"How much is this going to cost?"

It comes up in every multigenerational enquiry I receive. Not because anyone is being tight. Because every generation has a completely different relationship with money.

A seventy year old who has managed money for fifty years has firm views. A forty year old with a mortgage and school fees has other pressures. A ten year old has no idea what anything costs, and nor should they.

If nobody talks about it before you book, someone ends up feeling taken advantage of, someone feels guilty, and the money becomes the thing everyone remembers about the trip.

Most destinations are wonderful for one generation and hard work for another.

A lively beach town is fun at thirty and exhausting at seventy. A big kids resort is perfect with a five year old and a long week without one. A hiking destination is brilliant if you're fit, and miserable if your knees aren't what they were.

But some places work for every age at once. These are the five I come back to most for three generation trips.

There's a particular look on a grandparent's face when their grandchild sees an elephant for the first time. It's one of the reasons safari with three generations is one of my favourite trips to plan.

It's also one of the trips where the details matter most. The difference between a safari where Grandpa says "best trip of my life" and one where he's quietly uncomfortable all week comes down to a handful of decisions made before you book.

I came to Thanksgiving as an adult, having grown up in England without it. What I love most about it is that it's all about gathering, with none of the pressure of presents. It's one of the few times a year when the whole family is free at once.

Which is exactly why more families I talk to are choosing to spend it somewhere other than their own kitchen.

The hardest part of planning a multigenerational trip isn't choosing the destination. It's the fact that your seventy year old father and your twelve year old daughter want almost nothing in common from a holiday.

A twelve year old wants activity, other children, and something to talk about when she's back at school. A seventy year old wants quiet mornings, a good book, maybe a round of golf, and dinner somewhere he can hear himself think.

So how do you plan one trip where both of them have a lovely time?

Every year, around now, the same message arrives in my inbox. "We've just realised we haven't sorted Christmas. Is it too late?"

The short answer is that it's later than ideal, but it's rarely too late. You just have to plan a little differently.

Wondering if a travel planning fee is worth it for your family's trip? Here's what it actually pays for, and why it matters most on multigenerational trips.

Booking a trip where grandparents, parents, and children all have a good time sounds simple. It isn't. Here's why planning a multigenerational family trip is harder than most people expect and how to do it right.