Why Generational Travel Is One of the Most Meaningful Trips You Can Take

My mom is turning 90. To celebrate, the 2 of us slipped away for a few quiet days at One&Only Palmilla in Los Cabos.

It was just us, the ocean, long meals and nothing on the schedule.

What I loved most was the uninterrupted time with her. The older we both get, the more I want days like that.

Travel slows down when you go across generations. Conversations run longer. And the moments you remember later are usually the simple ones.

Why multi-gen is our jam

I've planned a lot of multi-generational trips, and I have a personal reason to love them. My very first trip to Africa, in 2010, was a safari my parents surprised Dan and me with. We're still telling stories from it 15 years later.

When families travel together like that, grandparents get real time with their kids and grandkids. Parents see their own parents differently. The kids hear stories that never come up at home. And dinner goes on for hours.

Our clients tell us these are the trips they remember most. The grandkids trying something new with Grandpa. Everyone around one table after a big day.

Why these trips get complicated

They're also some of the hardest trips to plan.

Everyone needs something different. Grandma wants a quiet morning by the pool. The teenagers want adventure. People fly in from different cities on different schedules, and everyone has an opinion about the rooms.

I saw this on that 2010 safari. Dan and I loved Tubu Tree in Botswana, with its raised tents and walking and water activities. My parents found the steps hard, and they really wanted a comfortable seat in the vehicle and their eyes on the animals. So we moved on to King's Pool, which suited them much better. Same trip, different travelers.

The small details add up fast:

Are there connecting rooms so the family can stay close?

Is there a big suite where everyone can gather?

Do the arrival and departure dates line up, so you actually get time together?

Without someone coordinating, planning turns into a never-ending group chat about flights.

What makes them work

Room to spread out. You're in your room more than you think, and with 3 generations, rooms REALLY matter. Some luxury ships have big multi-bedroom suites with a living area, so the family can gather and still have private bedrooms when someone needs a break. On land, connecting rooms or a villa work well.

One thing to know: some hotels won't guarantee connecting rooms unless they're booked that way from the start. That's the kind of detail we watch for.

Everyone arriving on the same day. It happens all the time. Someone books a different flight, arrives a day late and misses the dinner everyone planned around. Having one person watching the flights, transfers and rooms fixes that. That's my job.

Time together and time apart. The best multi-gen trips let people split up. Some sleep in or sit by the pool, others go explore, and everyone meets up again for dinner.

Where I'd send a multi-gen family

Luxury cruises work really well. There are cabins and suites for every branch of the family, plenty for each generation to do and dinner together every night. And if someone in your family says "I'm not a cruise person," a river cruise is a hotel that moves. AmaWaterways, Riverside and Tauck all have great ships and great food.

Private villas give you one shared home with room to gather and room to hide.

And a lot of luxury resorts are set up for families, with activities, quiet spaces and good dining, so every generation can do its own thing.

Through our Virtuoso partnerships, we can often add perks like room upgrades (when available) and extra amenities. When I planned Kurt and Randi Sue's birthday safari in Kenya and Tanzania, they were greeted with welcome notes, wine and cake at every hotel. They sent me photos every single time.

What I'll remember from Cabo

My mom and I didn't do anything big. We sat by the ocean, shared meals and talked.

That's the part I'll remember.

Tell me who you'd bring on a multi-gen trip, and where you'd take them.