Why Multigenerational Family Trips Are Harder to Book Than You Think

I get a lot of enquiries that start the same way: "We want to plan a trip where Grandpa and the kids all come. Nothing fancy, just somewhere everyone will enjoy."

It always sounds straightforward. But here's what I know from planning hundreds of these trips: multigenerational travel is exponentially harder to execute than single-generation family travel.

Not because there's anything wrong with the idea. Because the logistics are actually complex, and most of the travel industry has no idea how to handle them.

The problem with three generations at one table

When you're planning a trip for just parents and young children, the variables are fairly contained. Nap schedules. Early dinners. Bath time. You're solving for one family unit.

Add grandparents and everything changes.

You've now got people with wildly different physical capabilities. A five-year-old who wants to run around. A seventy-year-old who needs to rest. A parent who wants to feel like they're on holiday, not managing logistics.

You've got different spending expectations. What feels like splurging to one generation feels like ordinary to another. These conversations never happen until you're on the trip and it's too late to fix it.

You've got different interests that don't naturally overlap. Grandpa wants a quiet resort with golf. The kids want activities and animation. Everyone's polite about it, but you can feel the tension.

And you've got the timing problem. When is everyone actually free at the same time?

What usually goes wrong

I've seen families book beautiful resorts that completely miss what makes a multigenerational trip work. They pick a place because it's luxurious, or because it's where they went on their honeymoon, or because their friends recommended it.

Then they arrive and realise: the resort has no golf, so Grandpa's bored. The animation is constant and exhausting, so Grandma retreats to the room. There's no quiet area for the adults to have a proper dinner while someone looks after the kids.

What they've done is booked a nice place. What they haven't done is plan a multigenerational experience.

The difference between booking a resort and planning a trip

Any travel platform can book you into a resort. But that's not the same as planning a multigenerational trip that actually works.

Planning one means asking the questions nobody else asks. Can a grandmother with mobility issues get from the room to the beach? Is there a lift, or is that "ground floor" room actually up a flight of stairs?

It means understanding the daily rhythm. It means budgeting properly — not just for the resort, but for the setup that makes everyone's life easier. Ground floor rooms cost more. Villas cost more than hotel rooms.

And it means understanding the family dynamic. Is this trip about everyone doing everything together, or about giving people the freedom to do their own thing? Because those two trips look completely different on the ground.

Why you need someone who's planned these before

The difference between a good multigenerational trip and a chaotic one usually comes down to one thing: someone asking the right questions and understanding what the answers actually mean.

A booking platform doesn't do this. A generic travel agent doesn't do this. Even a luxury hotel doesn't do this — they're thinking about their property, not about your actual family experience.

Someone who's planned dozens of these trips knows which resorts have that quiet corner where the adults can eat properly, and which property's "family animation" is actually constant and exhausting versus one that lets families opt in.

Most importantly, they know that a multigenerational trip isn't a problem to solve. It's an experience to design.

If you're thinking about it

If you're at the stage of "we should do a multigenerational trip but I have no idea how to actually make that work," that's exactly the right moment to talk to someone who's done it properly before.

Because honestly, these trips can be absolutely wonderful. But they need real planning — the kind that starts with a proper conversation about what everyone actually wants, what everyone can actually do, and how to make all three generations feel like they had a genuinely good time.

Not just like they tolerated each other at the beach for a week.

Byline: Nicola Evans is the founder of 6Teen Summers, a luxury travel advisory based in Newport Beach, California. She specialises in multigenerational itineraries for families, couples, and groups.