How to plan a multigenerational family trip

Apr 20, 2022

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After the past few years of travel restrictions and family separations, finding ways to travel and reunite with loved ones at the same time can deliver quite a two-for-one payoff. Multigenerational trips are an increasingly popular travel choice for many extended families.

Although multigenerational travel can be immensely rewarding, these trips can be more complicated to plan. With more people on the vacation, there are more travel interests to please and potential limitations to consider.

If you are considering a vacation that spans the generations, you’ll likely need to plan and prepare a little more carefully than you might with a trip with just your immediate family. Here are tips on how to make it happen.

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Why travel with multiple generations?

Before diving into how to plan a multigenerational trip, it’s important to assess whether this form of travel is right for you. Not everyone gets along with their extended family. When you are spending big bucks on a vacation and not having a good time with your travel companions, that can be a recipe for disappointment.

Assuming you get along with would-be travel companions, however, multigenerational travel has a number of advantages.

A lot of families choose multigenerational trips to maximize limited vacation time. My family of four (which includes my husband, our 13-year-old daughter and our 8-year-old son) began traveling with my parents who live across the country for just this reason.

We wanted to see my parents regularly but we didn’t want to spend every holiday break sitting around my childhood home. Instead, we took the family bonding time on the road to more far-flung destinations.

Multigenerational Travel Walt Disney World Olaf
Posing for a picture on a multigenerational trip to Walt Disney World. (Photo by Leslie Harvey for The Points Guy)

With my parents, we’ve now road-tripped Utah’s national parks, lived it up in Las Vegas and Cabo San Lucas and relaxed in the mountains of North Carolina’s High Country.

With my in-laws, who live near us in California, we vacation regularly in Hawaii, Palm Springs and Lake Tahoe. Sometimes aunts, uncles and a cousin or 10 have come along for the fun. Disney parks and resorts have been frequent destinations with many different combinations of family members over the years.

We have made quite a few mistakes along the way, but the memories that my kids have made with their grandparents, aunts, uncles and cousins are priceless. We’ve crossed a number of places off of our travel bucket list in the process and saved some money by sharing a single, larger accommodation.

Plus, my husband and I have been able to explore more on our own thanks to the extra sets of hands that grandparents and other family members have generously provided, especially when our kids were babies and toddlers.

If your family sounds like one that would work well on a multigenerational vacation together, here are the key planning considerations to keep in mind.

Related: the best trips to take with your kids at every age

10 tips for planning the perfect multigenerational trip

Plan and schedule the trip well in advance

(Photo by Nv Phngs Caeng Kml Kul Chay/EyeEm/Getty Images)

Often one of the hardest parts of taking a multigenerational vacation is simply settling on a date. With more people in your traveling party, there will be more schedule conflicts to navigate.

When kids of school age are in the mix, many families choose to plan multigenerational vacations to coincide with school holidays. Of course, these holiday dates are generally when vacation destinations book up extra early. It’s vital to plan in advance if your trips need to take place during peak travel periods.

How early is necessary to kick off the planning process?

If you are planning a family reunion with multiple households, I’d recommend starting the planning well over a year in advance. Some destinations, travel operators and accommodations open their calendars a full year early. You will want to have the basic parameters of your trip set to make those kinds of bookings at the one-year mark.

With smaller multigenerational groups, you may need less lead time to get something on the calendar. When my family invites just grandma and grandpa along for a trip, we’ve sometimes made plans as little as a few months in advance.

Sometimes, the dates thankfully set themselves. My family regularly finds ourselves making travel plans for Thanksgiving week with my husband’s extended family. All of us always have that week off and would prefer to have our turkey someplace different than just at home.

Related: Best trips to take with kids of every age 

Candidly discuss budget and who is paying for what

(Photo by Carol Yepes/Getty Images)

One of the most significant pain points in planning a trip with extended family is the question of money.

Different households will likely have different budgets. Even if all participants are in similar financial situations, not everyone will place the same value on the same parts of the trip. One family unit may prefer to splurge on a fancy resort while another might prefer to stay in modest accommodations to have more cash for activities.

To avoid uncomfortable situations that can spoil a vacation, talk about budget early and often in the planning process. Think about more than just lodging costs when making plans. Flights, rental cars, gas, activities, restaurants, groceries and many other incidentals need to be factored in the budget discussion.

Sometimes on multigenerational trips, one person or household wants to treat their loved ones to part or all of the vacation together. If the trip is going to be gifted to some of the attendees, make those parameters clear up front. Also, make sure your family members are comfortable with the gift. While having someone else pick up the tab is welcomed by many, it can cause embarrassment or discomfort for others.

Related: How to find the best beach house rental

Pick a point person to drive the planning process

Too many cooks in the kitchen spoil the broth, and too many travel planners can spoil a trip.

If you are traveling with a larger group, the family needs to designate one person to serve as the lead travel planner. This family member should track deadlines, send communications, make bookings, and settle up the costs — or at least carefully delegate those specific tasks to others willing and able to help.

Since you are reading this article, chances are pretty good that this point person will be you. Families tend to count on those who are experienced in travel planning to do the heavy lifting on big group trips.

If you don’t want that kind of responsibility or don’t have the time, consider hiring a travel agent to assist you. Someone will still need to serve as the main contact point for the travel agent, but a good agent can likely save the family point person many hours of research and legwork.

Find a destination with something for everyone

Multigenerational Travel on Hawaii Big Island
We vacationed with extended family on Hawaii’s Big Island. (Photo by Leslie Harvey for The Points Guy)

Choosing a destination for a multigenerational trip requires a lot of time and research. There are many destinations that ultimately work well, so don’t stress the perfect place too much. The key is making sure the destination has something to offer all ages and traveler types in your group.

What kind of destinations work well for multigenerational travel?

Beach vacations are an obvious choice and what my family has settled on most over the years. National parks also work well, as they combine adventure with history and learning. Cruises are often a great fit because the entertainment and activities aboard caters to all ages. (But be sure that no one in the family has issues with motion sickness.)

Disney destinations are, of course, incredibly popular for multigenerational traveling groups. We’ve been to both Disneyland and Walt Disney World with grandparents, but a week of walking 20,000+ steps a day in a theme park may not be doable for everyone.

If the draw of Mickey is nevertheless powerful, consider Disney’s non-theme park options like the Aulani Resort in Hawaii, the Disney resorts in Vero Beach, Florida or Hilton Head, South Carolina, or Disney Cruise Line.

Disney Aulani in Hawaii. (Photo by Summer Hull / The Points Guy)

Don’t be afraid to think outside the box when settling on a destination.

When I took my parents and my young kids to Las Vegas, a lot of friends thought it was an odd choice — but we had a fantastic time. The destination has many family-friendly shows and activities that are ideal for kids and grandparents alike.

In some circumstances, some members of the family may already have chosen a destination and then invite other family members along. If you are on the receiving end of this kind of invitation, consider carefully whether the destination will work for your immediate family. Don’t feel bulldozed into a vacation that isn’t right for you. If it doesn’t work, perhaps offer to plan the next extended family trip.

Pick a destination everyone can travel to

A destination also needs to be accessible. If family members are coming from different places, make sure they can get there with reasonable ease. You don’t always have to meet in the middle or agree to equivalent travel times, but make sure that a destination isn’t out of reach due to excessive travel time or cost.

When I planned a large family reunion a few years ago, we held it on Alabama’s Gulf Coast beaches in large part because the destination was accessible for everyone.

It was within driving distance of family members who lived in Southern states, and it was also near two different airports in Mobile, Alabama, and Pensacola, Florida, giving farther-flung attendees multiple airline choices. (A bonus was that one of those airports is served by Southwest Airlines. Most of the flying family members live in Southwest focus cities and were able to use Rapid Rewards points to fly to the reunion on the cheap.)

Consider mobility and other limitations

A multigenerational national park adventure at Bryce Canyon National Park. (Photo by Leslie Harvey for The Points Guy)

With a multigenerational group, there are potentially more limitations in the travel party to consider. Talk about these concerns before you get too far in the planning process.

For example, are there any members of the family with mobility limitations you need to accommodate in choosing appropriate lodging and activities? Even active grandparents (or young toddlers) might have mobility concerns like not being able to navigate too many stairs in a multi-level condominium daily.

Is there is a baby or toddler in your travel group? Nap time and early bedtimes are important considerations to plan around. Destinations with a lot of nightlife might not be the best fit if someone always has to go back to the hotel or vacation rental early every evening to put a little one to bed.

Decide on lodging

Once you’ve settled on a date and destination, the next major step is booking accommodations.

Ideally, you should look at the types of lodging that are available when you are comparing several destinations. At the very least, you need to make sure all the destinations have options that would work for your traveling group and that there is availability for your dates. The next step is drilling down to a specific booking in a specific location.

There is no one-size-fits-all when it comes to lodging on a multigenerational trip.

What the best lodging is for a group will likely depend a lot on the destination. In places where vacation rentals are plentiful, renting a house or other large unit to share on a site like VRBO or Airbnb is often the best option. Family members can all have their own rooms and bathrooms but can share common spaces and spend time together.

Often a vacation rental is more economical when split several ways as well.

Ski rental house. (Photo by Summer Hull/The Points Guy)

Related: 13 mistakes to avoid on your next vacation home rental

A house or condo rental may not work in every destination, though. Some families also may want the amenities of a large resort and not want the isolation or lack of services of a home rental.

In some destinations, vacation rentals simply may not be practical for what you want to do and see. For example, when my family traveled with my parents to Zion National Park, a vacation rental would have put us too far from the action. Instead, we booked adjacent hotel rooms at the historic lodge within the park. This gave us easy access to the Zion shuttle, which made the destination more navigable for my parents.

Whatever you book, pay special attention to cancellation policies.

With a larger group, the possibility that someone may not be able to come on a trip due to an injury, illness or other emergency is greater. Flexible bookings are always smart when a lot of money is on the line. Before you book anything shared that is non-cancelable, make sure everyone in the traveling group agrees how the costs will be allocated if someone in the group ultimately cannot attend.

Set clear boundaries on expected babysitting by extended family members

Multigenerational Trip to Disney World
We went to Disney’s Hollywood Studios with my aunt and kids. (Photo by Leslie Harvey for The Points Guy)

One of the reasons many parents with young children appreciate multigenerational travel is that it often comes with built-in babysitters. My husband and I have been on the receiving end of some extraordinary babysitting generosity on our multigenerational trips over the years.

But chances are good that grandparents or other extended family members aren’t traveling to a far-flung destination just to sit in a hotel room and care for someone else’s little ones, even if they love the kids dearly.

If you are likely to be the babysitter on a multigenerational trip, let your family members know exactly how much you are willing to pitch in to help with the kids.

Offering up a single date night or taking a younger sibling for a few hours during the day so parents can enjoy an activity with an older one is reasonable and likely to be appreciated. But don’t let the default be that you are on duty the entire trip. Likewise, if you are the recipient of babysitting help (like I have been in recent years), don’t just take advantage and perhaps also consider doing something extra special for family members who help.

Related: Skip-gen travel trends: the 8 best grandparent-grandchild getaways

Divide the work — or outsource it

Ideally, vacations should be all about R&R, but the reality is that many still require significant work while you are on them. Vacation rentals especially can come with a lot of extra chores, including cooking and cleaning to do daily just like at home.

Don’t expect others to do that work or let one person inadvertently do more than their fair share by default. Assign tasks in advance and choose what you are able to (and want to) outsource.

The last few years, my daughter has always made a meal calendar for our extended family trips to Lake Tahoe and Palm Springs. She assigns each family to cook dinner on one night of a weeklong trip in our vacation rental.

Dinner time in the home rental. (Photo by Summer Hull/The Points Guy)

On the other nights, we eat out or grab takeout. Sharing the load and having those expectations set before our trip has worked out well to avoid anyone being too overburdened — and we all get several nights off on vacation thanks to her pre-planning.

Don’t plan to do everything together and avoid micromanaging others

With a multigenerational travel group, there will be different travel interests and paces. While it’s fun to do some activities together during the day, too much togetherness can sometimes create conflict.

Don’t try to over-schedule everyone or micromanage every minute of the trip. Leave some free time for individuals or smaller family groups to pursue their own interests or just have downtime.

As the travel planner in my family, I’ve found what often works best is to inform everyone of their activity options but not to schedule everything. I often put together a list of local activities at the destination. Family members can peruse the list and form smaller groups to participate in various pursuits based on what interests each person most. I plan a couple of big group events (like a dinner at a local restaurant) but let the rest of the schedule work itself out as we go.

Related: Why a ski trip may be the best extended-family vacation 

Bottom line

Although they require a little more planning, multigenerational vacations can be an extremely rewarding travel option. Multigenerational trips offer the chance to reunite family members, share the work and cost of travel, and explore new places.

For more multigenerational travel tips, see these related articles:

Featured image by Morsa Images/Getty Images.

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