Family Holidays in Greece: The Best Multigenerational Experience on the Water?

(and why a sailing holiday might just be the best of them all)

There’s a moment that happens on flotilla most weeks — you’ll have seen it if you’ve sailed with us before.

It’s early. The sun is only just stretching across the harbour. Grandpa and Grandma have already taken themselves off for a slow wander down the quay. They pause every few steps, chatting to the fishermen as they clear their nets from the morning haul. A gentle pace they remember from years ago… and one they still slip back into effortlessly when the heat, the light and the Greek way of life invite it.

Back on board, Mum and Dad are enjoying a quiet frappe — iced coffee in hand, the boat gently rocking, the teens mercifully still asleep. There’s a moment of silence that is almost sacred. A kind of peace that rarely exists in real life, unless you’re up before everyone else… which, let’s be honest, doesn’t happen much on holiday.

Eventually, the children begin to emerge — in stages, and at wildly different speeds.
The littlest ones appear first, of course. Already in their swimsuits, goggles on, fishing net in hand… nobody even asks how it got inside the cabin. Fishing before breakfast? Why not. They potter around the deck collecting treasures, dipping the net over the side, absolutely thrilled with the tiny silvery flashes darting beneath the boat.
A little later, the older kids surface — still half-asleep, but happy to take the little ones under their wing. Sometimes you don’t hear from them for hours until someone realises they’re hungry again.

Meanwhile, the teens finally emerge and — rather than gaming or retreating behind closed doors — they’re out on deck capturing everything on their phones, sending snaps and videos back home. “Look where we are.” “Look at this water.” “Look at this boat.” They move at their own speed, in their own language, sharing the experience in a way only they can.

And here’s the beautiful thing: on a sailing holiday, everyone gets their version of the perfect day… and you still meet in the middle.

Togetherness that doesn’t need planning

Multigenerational holidays often come with a funny kind of pressure.
Did we book enough? Did we plan enough? Will everyone enjoy it?
Is there too much activity? Too little? Will the kids get bored?
Will the grandparents get tired?
Have we spent the whole time juggling instead of relaxing?

A flotilla holiday solves all of that without you needing to try.

There are natural moments in the day where you come together — unforced, unplanned, totally simple.

The morning briefing, where everyone gathers on the quay.

All hands on deck as you slip the lines and leave port for the day.

Choosing a lunch stop based on the fresh tomatoes, olives and bread you picked up that morning.

Dropping anchor in a bay so clear the kids race each other to be first off the back of the boat — the older ones shepherding the younger ones in and out of the water with the confidence of seasoned mini-deckhands.

That slow taverna dinner, where the food might take a little longer than you’re used to… and that’s exactly the point.

It’s in the in-between moments — while you’re waiting for your saganaki, listening to a chorus of cicadas, watching dusk soften the whole harbour — that the conversations you never get to have at home suddenly surface.

Not the quick, transactional ones.
But the real ones.
The stories, the memories, the gentle teasing, the tales from “when we were young”…
The things that stick with you.

This is where multigenerational holidays matter.
This is where they make sense.

A pace for every generation

One of the most surprising (and delightful) things we hear every year is how well sailing naturally accommodates each age group.

Grandparents often rediscover that slower rhythm of life — a walk to the bakery, a quiet seat under an olive tree, a chance to chat to strangers in a way that feels almost impossible back home.

Parents get to exhale. To sit. To read. To enjoy a morning coffee without rushing out of the door.

Little ones get full permission to be little — fishing nets at dawn, goggles permanently attached, rock pooling on every beach, and that wide-eyed sense of adventure that makes every dinghy ride feel enormous.

Older kids rise to the occasion almost without realising — helping the young ones in and out of the water, pointing out fish, racing them to the bow, teaching them knots they’ve only just learned themselves.

Teens get freedom — real, safe, sunshine-filled freedom — and a sense of adventure that simply doesn’t exist in an all-inclusive resort or busy hotel.

But then…

You all reconnect.
Every single day.
Without forcing it.
Without someone playing cruise director.
Without screens getting in the way.

That’s the beauty of it.

The gentle art of SKI-ing ‘spending the kids’ inheritance’

Now… we approach this next bit carefully. With a smile and a wink — because, let’s be honest, we’re very aware of our own age as we head into our 50th season afloat.

But we can’t resist raising the topic, because it's one we've joked about with many of you.

You’ve probably seen the phrase on ski chalet walls:
“We’re busy 'S'pending our 'K'ids’ 'I'nheritance.”

Well, we dare you to ask your children — grown-up or not — this question:

Would you prefer…
a week or two making memories on holiday together?
Or an extra few hundred pounds in your bank account one day in the distant future?

We could almost put money on the answer.

Because when we watch families out on flotilla — truly together, laughing, eating, arguing gently about who lost the boat hook, swimming in bays that feel like secrets — it’s obvious.

It’s the time together that matters.
The shared adventure.
The stories you take home.
The photo of Grandpa teaching the kids to tie a bowline.
The teens helping the younger ones jump off the back of the boat (again).
The evenings in the cockpit playing cards until someone falls asleep mid-hand.

This is the inheritance they actually want.

The holiday you’ll all remember

A sailing holiday isn’t just a trip.
It’s a rhythm.
A gentle pull back to what matters.
A chance for each generation to move at their own speed and still arrive somewhere beautiful — together.

In a world that feels like it’s speeding up every day, this is one of the few holidays that slows everyone down just enough for something real to happen.

So whether you’re taking the little ones, the teens, the grown-up “kids,” or the whole clan in between…
A flotilla is the perfect setting for a multigenerational escape that doesn’t feel like hard work.
Just sunshine. Salt air. Adventure. Quiet moments. Long meals. And memories that settle in for life.

And who knows… maybe this is the year you “spend the kids’ inheritance” just a little.

If their smiles are anything to go by — we think they’ll thank you for it.

If you're ready to book your next adventure with the family, message the team today.