6 Tips For Planning A Multigenerational Vacation, According To An Expert

I’ll admit I had some trepidation when our group of 12, ranging in age from two to eighty, descended upon Turks and Caicos last Thanksgiving. Sure, I was excited about spending time with my sister-in-law who lives across the country in San Diego. And who doesn’t love drinking a cocktail on the beach in November? But my husband and I would be sharing accommodations for a week not only with our two preschoolers and my two college-aged stepchildren, but also with my sister-in-law, her two children, her boyfriend, and my in-laws. Luckily, our advance planning and open dialogue helped craft an itinerary that kept everyone happy—for the most part.

Here’s what I learned about how to plan a successful multigenerational vacation, plus advice from a professional.

Meet the Expert

Mickie Simon is a licensed clinical social worker based in Washington, D.C.

Plan as Far Ahead as Possible

Executing a vacation with grandparents, siblings, and children requires more advance planning than your run-of-the-mill trip. You’ll want to plan as far ahead as possible, up to a year or more in advance, to maximize the coordination of everyone’s work, school, and custody schedules.

In my extended family, for example, we have to navigate two sets of custody schedules—my husband’s and my sister-in-law’s. Before plotting out our trip to the Caribbean to celebrate my father-in-law’s 80th last year, we confirmed that all the kids would be able to join for Thanksgiving week. We also consulted our respective work schedules and school calendars to ensure the trip was feasible.

Relatedly, be realistic about the ideal length of a joint vacation for your individual family. Maybe you routinely spend two weeks together every summer. Or perhaps tensions start to rise after a long weekend.

“On a multigenerational trip, there’s the possibility of building communication skills by having time and space for more meaningful conversations in a less stressful environment than family holidays and gatherings,” says Mickie Simon, a licensed clinical social worker based in Washington, D.C. “That being said, I’m a big believer in shorter experiences that are more successful.”

Agree on Cost in Advance

When you’re traveling as part of a group, it’s essential to discuss costs in advance so that everyone feels comfortable participating in the trip. Not only do individual households likely have unique financial situations, but people are also bound to have differing ideas about what they feel comfortable spending on a vacation.

Related: 24 Affordable Family Vacations You Haven't Thought Of Before

We know that talking about personal finances can feel awkward; this is true even among families that have close relationships or where money is plentiful. Here are some questions you can ask each other to facilitate a discussion about vacation costs:

• What is our overall budget for this trip?

• Will each household pay for their own airfare or other transportation?

• How will we split the cost of accommodations, particularly if they are shared such as in a home or apartment rental?

• How will we cover the cost of meals?

• Will each household cover their own entertainment costs?

• Is part of the trip going to be gifted by one or more of the attendees to other participants, and if so, is everyone comfortable with that approach?

Hammering out these details in advance will prevent discomfort and difficult conversations later on, ensuring the focus of the vacation remains enjoyment rather than squabbling over who’s covering the cost of dinner.

Select a Destination that Works for Everyone

Just because you grew up visiting a particular destination every summer or spent winter weekends on the ski slopes, don’t assume those same rules apply now. Things change as individuals get older, other adults and young children enter the picture, and parents age.

“Families should consider what they like to do together, how active they like to be, and whether they are capable of compromise and giving everyone a say in the planning,” says Simon.

For my family’s trip to Turks and Caicos, we reached out to a travel agent we had previously worked with to relieve the research burden from a single individual. We gave our agent an overall budget for accommodations and meals, our travel dates, our preferred accommodation type, a breakdown of how many individual rooms we would need to feel comfortable, the U.S. cities from which we would each be flying, and the types of activities we enjoy doing together. I can’t emphasize enough how helpful this was in identifying a destination that worked for every member of my family in terms of activities, accessibility, and overall budget.

Be Flexible, Especially When People Choose to Opt Out

Flexibility is key, especially when traveling as part of an extended clan. “There might be different levels of interest in certain activities and the pace of the day,” says Simon. This is especially true for multigenerational families with a wide range of ages. Younger children may need to follow a set nap schedule or take routine jaunts to the playground, teenagers might want to sleep in, and grandparents might have limited mobility.

“Decide which things everyone wants to do together and if there will be times to do things separately,” says Simon. “Having clear expectations about how much togetherness is expected helps when people choose to opt-out.”

In our family, for example, we took a more inclusive approach with the understanding that there might be times when individual households chose to opt-out. We included everyone in our dining and activity reservations but intentionally built-in opportunities for family members to do things on their own, like grab breakfast or take a dip in the pool.

Plan One Special Activity that Everyone Can Participate In

A highlight of our trip to the Caribbean was a professional photo shoot that my husband, sister-in-law, and I gifted to my father-in-law for his milestone birthday. Of course, there was some angst among the group about how to dress and griping from the teenagers about the early morning timing of the shoot. At the end of the day, though, we had fun together while doing something to preserve the memory of a once-in-a-lifetime experience.

Whether it’s a photo shoot, excursion, or celebratory meal, try to plan one special activity with the whole group during your vacation. Doing so can even reap long-term benefits. “Sharing moments of joy builds goodwill and we are less emotionally reactive with people we love when we have a reservoir of goodwill,” says Simon.

Make Time for Yourself

Even under the best of circumstances, traveling with family comes with a certain level of stress. This is especially true for the individual who takes on the role of the planner and finds themselves fielding daily questions about where the dinner reservation is or where folks should gather for an excursion.

One of the best antidotes I’ve found to feeling overwhelmed on a family vacation is to prioritize time to decompress. Even if it’s just a short walk along the beach or an extra cup of coffee by myself after breakfast, I try to carve out time alone. Do yourself a favor by working that solo time into the itinerary and letting your family members know in advance so they can do the same.

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