Quote from Alex bobby on September 1, 2025, 5:05 AM

Three Generations, One Trip: The Beautiful Chaos of Travelling as a Family

Travelling with family is always an adventure, but when that family spans three generations, it becomes something entirely different — a blend of chaos, belly laughs, unexpected bonding, and surprising joy. Our recent trip to Montenegro proved just that: a whirlwind of experiences that taught us not just about a new country, but about the value of shared time across generations.

A Chaotic Start on the Adriatic

The moment that summed up our trip came early, soaring across the Adriatic by speedboat. My Boomer mum squealed with delight, grabbing onto me for support, only to clutch at my Millennial motherhood-induced belly rolls in the process. She laughed until tears ran down her cheeks, and I laughed with her. My eight-year-old, freshly scraped from a failed Parkour stunt on Our Lady of the Rocks island, stood tall in a superhero pose as the wind whipped his hair.

My Gen Z brother, whom I hadn’t been on holiday with in two decades, looked out at the looming Montenegrin mountains with tears in his eyes, overwhelmed by their beauty. My Gen X partner quietly rested a hand on his shoulder, steadying him in a way only family can.

It struck me then: there were no missing generations in this trip. This was our full spread, from child to grandparent, and our first real attempt at multi-generational travel.

The Rise of Multi-Generational Travel

It turns out we weren’t alone. “Multi-gen Megatrips” have been flagged as one of 2025’s biggest travel trends. The idea is simple: bring together multiple generations for one holiday, creating space to reconnect, strengthen bonds, and even heal old wounds. While it can be logistically daunting, when done right, it offers rewards that go far beyond a simple getaway.

Multi-generational living, of course, is not new. In many parts of the world, grandparents, parents, and children sharing the same roof is simply the norm. Data from Pew Research shows that more than 70% of young adults between 18 and 34 live with their parents in Italy, Croatia, Greece, Serbia, and Portugal.

By contrast, in the UK, the US, and much of Scandinavia — where my family is from — the nuclear family dominates. Living with parents as an adult is often unfairly stigmatized, equated with failure rather than practicality. But the pandemic shifted perspectives. By 2020, Britain had 1.8 million households with two or more adult generations, a rise of 38% in just a decade.

While permanent multi-gen living isn’t for everyone (I know my mum and I would struggle under one roof long-term), travel provides a bite-sized version of this experience. A week or two of shared meals, adventures, and downtime can deliver the benefits without the friction.

Choosing the Right Destination

Making a multi-generational holiday work requires one thing above all else: the right destination. It has to offer something for everyone — child-friendly activities, nightlife for the younger crowd, peace and comfort for parents, and accessible adventures for grandparents.

Montenegro turned out to be an inspired choice. Arriving in Perast, just a short drive or speedboat ride from Kotor Bay, we were instantly surrounded by surreal mountain scenery that seemed to enchant every member of the family, regardless of age.

We stayed at the Heritage Grand Perast by Rixos, a renovated palace overlooking the Adriatic. Its seafront pool became our hub of relaxation, while its restaurant kept everyone’s cravings at bay. For the first few days, simply soaking in the atmosphere was enough. By day three, however, we were itching for more.

Beyond the Tourist Hotspots

To experience Montenegro more authentically, we turned to Untravelled Paths, a tour agency specialising in local adventures. A speedboat ride revealed abandoned submarine tunnels and whisked us across Kotor Bay before we wandered through the storied streets of Kotor Old Town. Yet, it was outside the tourist-heavy areas that we discovered the heart of Montenegro.

Our guide, Ilija, introduced us to Susannah, a lifelong Montenegrin who opened her home to us for an evening of food, stories, and laughter. Together, we prepared a traditional polenta and fish stew, while she poured us glasses of homemade wine and her fiery plum liquor, Rakija. It was an evening of joy, conversation, and connection that none of us will forget.

Learning Through Adventure

As a home-educating mother, I wanted my son’s holiday to be more than just fun — I wanted it to be enriching. Ilija guided us to the Šćepanović Honey Farm near Kolašin, nestled among historic monasteries and the pristine Biogradska Gora National Park, one of Europe’s last primeval rainforests. It was the perfect blend of education and adventure.

Meanwhile, my mum chose quiet relaxation by the pool, my brother entertained my son (teaching him to swim by the trip’s end, a memory they’ll both carry forever), and my partner and I even managed to steal some rare, much-needed downtime thanks to our built-in babysitters.

The Unexpected Joy of Chaos

Of course, not every moment was perfect. Disagreements over where to eat cropped up regularly, and the pace sometimes felt overwhelming. But those small irritations paled in comparison to the joy of sharing Montenegro together. No one felt excluded, no one felt bored, and everyone left with a memory that belonged only to them — and to all of us collectively.

By the end of ten days, we found ourselves not just closer, but subtly transformed. Old tensions eased, new bonds formed, and a renewed appreciation for each other blossomed. Travelling as a “nuclear family” has its comforts, but multi-generational travel reminded us that family, in its widest sense, is worth celebrating while we still have the chance.

Looking Forward

As we left Montenegro behind, I couldn’t help but feel that this journey had been about more than just travel. It was about time — time shared between a grandmother and grandson, a brother and sister reconnecting, a couple rediscovering they’re balance, and a family weaving new stories together.

Looking forward, I hope this won’t be a once-in-a-lifetime adventure but the beginning of a new family tradition. Multi-generational trips may take extra planning, patience, and compromise, but the rewards — laughter, learning, and lasting memories — make it worth every moment of beautiful chaos.

Final Thoughts

Multi-generational travel is not without its challenges, but it offers something rare and precious: the chance to see the world through the eyes of those we love, at every stage of life. Montenegro gave us a backdrop of mountains, sea, and history — but what truly made the journey unforgettable was the laughter, the quiet moments, and the shared discoveries across three generations.

Travelling this way reminded me that family is not about perfection but about presence. The scraped knees, the belly laughs, the wine-fuelled stories, and the calm afternoons by the pool all stitched together into a tapestry of memories we’ll carry forever.

In the end, the beautiful chaos of travelling as a family turned out to be the very thing that made it perfect.

Conclusion

Travelling with three generations is undeniably chaotic, but it’s also deeply rewarding. Montenegro, with its mix of history, adventure, and natural beauty, provided the perfect backdrop for us to rediscover one another. If our experience taught me anything, it’s that multi-generational travel is more than a trend — it’s an opportunity to make the most of family while we have it.

For us, it’s something we’ll strive to do every year. Because when you’re lucky enough to have family spanning generations, there’s no greater gift than sharing time, laughter, and adventure together.