Big Family Vacations and Multigenerational Travel Memories

There’s something wonderfully chaotic, and deeply special, about big family vacations. Yes, they’re loud. Yes, they’re unpredictable.

But they also possess a kind of magic you can’t quite recreate anywhere else. Somewhere between the missed schedules, shared meals, and spontaneous laughter, something meaningful unfolds.

These trips aren’t just holidays. They’re living, breathing memory-makers.

The kind where conversations stretch across generations, where stories get retold (and slightly exaggerated), and where children quietly soak in family history without even realising it. In all the madness, there’s a rare kind of bonding that feels almost essential—something that shapes not just the present, but the generations to come.

I’ve just returned from one such trip with my husband’s family—four generations traveling together. From his 92-year-old grandfather to my five-year-old daughter, it was a beautiful mix of ages, energy, and perspectives.

And what an experience it was. Stories were shared, laughter echoed endlessly, and in between it all, we created moments that will stay with us long after the suitcases have been unpacked.

We took a dive into our community, gathering voices and stories on what makes these trips so unforgettable and why they hold such a special place in so many hearts.

My husband and I have two kids, and we love to travel. Now that my youngest is over two, we are finally able to prioritise travel more.

We try to take one trip as a couple and then plan another trip with our kids each year. Both of us come from big families, and we believe it is important for our children to bond with their grandparents, aunts, uncles, and cousins as much as possible, despite our busy schedules.

Growing up, family trips were always something I looked forward to. I have some of my best memories traveling with both sides of the family—my grandparents and cousins—around Thailand and the world.

Those trips were how I bonded with many of my relatives over the years. Back then, life felt more community-based, and we met more frequently at both sets of grandparents’ homes.

Families were bigger, and many of my cousins were close in age to me, so traveling together was always exciting.

I would love for my children to have similar experiences as they grow up. Each year, we take local trips with each side of the family.

These trips usually take place over a long weekend, are easy to plan, can accommodate babies and adults comfortably, and require minimal effort to organise. Because my youngest is only two, traveling locally with family has been the easiest option over the past few years.

Even simple trips to the beach or the mountains create unforgettable memories for everyone. Since these trips are local, they feel more relaxed, allowing everyone to switch off and spend quality time together.

When it comes to our immediate family, we plan international trips. As time goes on, however, I would love to organise an international trip with our extended family as well.

Although just thinking about planning for such a large group feels slightly overwhelming!

I’m very much in the ‘yay’ camp when it comes to big, fat family vacations. Maybe it’s because I’m close to a lot of my family, so being around them for days at a stretch doesn’t feel overwhelming.

It feels comforting, like slipping into something familiar.

Of course, it’s never perfect. Put that many people together and there’s bound to be a few disagreements, a bit of chaos, and maybe even someone getting annoyed over something small.

Plans don’t always go smoothly, and not everyone wants to do the same thing at the same time. But in a strange way, that’s part of the experience too.

Because when I think back on those trips, I don’t really remember the little bouts of drama. What stays with me are the moments in between: late-night conversations that go on longer than planned, everyone gathered around a table sharing food and laughing, or those completely spontaneous situations that somehow turn into the best memories.

There’s something about being with family in a new place that brings out a different side of everyone. You see people as they are, outside of routines and responsibilities, and that makes the connection feel even more real.

For me, those memories feel untouched. They stay with you in a way that’s hard to explain, and no matter how hectic the trip might have been in the moment, it always feels worth it in the end.

Since becoming parents, family travel has taken on a whole new meaning for us. Each year, we plan one big trip with my side of the family and another with my spouse’s side.

What started as small holidays has grown into large family adventures with grandparents, siblings, cousins, and children. With so many people involved, we usually start planning months in advance.

Before children, we travelled much more spontaneously. Now, with toddlers and grandparents in the mix, planning works better.

We keep a shared Google Doc where people add what they would like to do, which helps everyone feel included while still leaving room for a little spontaneity.

The best part of these trips is seeing the relationships that form across generations. Our children are not just spending time with us.

They are building real connections with grandparents, cousins, aunts, and uncles. There is something special about sharing everyday moments together on a trip—meals, car rides, walks, and quiet downtime—that help those relationships grow naturally.

But one of the greatest gifts travel has given our children is resilience. Our son started traveling when he was only six months old.

At first, it was hard. There were missed naps, unfamiliar beds, long flights, different time zones, and plenty of moments when things did not go according to plan.

Over time, though, travel taught him how to adapt. He learned that routines can change and that unfamiliar situations are not something to fear.

Now he is completely comfortable in airports, hotels, trains, and unfamiliar places. He can wait patiently for a flight, sit through a long train ride, try different foods, and adjust to a new schedule without much fuss.

I have realised that children are often more capable than we give them credit for. The more they experience, the more confident and flexible they become.

Travel teaches them patience, curiosity, and how to handle uncertainty. Those are skills that matter far beyond a holiday.

Some of our favourite memories have come from the biggest family trips. Last year, around 30 of us spanning four generations spent a weekend together at Dusit Thani Hua Hin.

It was loud, hectic, and wonderfully memorable to have everyone in one place. Another unforgettable family holiday was through Europe with my husband’s side of the family.

We all ended up flying into different countries—Switzerland, Sweden, and England, wherever the mileage tickets took us—before meeting up for a cruise to Norway and then spending a week together in London.

Coordinating so many people across different countries was an adventure in itself, but those are the trips we still talk about the most.

The older I get, the more I realise that the greatest luxury is not the destination. It is raising children who can move through the world with confidence, while making memories with the people we love.

As an expat who has spent most of my life away from home, I truly feel that family trips with grandparents are incredibly valuable, especially for the grandchildren.

These trips go beyond being just vacations; they create a rare and meaningful space to truly connect and bond, something that short visits back home often don’t allow.

During our recent trip with my in-laws to Jim Corbett and Dharamshala, I experienced this so beautifully.

Whether it was the thrill of early morning safari rides, trekking through the jungle, or simply enjoying a dip in the icy river flowing beside our cottage in Dharamshala, the excitement, giggles, and laughter were absolutely priceless.

We connected on a deeper level, sharing moments that turned into memories we’ll cherish forever.

There’s something special about being in nature—it slows everything down, allowing you to truly be present and spend uninterrupted time together.

It’s in those simple conversations about local food, bits of the local language, and shared experiences that the strongest bonds are formed, especially between grandparents and grandkids.

When it comes to traveling with multiple generations, there are certainly more things to consider.

We are a “plan everything” family, and with kids and grandparents, thoughtful planning makes all the difference.

For us, food is a big one. We love experiencing local cuisine, but my in-laws have dietary restrictions, so we make sure our hotel has suitable options for them.

In terms of activities, since my kids are still young, it hasn’t been too challenging yet.

We usually plan our itinerary so that during the first half of the day, all of us enjoy nature walks or museums together as a family.

After lunch, grandparents get to rest while we take the kids out for fun rides and activities.

It creates a balance that keeps everyone happy and energised.