It can be extremely rewarding travelling with family. Not just with a partner, but across generations, with grown-up children, grandchildren, nieces or nephews, even close friends who feel like family. These trips carry their own kind of rhythm. They are not always simple, but when they go well, they create memories that last for years. 

Travelling with family after sixty can take many forms. For some, it is an annual holiday with a sprawling group and a shared house by the sea. For others, it is a quieter arrangement, a city break with an adult daughter, a walking holiday with a son, a weekend away with grandchildren. Whatever the shape, the intention is often the same. To spend time. To reconnect. To make space for shared experience in a world that is increasingly busy and dispersed. 

What makes these trips special is not just the destination, but the quality of the time together. Away from the demands of daily life, people soften. Conversations deepen. Laughter returns. There is something about being in a new place that invites us to see one another differently, not just as parent and child, grandparent and grandchild, but as travellers, companions, co-adventurers. 

That said, it helps to acknowledge that travelling across generations brings its own set of dynamics. Everyone has their own pace, their own priorities. A grandchild may be up at six, full of energy and questions. A teenager might prefer to sleep late and roam alone for a while. Adult children may carry their own ideas of how the trip should go, shaped by their roles as parents, professionals, or planners. The key is not to smooth out every difference, but to create space for everyone to be themselves. 

This often means loosening expectations. Not everything has to be done together. A morning walk alone can be as restorative as a group trip to the market. Some meals might be shared, others separate. If the plan is flexible, and the tone kind, these small differences become strengths, not tensions. They allow the group to breathe. 

For those travelling with young grandchildren, the joy is often in the small things. Watching them marvel at a train ride, a new food, or a wave washing over their toes. These are not grand adventures, but they matter deeply. They create a shared history that children carry with them into adulthood, a memory of time with you that is theirs alone. 

Travelling with adult children can be equally rewarding, but in a different way. It is a chance to relate not as parent and child in the old sense, but as two people side by side. The conversations may be more reflective, the activities more evenly shared. There may even be role reversals, with your children booking the accommodation or guiding the route. This, too, can be a gift, a way of seeing how they have grown, and how you have changed together. 

There will be moments of miscommunication, of course. Tiredness, different priorities, the occasional clash. But with generosity and humour, these tend to fade. What remains is the experience. The chance to step outside of your normal lives and into something shared. A street wandered. A meal cooked together. A joke repeated. A photo that becomes more precious with time. 

Travelling across generations is not always smooth. But it is nearly always worthwhile. It reminds us that family is not just made up of roles and responsibilities. It is made up of stories. And some of the best ones begin with a suitcase, a little patience, and the decision to go somewhere together.