How to Plan a Multigenerational Trip Everyone Will Actually Enjoy

I love traveling with my family. I also know from experience that traveling with your family and planning travel for your family are two very different things.

The picture in your head when you first start planning is always lovely. Everyone exploring a new place together, grandparents experiencing something with their grandchildren, long dinners where we talk about the day, and those great family photos that become more meaningful as the years go by.

What you don't picture quite as clearly is standing in a hotel lobby wondering how the people who were told we were leaving at 9:00 are still upstairs at 9:17.

We've traveled together enough over the years that I've learned to expect both versions.

Our trips include different generations, personalities, interests and energy levels. We have people who could spend hours exploring a historical site and others who would be perfectly content to give it a respectful 45 minutes and move along. Some of us want to see everything. Some want time to shop. Some are already thinking about dinner while we're eating lunch. And there is always somebody who could use a little more downtime than I originally planned.

It took me a few trips to realize that none of this is a problem I need to solve. It's simply information I need to plan around.

That's probably the biggest lesson multigenerational travel has taught me.

I Plan for the People Now, Not Just the Place

When I first started planning our trips, I spent most of my time researching the destination. What should we see? Where should we eat? What are the things we absolutely shouldn't miss?

I still do all of that—I genuinely enjoy it—but now there's another layer to my planning.

I think about us.

Who is actually going on this trip? What is each person going to be excited about? Who will happily walk all day and who won't? Who needs a little downtime? What will the teenagers enjoy? What will the adults enjoy? What can we experience together that won't feel as though half the family is simply tolerating it for the other half?

Because that's the trap with family travel. You can create an objectively fantastic itinerary that is completely wrong for the people traveling on it. We've learned that everyone doesn't have to love everything. They just need enough things they love.

One of the things I try to do now is make sure every person has something on the trip that feels like theirs. It doesn't necessarily need to be a full day or some expensive excursion. It might be a particular historical site, a restaurant, a shopping area, a show, a beach afternoon or something oddly specific that one person discovered while researching the destination.

I actually love seeing everyone else's interests make their way into our trips. We've all ended up doing things we probably wouldn't have chosen ourselves, and sometimes those experiences become favorites.

But there's a difference between asking someone to spend two hours doing something because another family member loves it and asking them to spend five days doing someone else's vacation.

We've gotten much better at recognizing that.

Everything Takes Longer Than I Think It Will

This is one of those lessons I apparently needed to learn more than once. Moving a group of people takes time.

Getting everyone out of multiple hotel rooms takes time. Getting through breakfast takes time. Someone has to go back upstairs for something. Someone needs coffee. Someone needs a bathroom. Someone thought we said 9:30 when everyone else heard 9:00.

Then there is the actual process of getting from one place to another.

I used to build itineraries based on how long Google told me something would take. If the museum was a 20-minute walk from the hotel, great. Twenty minutes. That calculation is adorable to me now.

A 20-minute walk with a multigenerational group is not necessarily a 20-minute walk. There are traffic lights, interesting shops, slower walkers, faster walkers who have to stop and wait, somebody taking a picture and somebody asking whether we're almost there.

I've learned to put space between things. More than I think we'll need. The result has actually been better trips because we're not constantly looking at the clock and feeling as though we're behind. If we arrive early, wonderful. We get coffee. We look around. We sit for a few minutes.

And if it takes us longer than expected—which it usually does—we're fine.

I Have Also Made Peace with the Uber Budget

I am still guilty of looking at a map before a trip and saying, “Oh, we can walk that.”

Sometimes we can. Sometimes we even do. But I have become much more realistic about the difference between a perfectly reasonable walk at 10:00 in the morning and that exact same walk at 5:00 after we've been sightseeing all day. There comes a point when saving the Uber fare is simply not worth it.

If someone is tired, someone's feet hurt, we're running behind, it's hot, it's cold, or everyone would simply arrive at dinner happier if we got in a car, we get in the car.

With a bigger group, that sometimes means multiple cars, which is another expense I didn't always appreciate when I first started planning family travel.

Now I account for it.

I've realized that transportation isn't just about moving people between places. Sometimes you're buying back energy, time and patience, and all three are pretty valuable on a family vacation.

We Don't Have to Be Together Every Minute

This was another evolution for us. There is a natural feeling when you're taking a family trip that everyone should do everything together. After all, isn't that the whole point?

Except sometimes half the group wants to do one thing and the other half really doesn't. We've learned to split up.

It doesn't happen constantly, and some of our favorite experiences are absolutely the ones we share as a whole family. But if a few people want to spend an afternoon at a museum while someone else wants to shop or go back to the hotel for a while, that isn't a failed family vacation.

Sometimes it's exactly what everyone needs. Then we meet back up for dinner and everyone has something different to talk about.

The older our kids have gotten, the more valuable this has become. The trip can still have a shared rhythm without requiring everyone to spend every waking minute in a single group.

Honestly, I think we enjoy our time together more because of it.

I Still Love an Itinerary

Nobody who knows me is going to believe I've become a “let's just show up and see what happens” traveler. I have not.

I like knowing what we're doing. I like researching restaurants. I like having reservations. I want to know when things open, how far apart they are and whether we're going to discover after arriving that the one thing we really wanted to see requires tickets purchased three months ago.

Planning gives us options. What has changed is the way I structure the day.

Instead of filling every available space, I build around a few anchors. Maybe we have a 10:30 tour and a 7:30 dinner reservation. Those are fixed. The rest of the day has a plan, but it also has room. That room is where real travel tends to happen.

We find a shop we want to explore. Lunch takes longer because we're enjoying ourselves. Someone wants to sit down for a while. We stumble across something I never found in all my research.

Or—and this is an important one—we decide we're tired and go back to the hotel. Years ago, that would have bothered me. We came all this way! There are things to see! Now I understand that there is very little value in seeing one more thing if everyone is too exhausted to enjoy it.

You Learn to Recognize When You're Losing the Group

There is a point on a busy travel day when I can tell we're done. Nobody necessarily announces it. You just start seeing the signs. 

The pace slows. People stop looking around as much. The enthusiasm level drops. Someone asks what time dinner is for the third time. A teenager who was participating in conversation an hour ago has largely stopped communicating.

That's when I've learned not to push. Maybe we stop somewhere for a drink or something to eat. Maybe we head back to the hotel for a couple of hours. Maybe the activity I had penciled in for late afternoon quietly disappears from the itinerary. That's okay.

I'd rather have everyone rested and enjoying the evening than proudly announce that we successfully completed 100 percent of the day's scheduled attractions while six people glare at me over dinner.

The itinerary is supposed to help us have a great trip. Completing the itinerary is not the trip.

That sounds obvious, but for those of us who really enjoy planning, it can take a little practice.

Food Has Become Part of the Strategy

Meals are a big part of travel for us, and I've learned that they need the same balance as everything else.

We might have a restaurant we've been looking forward to for months, and I'll absolutely plan around it. But every meal can't require the entire group to get dressed, arrive at a specific time and commit to a two-hour experience.

Sometimes we need the special dinner. Sometimes we need sandwiches.

Food halls and markets can be especially great with a mixed group because everyone gets to make their own choice. Nobody has to negotiate one restaurant that somehow satisfies every appetite and preference at the table.

I've also learned not to wait too long to feed people. There is a very narrow window between “We should probably start thinking about lunch” and “Everyone has lost the ability to make a rational decision.”

We try to stay on the correct side of that window.

One Question Has Changed the Way I Plan

Before a family trip, I want to know one thing from everyone:

What is something you really want to do while we're there?

I don't need everyone to research the destination. They don't need to study an itinerary or send me a list of 20 attractions. I just want to know what would make the trip feel special to them. The answers give me the pieces I need.

Then I can start fitting them together—balancing interests, geography, energy, reservations and the amount of time we realistically have. That's what I think a custom family itinerary should be.

It shouldn't simply tell you what there is to do in a destination. Google can do that. It should reflect the people who are actually going.

Our Trips Aren't Perfect. They're Ours.

We've missed things. We've changed plans. We've spent more on transportation than I intended. We've had afternoons where everyone needed a reset. We've eaten somewhere that looked much better online. We've had teenagers who weren't remotely interested in something I was sure they would love.

We've also laughed until we cried. We've watched our kids discover places and experiences that surprised them. We've shared meals we'll talk about for years. We've had grandparents and grandchildren experience things together that simply couldn't have happened at home.

And we've accumulated family stories. Some are about the incredible places we've visited. Some are about things that went completely wrong. Both kinds get retold.

That's really why multigenerational travel matters so much to me. There will come a time when getting all of these people together for a trip becomes harder. Kids grow up. Schedules change. Families expand. Life moves quickly.

Right now, we have opportunities to go. So, we go.

I don't need everyone to love every museum, every restaurant or every item on my itinerary. I don't need us to spend every minute together. And I've finally stopped believing that changing the plan means I didn't plan well enough.

What I want is for each person to find something in the journey that belongs to them, while all of us come home with stories that belong to us. That is how our family has learned to travel together.

And at The Curated Mile, it's how I approach multigenerational travel for other families, too. Before I think about filling days with attractions, I want to understand the people taking the trip: what excites them, what doesn't, how they like to travel, where they may need a little breathing room and what they hope they'll remember when it's over.

Because a great family itinerary isn't the one that gets everyone everywhere. It's the one that gets your family right. 

Planning a journey for several generations?
The Curated Mile creates thoughtful, personalized travel experiences designed around the people taking the journey—not just the destination. Explore our Journey Collections to discover how we approach multigenerational travel.