PLANNING A VACATION WITH KIDS & GRANDPARENTS: WHAT EVERY FAMILY SHOULD KNOW BEFORE BOOKING

Planning a vacation with kids and grandparents is unlike any other family trip.

You're not just coordinating flights and accommodations. You're bringing together different generations, travel styles, budgets, and expectations, all with the hope of creating a vacation everyone will enjoy.

When it all comes together, those trips become some of the most meaningful family memories you'll ever make.

I know that because I grew up travelling with my grandparents. One of my favourite memories is from a Disneyland vacation with my grandma and grandpa. On our last day, we all stopped for ice cream before heading home. My grandpa ordered a chocolate-covered frozen banana, took one big bite... and chipped his tooth. We laughed so hard, and joked that at least it happened on the last day of the trip.

Years later, our family planned an Alaska cruise with 20 of us. My grandparents weren't able to join us at the last minute because of health concerns, so we printed life-sized photos of their faces and held them up in every family picture so it felt like they were still there.

Those photos still make me smile. They also remind me that we don't always know how many opportunities we'll have to travel together.

As a family travel advisor based in Kelowna, BC, I have the privilege of helping families across Canada plan vacations that bring generations together. Whether it's a cruise, a luxury all-inclusive resort, Disney, or an international adventure, I love helping families find the destination that's the right fit for the way they want to travel.

If you're thinking about planning a vacation with kids and grandparents, here's what I think every family should know before booking.

WHY MULTI-GENERATIONAL TRAVEL IS DIFFERENT

At first glance, planning a vacation for grandparents, parents, and little ones might not seem all that different from planning any other family trip. But once you start exploring destinations, it quickly becomes clear that there are more pieces to consider.

Some families are looking for adventure. Others picture slow mornings with a coffee and nowhere to be.

Young children often have very different energy levels than grandparents.

Even within the same household, everyone's idea of the perfect vacation can look a little different.

That's part of what makes multigenerational travel so rewarding.

It's also why these vacations deserve a little more thought before booking.

According to the Family Travel Association, more than half of parents say they're planning vacations that include both their children and their own parents, reflecting the growing popularity of multigenerational travel.

For many families, these trips aren't just vacations. They're opportunities to reconnect in ways that everyday life doesn't always allow.

AMANDA'S TAKE

One thing I've noticed is that families rarely remember how many activities they packed into the itinerary.

They remember watching the grandkids with Grandma and Grandpa, laughing over dinner and the stories they'll still be telling years later.

BEFORE YOU CHOOSE A DESTINATION

One of the biggest surprises for families planning a multigenerational vacation is that choosing the destination is often the easy part.

The harder part is finding a vacation that feels right for everyone.

Some families dream about relaxing at a luxury all-inclusive resort. Others want to wake up in a new destination every morning on a cruise. Some have always imagined taking the grandkids to Disney. While another family is ready to explore somewhere completely new together.

Every family is different. That's why there isn't one destination that's perfect for everyone.

Families are often balancing things like:

• Different travel styles

• Different budgets

• Activity levels

• Mobility considerations

• Food allergies or dietary needs

• Ages ranging from toddlers to grandparents

These aren't obstacles. They're simply part of choosing a vacation that's the right fit for your family.

GOOD TO KNOW

Connecting rooms, larger family suites, and some cruise cabin categories are often among the first accommodations to sell out, especially during school holidays and peak travel seasons.

COMMON CHALLENGES FAMILIES DON'T ALWAYS EXPECT

Travelling with three generations doesn't have to be complicated. But it does come with a few unique considerations that many families don't think about until they start planning.

One of the biggest is that everyone's idea of a great vacation can be different. Some family members love full days of sightseeing. Others are happiest with nowhere to be.

Another common surprise is realizing that convenience matters more than families expect.

A beautiful resort may not feel quite as relaxing if restaurants, pools, and guest rooms are spread far apart. The same can be true for destinations that involve long walking days or busy schedules.

None of these are reasons to avoid travelling together. They're simply reminders that the best multigenerational vacations are often the ones that are chosen thoughtfully.

And that's where choosing the right destination can make all the difference.

SETTING EXPECTATIONS BEFORE YOU TRAVEL

One conversation before your trip can prevent a lot of frustration once you arrive.

Talk about what everyone expects from the vacation.

Grandparents may picture leisurely breakfasts and quiet afternoons. Kids may be counting down the days until they can spend hours at the pool and water park. Parents are often hoping for a little of both.

None of those expectations are wrong. They simply need to be shared.

One of the easiest ways to avoid disappointment is to decide ahead of time which moments are important to spend together and where everyone has permission to do their own thing.

Maybe everyone meets for dinner each evening. Or mornings are spent together while afternoons are more flexible.

Maybe one group heads off on an excursion while another enjoys a relaxing day by the pool.

There isn't a right answer.

A successful multigenerational vacation doesn't mean spending every minute together. It means making sure everyone comes home feeling like they had a wonderful vacation.

GOOD TO KNOW

Even if every household is paying separately, I always recommend having one person coordinate the overall booking.

It makes it much easier to keep track of:

• Room requests

• Dining reservations

• Excursions

• Transportation

• Important travel dates and deadlines

Having one point of contact helps the planning process run much more smoothly.

UP NEXT: WHICH DESTINATIONS WORK BEST FOR MULTIGENERATIONAL FAMILIES?

Cruises.

Luxury all-inclusive resorts.

Europe.

Alaska.

Disney.

Each offers a very different experience, and each can be the right choice depending on your family's travel style.

Let's take a closer look at what makes each one unique

CHOOSING THE RIGHT DESTINATION FOR YOUR FAMILY

This is usually the point where families start comparing destinations.

Should we take a cruise? Book an all-inclusive resort? Finally, plan that Disney vacation?

Or maybe this is the year to explore somewhere completely new together.

The truth is, there isn't one destination that's best for every multigenerational family. The right choice depends on the experience you're hoping to have together.

Some vacations naturally offer more flexibility. Others are ideal for families who want to stay in one place and truly relax.

Understanding those differences can make choosing a destination feel much less overwhelming.

Cruise Vacations

It's not hard to see why cruises have become one of the most popular options for multigenerational families.

Everything you need is in one place. You unpack once. Meals, entertainment, and transportation are all built into the experience. That simplicity appeals to many families, especially when different generations have different interests.

While the kids are making new friends in the kids clubs, grandparents might enjoy a quiet morning overlooking the ocean, and parents can finally slow down for a little while.

Everyone experiences the vacation differently, but it's easy to reconnect throughout the day.

For many families, that's one of the biggest advantages of cruising together.

AMANDA'S TAKE

One of the things I love most about cruises is how naturally they create opportunities to spend time together without feeling like everyone has to do the same thing all day.

Luxury All-Inclusive Resorts

If your family prefers settling into one beautiful destination instead of waking up in a new port each morning, a luxury all-inclusive resort can be a wonderful choice.

The best resorts make it easy to move between the beach, the pool, restaurants, and your accommodations without spending the day walking from one end of the property to the other.

That convenience often becomes more important than families expect, especially when travelling with young children or grandparents.

Many luxury resorts also offer a nice balance of family-friendly activities and quieter spaces, allowing everyone to enjoy the vacation at their own pace.

It's one of the reasons they've become such a popular option for multigenerational travel.

International Travel

Multigenerational travel doesn't have to mean a cruise or a beach vacation.

For some families, travelling somewhere completely new becomes the experience they'll talk about for years.

Whether it's wandering through a small European village, experiencing Tokyo, or exploring a destination that's always been on your family's bucket list, international travel offers something different.

The pace often changes. Meals become experiences instead of quick stops. History comes alive in ways children and grandparents can enjoy together.

The key isn't trying to see everything. It's allowing yourselves enough time to truly experience where you are.

Alaska

Alaska has always felt different to me.

Maybe it's the scenery. Maybe it's the slower pace. Or maybe it's because my own family's Alaska cruise reminds me that being together is never something to take for granted.

Watching glaciers drift past the ship or spotting whales from the deck naturally brings people together in a way that's hard to describe until you've experienced it.

It isn't a family getaway built around rushing from one attraction to the next. It's one that encourages you to slow down and take it all in.

Disney Vacations

Disney will always hold a special place in my heart because so many of my own childhood memories happened there with my grandparents.

It's one of the reasons I still love helping families experience Disney together.

For multigenerational families, Disney often works best when it's approached a little differently.

Rather than trying to fit everything into each day, many families find they enjoy the experience more when they slow the pace, build in time to rest, and focus on sharing the moments that matter most.

For families who choose Disney, where you stay can also have a significant impact on the overall experience. Being close to the parks often makes it much easier to return for a midday break before heading back out for the evening, especially when travelling with children who need a nap.

Still deciding between a cruise, a resort, or something more adventurous?

Every family is different, and choosing the right vacation is often the hardest part. If you'd like personalized recommendations based on your family's travel style, I'd love to help.

CLICK HERE TO BOOK A FREE CONSULTATION CALL

PLANNING FOR DIFFERENT NEEDS

One of the things I love most about planning family vacations is helping families think about the details they may not have considered yet.

Maybe Grandpa doesn't mind walking, but would appreciate a resort where everything is close together.

OR Maybe your child has a food allergy and you want to know they'll be able to enjoy meals without stress.

Maybe your family simply has different energy levels.

Those aren't obstacles. They're planning considerations. Each family has its own unique set of family needs. The right destination takes all of those into account before anyone packs a suitcase.

If your family is travelling with mobility, medical, or sensory considerations, you may also find my guide to planning an inclusive family vacation helpful. It explores some of the questions to think about before choosing a destination.

Food Allergies & Dietary Needs

Sharing meals is often one of the highlights of a family vacation, so it's understandable that dietary needs can feel like a source of stress before you travel.

The good news is that many cruise lines, resorts, and family destinations have made significant improvements in accommodating food allergies and dietary restrictions. While the level of support can vary, travelling with dietary needs is often much more manageable than families expect.

It's simply another factor to consider when choosing the destination that's right for your family.

Mobility

Accessibility isn't just about wheelchairs.

Sometimes it's simply choosing a destination with shorter walking distances, elevators, or easy transportation so everyone can comfortably enjoy the vacation.

Small planning decisions often have the biggest impact.

WHICH VACATION IS RIGHT FOR YOUR FAMILY?

Every destination offers something different.

Cruises make logistics simple.

Luxury all-inclusive resorts offer relaxation and convenience.

International travel brings opportunities for discovery.

Alaska encourages families to slow down.

Disney creates the kind of magic that many families dream about sharing together.

There isn't one destination that's "best." Only the one that's the best fit for your family.

THOUGHTFUL PLANNING MAKES A DIFFERENCE

One thing I've come to appreciate is that it's often the small details that shape a family's experience.

Sometimes it's choosing accommodations that are easy to get around. It's knowing a destination can comfortably accommodate dietary needs. Or finding a vacation where everyone, from toddlers to grandparents, can enjoy themselves without feeling rushed and built in downtime.

Those details may not be the first things families think about when they start dreaming about a vacation.

But they're often the things that help everyone relax once they arrive.

FREQUENTLY ASKED QUESTIONS

What's the best vacation for kids and grandparents?

The best destination for your family vacation is the one that matches your family's travel style, interests, and pace. Cruises, luxury all-inclusive resorts, international adventures, Alaska, and Disney vacations can all be great choices.

How far in advance should we start planning?

Larger family groups often benefit from planning earlier, particularly when travelling during school holidays or looking for connecting rooms, larger suites, or specific cruise accommodations. 12 - 18 months in advance is a good time to start have conservations and start planning.

Is Disney a good choice for multigenerational families?

Absolutely. Disney can be a wonderful choice, particularly when the pace of the trip allows everyone to enjoy it comfortably.

Can multigenerational travel work if someone has mobility or dietary considerations?

Yes. Many destinations are well equipped to accommodate different needs, which is one of the reasons thoughtful destination selection can make such a difference. 

A FINAL THOUGHT

When I think about travelling with my grandparents, I don't remember every attraction we visited at Disneyland. I remember my grandpa biting into that frozen banana and how hard we laughed.

Years later, when we held life-sized photos of my grandparents on our Alaska cruise because they couldn't be there, it reminded me how quickly seasons of life can change.

Those two trips shaped the way I think about family travel.

The destination matters. But sharing those experiences together matters even more.

If you're planning a vacation with kids and grandparents, I'd love to help you find the destination that's the right fit for your family, not just the most popular one.

Whether you're considering a cruise, a premium all-inclusive resort, Disney, or an international adventure, thoughtful planning can make all the difference when you're travelling with multiple generations.

NOT SURE WHERE TO START?

If you're travelling with mobility, medical, or sensory considerations, my guide to Planning a Family Vacation with Mobility, Medical or Sensory Needs can help you think through the details before choosing a destination.

READY TO START PLANNING?

If you're looking for personalized advice and want help choosing the right vacation for your family, I'd love to help.

Whether you're still deciding where to go or you're ready to book, we can work together to create a trip that matches your family's travel style, budget, and priorities.

You can get started by:

• Booking a complimentary consultation to talk through your vacation ideas and explore the best options for your family.

• Joining my free Facebook community, where I share family travel tips, destination inspiration, and practical advice to help busy families travel with confidence.

When you’re ready, I’m here to help you narrow options and bring it together seamlessly.

Because multigenerational travel deserves to be done well.