Generational Travel: When the People You Raised Become Your Travel Companions

There is something quite special about reaching a certain point in life and realizing that the people you spent so many years raising are now the people you want to travel with.

When the kids are little, family vacations are mostly about them.

You find a destination that works for everyone, figure out how to keep them entertained, make sure they eat something other than ice cream, and somehow get everyone out of the hotel room in the morning.

Then, almost without noticing, they grow up.

They have their own lives, their own jobs, their own relationships.

And suddenly, getting everyone together for a vacation becomes a completely different thing.

It is no longer about taking the kids on holiday.

It is about traveling with the people you have helped bring into the world.

And I think that changes the meaning of the trip.

Everyone has a different idea of a good vacation

The challenge with multigenerational travel is that you are rarely dealing with one travel style.

Grandparents might want to take things a little easier.

Parents might still want some adventure.

Teenagers might have absolutely no interest in whatever everyone else has planned.

Young children might need naps, snacks and breaks.

And the adults who were once children themselves might now have very strong opinions about what they want to do.

This is where I think pacing becomes so important.

Not everyone needs to do everything.

And not every day needs to be designed around the person who wants to do the most.

A good multigenerational trip should have enough flexibility for everyone to enjoy it in their own way.

Maybe one person wants to go hiking while another stays behind and enjoys the hotel.

Maybe some of the family wants to go rafting while others prefer a quiet afternoon.

Maybe everyone gets together for dinner.

That is perfectly fine.

The point is not to make everyone do the same thing.

The point is to give everyone a reason to enjoy being there together.

I think we sometimes confuse more with better

This is something I see a lot when people plan a big family vacation.

There is pressure to make it count.

If everyone has managed to get the same week off, flown across the Atlantic and made all the arrangements, then surely you need to make the most of it.

So the itinerary gets bigger.

More destinations.

More activities.

More early mornings.

More driving.

More things to see.

More things to tick off.

And eventually you have a vacation that looks incredible on paper and exhausting when you actually imagine living it.

Especially when you have several generations traveling together.

The eight-year-old does not necessarily want to wake up at 5:30.

The 70-year-old might not want to spend six hours in a car.

The 35-year-old might be perfectly happy doing both.

This is where I think the itinerary needs to take a back seat to the people.

The memories are the point

When you look back at a family trip ten years later, do you really remember how many activities you managed to fit into Tuesday?

Probably not.

You remember the things that happened around the activities.

The ridiculous joke that everyone kept repeating.

The dinner where everyone stayed at the table for hours.

The moment someone saw a sloth for the first time.

The wrong turn that turned into an unexpected discovery.

The swim.

The conversation.

The sunset.

The story that gets brought up every Christmas because everyone remembers it differently.

Those are the things that stay.

And perhaps that is one of the biggest differences between traveling with your family when you are younger and traveling with them later in life.

You become much more aware that getting everyone together is actually the rare thing.

The destination is important.

But the people are the reason you are there.

Costa Rica works particularly well for this

Costa Rica is an interesting country for multigenerational travel because you can build very different experiences around the same place.

One family member can spend the morning hiking.

Another can enjoy a slower breakfast and perhaps a spa or thermal experience.

Someone else can go wildlife watching.

Then everyone can meet up for lunch.

Or dinner.

Or simply spend the afternoon together.

You also have a huge variety of environments within a relatively manageable country.

Rainforest.

Volcanoes.

Beaches.

Wildlife.

Hot springs.

Rivers.

Small towns.

Adventure activities.

You do not necessarily need everyone to be interested in the same things.

You just need to find enough things that everyone is excited about, while leaving enough space for people to do their own thing.

And I think that is a much better way to plan a family trip.

The itinerary should serve the family, not the other way around

This is probably the biggest thing I would change about how people approach multigenerational travel.

Start with the people.

Who is coming?

What do they enjoy?

What do they not enjoy?

How much activity is realistic?

Who needs downtime?

Who wants adventure?

What are the things everyone genuinely wants to experience together?

Then build from there.

Not the other way around.

Because there is a temptation to start with Costa Rica itself.

You look at the map.

You see Arenal.

Then Monteverde.

Then Manuel Antonio.

Then perhaps Tortuguero.

Then the Caribbean.

And before you know it, you are trying to make six people with completely different rhythms follow one itinerary.

I would rather start with the family and work out what Costa Rica should look like for them.

Maybe that means fewer places.

Maybe it means staying longer.

Maybe it means having completely free afternoons.

Maybe it means splitting up for a few hours and coming back together later.

There is no formula.

That is kind of the point.

You don't get unlimited opportunities to do this

This is probably the more personal part of it for me.

Life has a funny way of making us believe that there will always be another opportunity.

Another Christmas.

Another birthday.

Another summer.

Another trip.

And hopefully there will be.

But there is something different about getting everyone together as adults.

People's lives get complicated.

Jobs.

Partners.

Children.

Distance.

Responsibilities.

Finding a week when everyone can actually be in the same place can become an achievement in itself.

So when you finally manage it, I think the last thing you want is to spend the whole week rushing from one thing to the next.

Take your time.

Have the long lunch.

Stay for another drink.

Let the kids disappear for a while.

Let the grandparents sit and watch the world go by.

Do the hike.

Skip the hike.

Change the plan.

Make a memory.

Because ultimately, I don't think the success of a multigenerational vacation can be measured by how much you managed to see.

It is measured by how much you enjoyed being together.

And hopefully, years from now, when everyone is back home and life has gone back to normal, someone will say:

“Remember that time in Costa Rica?”

And everyone will know exactly what they mean.

That, to me, is the trip.