Multi-Generational Travel Loading…

Planning multi-generational travel is like packing for a picnic, a marathon, and a sleepover – all at once. I’m currently planning an epic overseas adventure with three generations: my late 60ish mum, my preschooler daughter Kaydes, and 40ish me.

I’ve spent lots of time plotting, pinning, and scrolling through maps, travel blogs, and late-night wishlists. There’s the thrill of adventure, sure – but also a fair bit of behind-the-scenes sweat. Think sleep times, mobility considerations, snack logistics, and the eternal question: will everyone enjoy this?

The first month is just me and Kaydes. Soaking up sun in Fiji, chasing waves in Oahu, and zig-zagging through the US and Canada. But the real multi-generational travel magic begins on September 9, when we all touch down in Dallas. We’ve given ourselves three nights there so Mum can shake off any jet lag and settle in, before we dive headfirst into a whirlwind of cultures and landscapes: Mexico, Peru, and beyond.

Three generations. One itinerary. A million tiny considerations. From keeping Kaydes entertained and curious, to making sure Mum has downtime and has her daily chats to Dad, to carving out space for myself. I’m dreaming of my favourite massage in Cusco, and yes, Mum’s babysitting! It helps that we’ve lived and travelled together before, but never quite like this…

Here’s how I’m prepping our multi-generational travel to make it joyful, flexible, and (mostly) meltdown-proof.

1. Adventure Meets Downtime

Tip: Create a rhythm that suits early risers, early nights, and everything in between.

Kaydes is up with the sun – wide-eyed and ready to roll – so Mum and I will be up and out early too. The silver lining? We’ll hopefully beat the crowds and have magical spots all to ourselves!

We’re front-loading our days with the must-sees. That way, if Kaydes hits the wall later on, we’ve already ticked off the big ticket items. Anything we manage after lunch? Bonus. We’ll have a backup list of spots we would also love to see, in case Kaydes surprises us with extra stamina. There are a couple of day trips – but our default setting will be this gentle rhythm. It’s so tempting to squeeze it all in, but too much activity = burnout.

Late afternoons are for slowing down – books, naps, snacks, or a cheeky treat at a local café while Mum and I regroup. We’re aiming to be back at our accommodation by late afternoon most days. That gives us time to prep dinner, daily calls back to NZ, and get Kaydes settled for bed. I’ll be wrangling the bedtime routine while Mum calls Dad, and gets that moment of connection, which matters just as much as any stop on our itinerary.

2. Accommodation with Heart – and a Washing Machine!

Tip: Prioritise space, comfort, and character.

Accommodation is probably where I’ve put in the most time – and for good reason. Each place needs to be safe for Kaydes, charming enough to delight Mum, and ideally come with a view (for me and my morning energy drink rituals). I’m booking stays with heart and personality – no cookie-cutter hotels here. Think an Encanto-style casita in Valladolid or an alpine cabana in El Calafate. Bonus points if there’s a washing machine and some quirky detail that makes it feel uniquely local.

The must-haves? A kitchenette or similar for longer stays, and definitely twin or triple beds. I’m requesting cots for Kaydes, though let’s be honest – she’ll probably end up beside me anyway. Some places have separate rooms, but more often we’ll be sharing a space – and honestly, I love that. There’s something comforting about all being together at the end of a big adventure day.

We’re going carry-on only for the whole trip – the only way to travel! (And yes, I’ve got a post coming on that.) Since we pack light, we don’t need loads of room. It’s about choosing spaces that feel lived-in rather than passed through – where the accommodation becomes part of the story. I want each stop to feel like we’ve landed somewhere special, not just another pin on the map.

3. Short Travel Days > Epic Itineraries

Tip: Don’t try to do it all. Your future self will thank you.

One of my biggest goals? Keep travel days short and sweet. Back-to-back transfers and rushed connections? Nope. I’ve mapped out a mostly forward-moving route with minimal backtracking, always aiming for direct options. Long travel days can zap the fun out of an adventure, so we’re sticking to shorter hops, gentle pacing, and plenty of breathing room. I’ve basically mastered Kayak’s “Sort by Quickest” filter. If we must do a big day, I plan to follow it with a chill one.

Because Kaydes is up with the sun, I plan for morning or midday departures. It might sound hectic, but it works – we usually get to our next spot early enough to settle in, stretch our legs, and get to bed before overtiredness sets in.

If a longer travel stretch sneaks onto the schedule, I pair it with a rest day. No checklist, no pressure – just us, landing somewhere new and easing into the rhythm. The goal isn’t to tick boxes. It’s to travel in a way that feels good for all of us.

4. Food = Mood

Tip: Everyone’s happier when there’s something tasty (and familiar) on the table.

Most of the places I’ve booked include free breakfast – a total win. We’ll be making the most of those morning spreads, and probably sneaking a couple of fruit pieces to go (travel mum hack 101). It’s one less meal to plan and a nice way to ease into the day together.

Whenever we land in a new country, our first mission? Supermarket run. I’ve pinned a bunch already – prepped for the little snack monster I live with. We’ll stock up on familiar bits like Ricies or similar, and stash her go-to staples: cucumber, crackers, raisins, and fruit bars. They’re Kaydes’ comfort snacks, and honestly? Mine too.

I’ve booked places with kitchenettes whenever I could. I’m sure there’ll be something comforting about slicing up fruit or whipping up pasta in a new country. Some kind of normalcy when everything else feels foreign! I’ll also keep a stash of crackers, raisins, and bars in my backpack – because nothing derails an idyllic travel moment faster than a hangry kid. Snacks are my secret weapon—and yes, I hoard fruit bars like a squirrel with anxiety! 😂

5. Playground Prep

Tip: Save nearby playgrounds in your maps app before you even arrive.

If you’re travelling with kids, this one is pure gold. Whenever I book a new city or town, I always scout playgrounds ahead of time and save them in my Apple Maps app. A morning of sightseeing? Follow it with 45 minutes on the swings. Everyone wins. It’s her “normal,” and it helps her process everything new.

It has been a total sanity-saver. Whether I’m in a hectic city square or a sleepy village, knowing where Kaydes can run, climb, and let off steam makes all the difference. Best playground so far? The one next to Sagrada Familia. Kaydes played with local kids, and I got a Gaudí backdrop. Win-win!

Some of our best times have been in those everyday places – watching Kaydes make friends with kids who speak other languages, seeing her confidence grow, and just pressing pause on the travel pace.

6. Divide and Conquer

Tip: It’s OK not to do everything together.

Three people. Three energy levels. One itinerary. Something’s gotta give.

Sometimes, togetherness will mean time apart. Kaydes and I might head to a playground while Mum explores a nearby gallery. Or Mum watches a movie in the room with Kaydes, while I go for a massage. Giving each other breathing room makes our shared time sweeter.

Some days we will all do the same thing – like a scenic train ride or a day at Machu Picchu. But there will be days when it makes more sense to split up. There’s no gold star for doing everything together. Sometimes the best bonding comes after a little breathing room.

7. Embrace the Unexpected

Tip: Leave wiggle room. Some of the best memories come from detours.

The biggest lesson I’ve learned from solo travel, parenting, and life in general? Leave room for magic. Things will go sideways. We may have our bags checked in and get delayed, grumpy mornings, and at least one epic meltdown – likely mine! But we’ll also have belly laughs, spontaneous dance parties, and quiet moments watching the stars.

That’s why I’ve built in buffer days, slow mornings, and the occasional “do nothing” day – especially in places where the scenery alone is worth the stay. That way, when things do go off-script, we won’t be completely thrown.

Some of my favourite travel memories have come from the unplanned stuff – a surprise street festival, a stray cat Kaydes fell in love with in Bali, a wrong turn that led to a view we wouldn’t have found otherwise. These are the moments that stick – not the perfect plans, but the beautiful surprises in between.

8. Keep the Bigger Picture in Focus

Tip: This is about more than ticking off places – it’s about growing closer.

At the heart of all this planning and pinning and packing is something simple but profound: this multi-generational travel is a gift. Everyone has a voice, and has picked a couple of places they would like to visit. Mum is dreaming of Tikal, Guatemala and Machu Picchu, Peru. Kaydes? Disneyland, of course!

It’s a chance for my mum to make memories with Kaydes in places neither of them have seen before. It’s a moment for me to share the world with both of them, to show Kaydes that family comes in many forms – across generations, borders, and breakfast preferences!

Bonus Tips for Multi-Generational Travel Planners

💡 Medical Prep
Prepare everyone’s key medications, and extras just in case. Check vaccination requirements early, especially for countries with specific health regulations.

💡 Comfort Anchors
A favourite toy, a familiar snack, or even my favourite Contact Lens case can soothe homesick hearts – young and old-ish.

💡 Itinerary Sharing
We’ve been using the TripIt app to share our travel dates, addresses, and daily plans.

💡 Overseas Logistics
Work out how you’ll pay for things overseas. Mum and I are going to use Revolut overseas, and will buy a global eSIM through the app, that will work in every country we’re visiting.

💡 Leave Room for Surprise
Don’t overshare every detail in advance – try to keep a few fun moments up your sleeve for spontaneous delight. I still kick myself that I told mum that we are going to go line dancing in Fort Worth! 🙈

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Have you ever done multi-generational travel – family, friends, or both? What worked, what flopped, and what would you tweak next time? I’d love to hear your stories!