects one of the perks of a vacation rental while giving every family their own space.

When you’re ready to go

Whether you decide to relax in a luxurious resort with all the amenities or share home-cooked meals in a spacious vacation rental, being aware of each family member’s unique needs, comfort levels and boundaries is a key to a successful multigenerational vacation. Discuss these factors in advance so there’s no guesswork or assumptions that can lead to conflict.

If resentments arise or bad moods strike, discuss it calmly before the situation escalates. A multigenerational vacation should create memories that make you smile, not lead to strained relationships to navigate at the next family gathering.

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