2 Months of Multi-Gen Travel: The Good, the Hard, & the Unexpectedly Funny 👵🏼👩🏼👧🏼

Travelling as a single mum already feels like a bold adventure. Add my mum into the mix and you suddenly have three generations navigating airports, border crossings, and supermarket food decisions. It’s a travelling trio dynamic that probably shouldn’t work as well as it does, but somehow it really does.

Over two months, we crossed countries, climates, and quite a few time zones! We kept up our usual tradition of travelling carry-on only – one shared suitcase with “her side and my side,” plus my camera backpack. Mum met the brief also and travelled carry on only.

Here’s how it all unfolded.

THE GOOD

The best part was travelling with two of my favourite ladies. Simple as that. One of my proudest moments was taking them to places I’d visited nine years ago. I walked those same streets with Kaydes’ small hand in mine and Mum beside us, feeling that quiet sense of things coming full circle. It made me think about how much life can change and still somehow carry you right back.

It was also wonderful to see ideas turn into highlights. One night researching for the trip, I stumbled across line dancing in Fort Worth at Billy Bob’s, North America’s largest honky-tonk bar. Mum loves line dancing, so actually seeing her walk straight from the street, into Ed Sheeran’s Shivers line dance made me so happy. We all joined in at some point, loving the vibe of the place and not wanting to go back to our accommodation!

Seeing wildlife in the wild was a huge highlight for us all. In Tikal, Guatemala, Kaydes spotted spider monkeys swinging in a tree like acrobats on a mission eating berries. Her face lit up, and honestly, I don’t know who gasped louder – her or me. Seeing the world through her eyes still delights me to no end.

Having another adult with me proved invaluable when we had one of those once-in-a-lifetime wildlife experiences in Peru. In the Palomino Islands, I got the chance to swim with a massive sea lion colony. While originally I declined the option, I figured what a way to finish my last day in Peru! Mum encouraged me too, so before I knew it I was jumping off a boat and being surrounded by dozens of curious, playful sea lions in the turquoise water!

We also discovered I had what Mum nicknamed “blonde power.” It became the running joke of the trip, the way people were kind, helpful, and patient with the little blonde lady accompanied with her daughter and mother. Directions, tickets, favours… I’d ask, and somehow doors opened. I still don’t understand how, but we’ll take it!

We had sunshine in almost every place we landed. Warm mornings, balmy evenings, gentle breezes. It made everything easier. And the food? Oh, the food. We fell in love with a tomato relish Mum’s going to try and recreate, and I would like to try and make a jam that we loved in Lima.

These were the memories that settled in deep, the good, simple ones that make the whole adventure feel worth every early start.

THE HARD

Travel isn’t perfect, and ours definitely had its prickly edges. Land border crossings in Latin America tested us every which way. Lines, multiple passport checks, random questions, language barriers, exit and entry fees, and that eternal limbo where you stand there thinking, please just let us through so I can get this child a snack!

Flights were another plot twist, especially in Argentina. Airlines changed schedules without warning, cancelled things, moved airports, or delayed departures. One major delay fell on Kaydes’ fourth birthday. We spent more than two hours in the airport while everything was sorted. Luckily, there was a wonderful playground that kept her cheerful. And the airline did put us up in a nice hotel and covered our meals, so the day ended on a brighter note.

Travel isn’t just long lines and delayed flights, sometimes it’s about navigating the unexpected ouch moments too. A couple of scares had us considering whether we might need to cut the trip short. I have Osteoporosis and thought I’d broken a rib leaning over a bus seat. It was possibly just a hairline fracture, and would heal like my last one. We kept an eye on it, just in case. *NB I still need to get that checked out!

Mum slipped back and cut her head a little on one of our mornings in Cusco, which sparked a moment of panic. Seeing her hurt made me realise just how much I struggle when things go wrong. I get scared. I get frustrated. And in those first few moments, I’m pretty sure I was short with Mum, which is awful. It reminded me how emotionally raw I can be when faced with injuries or sudden crises, and how important it is to pause, breathe, and care for everyone — including myself.

Around the six-week mark, I noticed the fatigue creeping in for all of us, especially Kaydes. When you’re far from home, even lovely days can feel big. She struggled some days and wanted the comfort of home, her things, and familiar rhythms. I understood it completely, even if we couldn’t head back immediately due to being deep in Patagonia at the time.

The hard moments didn’t define the trip, but they did shape it. They reminded me that travel isn’t a glossy highlight reel. It’s real life, just lived elsewhere.

THE UNEXPECTEDLY FUNNY

In Puerto Maldonado, I booked a place without noticing that it came with two red-footed land tortoises that live there. Their names were Pandemio and Arteris, and they became instant friends of the family. Watching Kaydes feed Pandemio grapes is still one of my favourite snapshots of the whole trip. He chomped like a tiny ancient king who’d waited all day for that single grape. Her surprise and love for him was everything.

Then there was her fourth birthday in Buenos Aires. I bought her a big unicorn balloon shaped like the number four. I did not expect it to become her sidekick for half the day! We carried it through the city, took photos with it, and even brought it straight into Café Tortoni, with its chandeliers, marble columns, historical charm… and a rainbow unicorn “4” balloon bobbing along with us! I could feel people smiling. It was joyful in the silliest, sweetest way. Mum’s already had a go recreating the Selva Negra chocolate cake we enjoyed there!

And then there was Tikal. We woke at 3.45am for a 4.30am minibus departure to reach Templo IV just after sunrise, without the even earlier proper sunrise tour. We took a quieter track toward the temple, and while I’ve dreamed of seeing a jaguar in the wild… I was praying very sincerely that one didn’t appear on our path! With my heart thumping, I piggybacked Kaydes while Mum kept pace behind, and we walked briskly in silence for 20 minutes!

Inside my head was a full debate: Do you stay still if one comes up? Do you run? Why didn’t I Google this on the bus?!!
Spoiler: no jaguar. Just me, slightly stressed, slightly sweaty, and relieved when the trees opened and Templo IV appeared!

These little moments – the tortoises, the balloon, the silent jungle march – brought humour into our days and lightness into the tough ones.

WHAT MULTI-GEN TRAVEL TAUGHT ME

I learned that plans will wobble, patience will thin, and someone will always need food or the bathroom at the exact wrong moment!

But I’ve also learned that joy grows in the overlap. Mum brought patience when mine was running on fumes. I brought structure when she was distracted by a bakery. Together we formed a bubble where Kaydes felt supported, entertained, and safe.

Travelling with three generations isn’t all smooth. It isn’t quiet. It isn’t predictable. But it’s layered with connection. It’s full of tiny moments and memories we’ll carry for years.

TIPS IF YOU’RE PLANNING MULTI-GEN TRAVEL

I thought I’d add a few things we learned the hard way, in case you’re about to go on a multi-gen trip. Nothing fancy, just the kind of stuff I wish someone had whispered in my ear before we set off.

Pack lighter than you think.
Every extra item becomes a team problem. Carrying less kept us calmer, faster, and able to pivot when things went sideways.

Choose flexibility over perfection.
The “perfect” planned out days never turned out to be the best ones. The best ones happened when we wandered, slowed down, or followed something unexpected – like two random resident tortoises, or swimming with a sea lion colony!

Book buffer days.
Especially when crossing borders, moving between climate zones, or switching time zones. Give yourself space to rest before diving into the next big adventure. I was so grateful for the few washing days in city apartments, where Kaydes basically stayed inside and blobbed out, and Mum or I did the local supermarket runs.

Food is its own form of diplomacy.
Hungry child? Snack. Tired nana? Picnic stop. Mum losing patience? Something sweet usually works! I swear 80% of the trip was improved by a well-timed snack!

Have a plan for the “what ifs.”
Flight changes, delays, or border issues hit harder when you’ve got two generations depending on you. Even a loose backup plan makes you feel steadier. We also figured it was the ‘god finger’ saving us from possible bigger problems, and as long as we were safe, we were good.

Expect emotions.
Kids miss home. Adults get tired. Someone will cry at some point, and honestly, it might be you. It’s all normal.

Find the tiny joys.
They’re the glue on long trips. A funny sign. A perfect relish. A tortoise with strong opinions. A unicorn balloon bobbing past people. These are the bits you’ll keep.

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Travelling with three generations isn’t about getting everything right. It’s about finding a rhythm that works for you, holding space for each other, and letting the trip shape itself a little.

And because no trip is complete without a little silliness, I put together a short travel dance video of us dancing our way through different spots along the trip. Expect lots of laughs, a few questionable moves, and pure joy. You can watch it here:

If you’re planning a multi-gen trip, what are you most excited about, and what secretly worries you the most? Drop a comment below.