Multigenerational Vacations: 6 Steps For Planning a Trip Together

AdobeStock_92278099-300x212There are few experiences more transformational than travel. Visiting new places, whether near or far, has a way of opening our hearts and minds.

And when we travel with people we love, there is the added benefit of being able to share those memorable experiences. From a simple weekend road trip to a month-long journey exploring another country, travel can change your life and your relationships for the better.

Two of the things people missed most during the first two years of Covid were spending time with family and travel. Knowing this, it’s not that surprising that as Covid-related travel restrictions lifted more and more people started booking trips that included extended family. Multigenerational travel was a growing trend prior to Covid, and it has become even more popular now that—hopefully—the worst of the pandemic is over.

Multigenerational Travel — A World of Possibilities

Traveling with family can be:

  • a mother/daughter trip;
  • a grown child and their partner with parents;
  • three generations of parents, kids, and grandparents; or
  • a full-on family reunion including all of the above plus aunts and uncles and cousins. 

Many young adults are enjoying additional travel experiences with their parents before they start their own families. These trips create a whole new relationship dynamic that provides a chance to bond in ways that weren’t possible when the kids were young. These kinds of trips also give older parents the chance to see places and do things that they might not attempt on their own. Traveling can be daunting as we age, so it can be a big comfort and confidence builder to have adult children along for the adventure. 


A trip that includes three generations is a great opportunity for creating treasured grandparent/grandchild memories that will last a lifetime. This can also be a great solution if you’re short on vacation time. Instead of having to choose between a vacation destination and a trip to visit the grandparents (or cutting each trip short), you can combine the two into an event that includes everyone. 

Another trend that’s growing in popularity is ancestry travel. As it’s become easier and less expensive to explore family genealogy through DNA testing and research sites, people have become increasingly interested in traveling to places that can help them rediscover their roots. And what better way to make such a trip more meaningful than to travel with extended family and multiple generations? Ancestry travel often includes trips to distant destinations tied to a family’s origins many generations back, but it can also include domestic trips. For example, a family might travel to the city that became home for past generations of immigrant ancestors.

It’s nice to have a destination that holds some personal meaning to one or more family members, but in the end the important thing is just to spend time together. Many multigenerational trips are to places like Disney and other theme parks, all-inclusive resorts, and even cruises. 

Planning the Perfect Multigenerational Trip — Pay Attention to the Details 

1. Planning: Start Early and Centralize Communications

Every great event starts with a great plan, and when it comes to travel, your best bet is to plan way ahead. Most trips require a decent amount of advance planning, but when you’re coordinating for a larger group (who come from different households), it’s not unreasonable to get started a full year ahead of your intended departure date. 

In addition to starting early, it’s also smart to put one person in charge of overall planning and communication. This person doesn’t have to be responsible for making all the decisions, but they will help create order out of chaos by keeping track of details, schedules, itineraries, booking confirmations, budgets, and so forth. This person will also be the communications hub for your whole party—the person who keeps everyone informed of what’s happening when, and also makes sure everyone is doing what they need to do (like providing information, making budget contributions, etc.). 

2. Budget: Be Clear Right Up Front 

Money is almost always a tricky subject, especially with family. For best results, always be candid about the budgeting process. This means having frank conversations about who pays for what, how much each contributor can afford, and what the spending priorities are for the group. 

While flights, lodging, and special activities (like theme parks) will make up the lion’s share of the expenses, don’t overlook incidentals like car rentals or Uber/Lyft fares, dining out, souvenirs, and even tips for porters and valet parking. Those small amounts can add up fast.

3. Destination: Consider Proximity, Accessibility, and Activities

out-of-state-property-300x188It’s often said that the journey is more important than the destination, but when it comes to multigenerational travel, you need to pick your destination carefully. You want to pick a place that is roughly equidistant from each member of your party. In other words, you don’t want to pick a location that is only a half-hour drive for some folks, but a six-hour flight for others. 

You also want to consider general accessibility, especially if you have travelers in your group who are older, or have mobility limitations. If, for example, you’re heading to a big theme park, make sure to have a conversation about how much walking everyone is prepared to do in the course of a day. And if someone has concerns about being on their feet all day, maybe check into the availability of wheelchairs or other assistance. Or maybe choose a different destination. 

Finally, take care to choose a destination that offers activities to appeal to all the different members of your group. This can be a little tricky if you have a wide range of ages (toddlers to grandparents, for example), or even just a wide array of interests (shopping vs hiking vs hanging out on the beach). No one place will be perfect for everyone, but you can always find a location that has a little something for everyone. 

4. Lodging: Think About Space, Privacy, and Amenities

From quaint bed-and-breakfast inns to all-inclusive resorts to unique Airbnb accommodations, there are so many different types of lodgings to choose from. When traveling with a group, it’s best to get clear input from everyone about what they’d like in terms of amenities (a pool, room service, cleaning service, on-site dining, etc.). It’s also important to establish how much privacy everyone needs. For some families, having everyone stay in one house with multiple bedrooms is the way to go. For others, it’s best to have a little more privacy and space. 

5. Expectations: Don’t Make Assumptions About Cooking, Cleaning, or Babysitting

Falling into old patterns is one of the biggest potential pitfalls of traveling with family and friends. Grown children assume that their parents would love nothing more than to take the grandkids for the day (or the evening). Or certain family members might assume that the folks who do most of the cooking and cleaning at home will automatically handle those tasks during the vacation as well. Don’t fall into that trap! Remember that a trip is meant to be a vacation for everyone; and no one signed up for on-the-road chores or childcare duties. Set expectations up front. Make sure you know what each person is willing (and unwilling) to do. And if there are tasks that no one volunteers for, consider finding another way to cover those items, like ordering out, hiring cleaning staff, or setting up a shared schedule for babysitting. 

6. Itinerary: Make Plans, But Go with the Flow!

Last, but certainly not least, one of the most challenging aspects of traveling with any group is coordinating everyone around the various activities you have planned. If you’re the person in charge of organizing events and sightseeing, you can start to feel like the proverbial herder of cats in no time at all. To save yourself a lot of stress, don’t try to schedule every minute of every day with a fully packed itinerary. Instead, pick out a handful of key activities you’d like to do as a family or sights you’d like to visit together, and then leave the rest of the schedule open. It’s also perfectly acceptable to offer up a bunch of different activity choices that are optional, and let your travel companions pick and choose what they’d like to do. 

At the end of the day, multigenerational travel is about spending time with people you love—sharing new experiences, making memories, and maybe even learning a bit more about each other. There is no one right way to do this, and if you can learn to go with the flow, you may find that the perfect way finds you. 

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