The Best Family Trips by Age: When and Where to Travel With Kids

We’ve been lucky enough to take a lot of incredible trips as a family, but a few truly stand out. These are the kind of trips that all four of us, kids and parents alike, would happily do again in a heartbeat.

To put this list together, I asked each of the kids to name their top five favorite places we’ve traveled. I compared their answers to mine and my husband’s…and that’s where things got interesting.

There were some real surprises. For instance, I fully expected Greece to make our top five, but it didn’t appear on either kid’s list. On the flip side, Ireland made a strong impression – even though we only spent four nights there.

What this exercise really reinforced for me is that timing matters. Kids can be too young, or even too old, to fully appreciate certain destinations with their family. When planning family travel, especially if your goal is to make everyone happy, it’s worth considering not just where you go, but when you go.

Below are our top five family vacations so far, along with how old the kids were on each trip.

Japan leaves a lasting impression on just about everyone, and our family was no exception.

I’m especially glad we waited until the kids were a little older for this trip. At 17 and 14, they could truly appreciate the culture, history, and way of life, rather than just the highlights.

We split our time between Tokyo and Kyoto, which worked out beautifully, giving us a perfect balance of modern energy and traditional charm. One unexpected highlight was Tokyo Disney Sea, which I highly recommend if you’re visiting the area, even for older kids and teens.  We stayed in Tokyo at Mimaru Suites Shinjuku and in Kyoto at the Hilton DoubleTree Higashiama. I would recommend both hotels to anyone.

What can I say? It’s Italy. We spent two weeks exploring Venice, Cinque Terre, Rome, and the Amalfi Coast.  Dividing our time between larger cities and smaller coastal towns helped break up the trip and kept it from feeling overwhelming. It gave the kids a little taste of everything Italy has to offer – history, food, beaches, and iconic sights- and made the itinerary feel well-paced for family travel.

This is the only destination on our list that’s specific to a resort, and honestly, I don’t think it would have made the top five if it weren’t for Hotel Xcaret itself.

The all-inclusive experience exceeded our expectations, especially with the sheer number of excursions and activities included. Because so much was built into the stay, we were able to do things we might not have otherwise prioritized.

During this trip, we visited the Tulum Ruins, explored Xcaret Eco Park, went cave swimming, zip-lined, and packed in far more adventure than we usually would on a beach vacation… and we did this all without feeling rushed.

I had to leave a spot on this list for Maui. This is not because we haven’t loved the other Hawaiian Islands, but because Maui is the one we return to again and again.

We’ve traveled to several of the Hawaiian Islands over the years, especially when the kids were younger, and every trip has been fantastic in its own way. Hawaii is generally an incredible destination for family travel. But Maui has become our constant, still working for us as our kids grow and our travel style evolves.

One of the perks of living in California is that Hawaii is relatively easy and affordable to get to, which has allowed us to return often. Over time, we’ve found our rhythm on Maui, particularly in the Napili Bay area, where we almost always rent a condo. Having extra space, a kitchen, and a walkable beach nearby has made Maui feel both comfortable and effortless as a family destination.

Napili Bay has consistently been our favorite spot. The calm water is perfect for younger kids, while the snorkeling just offshore keeps older kids and teens just as happy. It’s relaxed, low-key, and ideal for slower mornings, beach-filled days, and evenings that don’t require much more than a sunset and dinner at home.  If we are not renting a condo, we love splurging on a stay at the Napili Kai, our favorite resort on the island.

What makes Maui stand out is how well it adapts to different stages of family life. When the kids were little, it was all about easy beach days. As they’ve grown, it’s become about snorkeling, hiking, and exploring more of the island without ever losing that familiar, easygoing feel.

Some trips don’t make the favorites list – at least not right away.

One of our most meaningful family trips was a road trip across the United States, stopping at Yellowstone National Park, Mount Rushmore, the Colorado Rockies, the Grand Canyon, Monument Valley, and Arches National Park.

We loved this trip deeply. The wide-open roads, the changing landscapes, and the long days together all felt like one of those trips that would stay with us for a long time. The kids, who were 13 and 10 at the time, didn’t list it as their favorite when I asked. And that’s okay.

Some trips don’t register immediately. They’re not about instant excitement or clear highlights. They’re about time, long conversations in the car, crazy stories, early mornings, and quiet moments that don’t feel significant until years later.

I have a feeling this road trip will be one of those memories. The kind that grows more meaningful with distance. The kind they’ll look back on someday and realize how much we saw, how much we shared, and how much it shaped the way they remember traveling together as a family.

And maybe that’s the point, not every favorite has to be immediate.

Putting this list together was a good reminder that the best family trips aren’t always about checking off bucket-list destinations.  They’re about timing, flexibility, and choosing places that meet your family where they are in that season of life.

Some destinations surprised us. Others didn’t make the list at all, even though they were wonderful trips. And a few places, like Maui, earned their spot simply because they worked again and again, through so many different ages and stages.

If there’s one takeaway from our top five family trips, it’s this: travel doesn’t have to be once-in-a-lifetime to be meaningful. Sometimes, returning to a place you love and experiencing it differently as your kids grow is what makes it truly unforgettable.