The multi-generational trip is no longer a logistical challenge. It’s become the ultimate family adventure.
Something is shifting in the way we travel. According to new research, 25% of travellers now begin planning travel by thinking about how they want to feel instead of having a destination in mind. Instead of asking themselves, “Where should we go?” the question has become, “How do we want to feel when we get there?” And increasingly, the answer has everything to do with the people joining the journey.
For a growing number of families, that impulse is taking the form of a multi-generational trip. Not an ordinary family holiday, but an intentional journey – often built around a milestone, celebration or reunion. But just as often, it’s simply the recognition that time together is the most valuable thing a family has. Grandparents, parents and children spanning all ages. Everyone together, somewhere extraordinary.
It turns out that the desire to reconnect – to heritage, each other and experiences that feel genuinely human – is one of the most powerful forces shaping how we travel today. And these kinds of trips allow time to learn, explore and share evenings together in ways that everyday life rarely does.
It’s why luxury active travel company Butterfield & Robinson has created a Bespoke service specifically for this kind of group – the Multi-Generational Legacy trip. What makes such a trip feel so different from a regular family holiday? According to Kristi Elborne, Chief Experience Officer at Butterfield & Robinson, it’s the beautiful complexity of the group itself. “What makes multi-generational travel unique is the diversity of perspectives, energy levels and expectations all within one group,” she says. “At its best, Multi-Generational Legacy travel creates shared moments that become part of a family’s story, while also allowing space for individual interests and comfort. It’s not just about where you go, but how you bring people together in a way that feels meaningful for everyone.”
That balance, togetherness without rigidity, is also reshaping how families choose to travel. Yacht charters have become hugely popular, offering a shared home on the water alongside the freedom to explore each port at your own pace. Private estate rentals, which include villas, chalets and full property takeovers, give families a base to gather without living in each other’s pockets. And safari and wildlife journeys have emerged as a natural fit for multi-gen groups. “They offer a rare combination of education, adventure and shared discovery,” says Elborne, “where children, parents, and grandparents are all experiencing something new together in real time.” The common thread? Flexibility – the ability for each generation to engage in a way that suits them.
Where you go matters too, though perhaps not in the way you’d expect. Rich in culture, cuisine and the kind of unhurried beauty that appeals to every age, Italy and France remain perennial favourites. Croatia, Greece and the Galápagos are stunning settings for yacht-based adventures. And destinations like Iceland, Tanzania and Japan are drawing growing interest for their ability to astonish and engage across generations – these are places where a 10-year-old and a 70-year-old are equally wide-eyed.
For anyone planning their first multi-gen trip, Elborne’s most important advice might sound counterintuitive: You don’t all need to be together all the time. “The most successful Multi-Generational Legacy trips are designed around a balance of ‘time together, time apart,'” she says. “Different generations have different interests, energy levels and paces, and trying to force a single schedule can actually create friction.”
At B&R, that means designing days so that smaller groups can pursue what calls to them – whether that takes the form of a long bike ride, cooking class or an afternoon by the pool – before coming together again for the moments that matter most. “Those touchpoints are where the magic happens,” Elborne says, “creating space for storytelling, connection and shared memory-making.”
One final piece of advice: Start your planning early. The best multi-generational trips, the ones that feel effortless and extraordinary from the inside, are almost always the result of thoughtful planning and the kind of specialist expertise that turns a complex group dynamic into something seamless.
In a fast-moving and fragmented world, there is something quietly radical about gathering the people you love most and going somewhere wonderful together. Don’t think of it as a trip. See it as a chapter in your family’s story.
Learn more about what’s possible on a Multi-Generational Legacy at Butterfield & Robinson.