Multi-Generational Travel: How to Make Unforgettable Memories With the Whole Family

Thinking about a family getaway with kids, parents, and grandparents? Here’s how to make multi-generational travel fun, affordable, and unforgettable—from someone who’s done it.

Why Multi-Generational Travel Is Our Favorite Kind of Adventure

Have you ever imagined enjoying in Italy with your grandkids, or surfing in Mexico while your kids and grandkids cheer you on from the beach? That’s the magic of multi-generational travel—and let me tell you, it’s one of the most rewarding ways to see the world.

As full-time travelers who also happen to be parents and grandparents, we’ve experienced firsthand how incredible (and chaotic!) it can be to bring three generations together for one trip. Whether it’s traveling through Europe with our daughters or exploring a tropical paradise with our grandkids, these trips have become some of our favorite travel memories ever.

But let’s be honest—traveling with your whole crew isn’t always easy. From budget planning to choosing the right destination, there are a lot of moving parts. That’s why we’re sharing all our top tips, favorite destinations, and budget-friendly hacks to help you make multi-generational travel not just possible—but magical.

What Is Multi-Generational Travel?

In a nutshell, multi-generational travel is when three or more generations travel together—think grandparents, parents, and kids (and sometimes even great-grandparents or cousins). These trips are perfect for:

• Celebrating milestone birthdays or anniversaries
• Spending quality time as a family
• Introducing younger generations to new cultures
• Making memories that truly last a lifetime

It’s not just a trend—it’s a growing movement. More families are choosing experiences over stuff, and multi-generational travel is the ultimate shared adventure.

Why We Love Multi-Generational Travel (and You Will Too)

You know that warm, fuzzy feeling you get when your whole family is in one place, laughing around a dinner table or cheering each other on during a game night? Now imagine that—but in a villa in Hawaii or on a the beach in Mexico That’s the magic of multi-generational travel. It’s not just a vacation—it’s an experience that brings generations together in ways that daily life often doesn’t allow.

Here’s why we’re such big fans:

1. Quality Time You Can’t Get at Home

Let’s be real—between soccer practice, work meetings, and school pick-ups, it can feel nearly impossible to slow down and connect. Multi-generational trips hit the pause button. They give you real, uninterrupted time together, where the biggest decision is: pool or beach?

There’s something deeply meaningful about waking up in the same house, making breakfast together, and spending the day adventuring as a team. These moments are the glue that holds families together.

2. Shared Experiences = Stronger Bonds

We’ve found that travel brings out the best in people—and sometimes the funniest sides, too. You’ll see your kids try local street food, your grandkids giggle as they attempt new words in a foreign language, and your partner channel their inner tour guide as they lead the way through cobblestone streets.

These shared experiences build bonds that are hard to replicate back home. When everyone’s learning something new or getting out of their comfort zone, magic happens.

And the best part? You’ll have stories to laugh about for years. (“Remember when Grandpa tried surfing?” Yes, yes we do.)

3. Built-in Support System

Traveling with family means you don’t have to do it all alone. Grandparents can watch the kids for a date night. Grown kids can help with logistics. Older kids can keep the little ones entertained on long travel days. Everyone pitches in.

And if someone needs a break? That’s okay too. With more adults around, you can tag-team and make sure everyone gets rest and relaxation. Our favorite part of taking a big family trip is sending the parents off so we can have time with all the grandkids in one place.

4. Kids Learn from Their Elders—and Vice Versa

Some of our favorite moments have been watching our grandkids soak up stories from their aunts and uncles, or our adult children learning recipes and traditions in a new country together with us.

There’s this beautiful intergenerational exchange that happens naturally on trips. Travel becomes a classroom, and everyone has something to teach and something to learn.

5. It Turns “Someday” Into “Right Now”

We all say we want to spend more time with family. But if we’re honest, someday often turns into never. That’s why we’re so passionate about encouraging multi-generational travel.

You don’t have to wait for a wedding, retirement, or “perfect timing.” The time is now. And whether it’s a weekend road trip or a month-long adventure, it’s always worth it.

Planning a Multi-Generational Trip: 7 Tips for Stress-Free Travel

Planning a trip for multiple generations can feel a little like herding cats—adorable cats, but still. With different interests, energy levels, and schedules, it’s easy to feel overwhelmed. But after traveling with our kids and grandkids, we’ve learned a few things to help keep the chaos to a minimum and the joy to a maximum.

Here are our go-to tips for planning a smooth, fun, and memorable multi-generational trip:

1. Start Planning Early

Multi-generational travel requires a little more lead time, especially if you’re coordinating school breaks, time off work, or multiple flight schedules. We recommend starting the planning process at least 4-6 months in advance, if not more for international trips or peak travel seasons.

Give everyone a chance to weigh in on dates and destinations early—group chats or shared Google Docs are lifesavers!

2. Pick a Destination with Something for Everyone

Look for places that offer something for everyone—beaches, walkable towns, kid-friendly attractions, and relaxing options for older family members. Some of our favorite multi-generational spots:

• Bali – affordable luxury, gorgeous villas, and culture for all ages
• Portugal – charming cities, great food, and stroller-friendly cobblestone streets
• Costa Rica – wildlife, adventure, and family-sized Airbnbs
• Cruises – hear us out: everything from kids camp to family-friendly entertainments to all the food you can possibly eat is included

Pro Tip: Avoid places with long travel times or extreme weather if you’re traveling with older adults or very young kids.

3. Book Family-Friendly Accommodations

Skip the hotel rooms and go for a villa or Airbnb with a kitchen and common areas. You’ll save money on meals and enjoy way more together time. There’s something incredibly special about having everyone sleeping under one roof. Waking up to the sound of kids laughing in the kitchen, sharing morning snuggles with your grandkids on the patio, and ending the day with a late-night game or storytime—it all creates this cozy, family-camp kind of vibe that you just can’t get when everyone’s in separate hotel rooms. Plus, staying in one place cuts down on transportation costs and makes coordinating activities much easier. Look for:

• Multiple bedrooms and bathrooms
• A central location
• A pool or yard for kids to play

We once booked a 3-bedroom villa in Bali for under $900/month—and it came with a private pool! We put together a list of the top ten tips for finding the perfect Airbnb for your next vacation HERE.

4. Build In Downtime

This one’s huge. When you’re traveling with a range of ages, not every minute needs to be scheduled. In fact, we highly recommend leaving plenty of white space in the itinerary.

Nap breaks, beach days, long lunches, or afternoons lounging by the pool give everyone time to recharge—and help avoid meltdowns (from kids and adults!).

We try to alternate big sightseeing days with low-key ones and always remind ourselves: it’s okay to skip something if it means keeping the peace.

5. Be Flexible (and Patient!)

No trip goes exactly according to plan, especially with a large group. Someone might forget their passport, get sick, or just be hangry (been there). The key is to stay flexible, keep your sense of humor, and go with the flow.

Sometimes the best memories come from the unexpected moments—like the time we got lost on a family hike in Italy and ended up discovering the cutest little café for lunch.

Roll with the punches, and keep the bigger picture in mind: you’re making lifelong memories together.

6. Assign Roles and Share Responsibilities

Don’t take it all on yourself! Multi-generational travel is a team effort. Assign roles based on people’s strengths:

• One person handles booking transportation
• Another plans meals or makes dinner reservations
• Someone else keeps track of kids’ needs or medical supplies

Even teens can help—they’re often great at navigating or handling translation apps.

Sharing the load means less stress and more fun for everyone.

7. Prioritize Communication

This might be the most important tip of all. Make sure everyone is on the same page about:

• Budget expectations
• Activity levels and accessibility
• Food preferences or allergies
• Daily plans and free time

We’ve found that regular check-ins (even quick morning huddles) help keep the group organized and minimize confusion. And if you have a big crew? Consider using a group chat or a shared itinerary app to keep everyone in the loop.

Budget-Friendly Ideas for Multi-Generational Trips

We get it—traveling with a whole crew sounds expensive. But it doesn’t have to be.

Here’s how we save:

• Travel in the off-season for cheaper flights and lodging
• Use travel deal alerts from JetsetClub.co to book flights
• Book longer stays to get discounted Airbnb rates
• Split costs between family members
• Cook meals at your rental instead of eating out every day
• Find a location that’s driving distance for at least the majority of your family
• Use public transportation instead of rental cars when possible

With a little creativity, multi-generational travel can actually be more affordable than taking separate trips.

Our Favorite Multi-Generational Travel Moments

There were the times we took our wakeboard boat and a houseboat on Lake Powell, and our kids took turns being “captain” while my husband sang sea shanties. Or the time we made homemade pizza with three generations gathered around one tiny kitchen table at a beach house in California. Those are the kinds of memories we’ll never forget.

Travel has given our family the greatest gift: time together in a world that often pulls us apart.

Final Thoughts: Yes, You Can Travel the World as a Family

Multi-generational travel isn’t just doable—it’s deeply meaningful. It’s about creating experiences that span generations, cultures, and time zones. You don’t have to wait for a “perfect moment” or a big budget.

If we can do it, so can you.

Let’s Chat!

Have you ever taken a multi-generational trip? Or are you planning one soon? Drop your questions or share your favorite travel memory in the comments—we’d love to hear from you!

And if you’re looking for travel deals to get the whole family somewhere amazing, check out our travel deal site at JetsetClub.co—we’ll help you find the perfect flight for less.

Related Posts You Might Like:

• How to Find the Best Airbnbs While Traveling
• The Ultimate Bali Travel Guide
• Traveling Internationally Over Thanksgiving: Why It’s the Perfect Time

Travel isn’t just about places—it’s about people, experiences, and making memories. Hi! We are Shayne and Shelly Peterson. As empty nesters, we’ve found new ways to connect with the world (and each other) through travel. Follow our journey at JetSetPetersons.com and let’s explore together! 

At Jet Set Petersons, we occasionally collaborate with brands, companies, and tourism boards to bring you content that aligns with our love for travel. Some of the posts on this website may include sponsored content, affiliate links, or gifted experiences.

We only partner with brands that we genuinely love and believe will bring value to our readers. While we may receive compensation in the form of payment, free stays, or complimentary products, all opinions expressed are our own. Honesty and transparency are at the core of what we do, and we would never recommend anything we wouldn’t personally use or enjoy.