Why your 30s and 40s are the best time to travel with your parents

Andrew Dickens

We’ve all tried holiday rentals, but what about a holiday with the ‘rentals? If you think you’re too old, too cool or too likely to spend your holiday regressing to the point where you lock yourself in your room and listen to The Cure on loop, think again. Your 30 and 40s are the BEST time to travel with your parents – and here’s why.

I’ll get to the reasons soon, but first indulge me, please, this brief-ish history.

When I was 22 and my sister was 19, we went to Boston and New York with our parents. It was, we decided, to be our last family holiday.

As we’d got older, things had got tougher. Gone were the days of us all messing around in the pool, being bought Coke in glass bottles and mum making all our meals. As teenagers, it was all about sneaking off for tiny bottles of French beer, getting a head-rush off strong foreign cigarettes and trying to ‘mess around’ with other teenagers.

Mum still made dinner, mind.

So this US East Coast trip was to be a special occasion (indeed it was, including a fine anecdote that features the Spice Girls’ drummer) before we went our own ways: funding our own holidays, wanting to do our own thing, to travel and explore on our own terms, to buy small bottles of beer and smoke fags as and when we liked.

And this is how it worked for the next 10 years.

Things change when you get to your 30s and 40s

Then things changed.

Then my parents decided they were hiring a villa in Italy, on the Amalfi coast. They invited my sister and her husband along. And, seeing as it was quite a big villa and they thought my broken Italian might come in useful, I got invited too, with my then-girlfriend.

It was fun. A boat trip to Capri, gelati in Positano, eating in barely-findable village pizzerias, hooning around mountain roads with drops so vertiginous they almost had this atheist praying.

Then, two or three years later, my sister and her husband their first child: my first nephew and godson. Apparently, travelling with a tiny, utterly dependent human who’s likely to scream, poo or puke at any given moment, can be challenging. So my parents – now grandparents – suggested hiring another villa in Italy, this time near Rome, and taking the new family of three. Many hands and all that. Again, I was invited, along with my then-girlfriend (a different one).

Again, it was fun. The wee bairn meant taking things slower: more home cooking, more lazing by the pool, gentler walks, and restaurant meals requiring D-Day levels of planning.

Next level parental holiday

This was it for me, for a while. (My sister and her now-family-of-four have been on lots of holidays with Nanny and Gump.)

Then, in 2014, me and my then-girlfriend (a different one again, but this one is now my wife, so no more girlfriends) decided we wanted to go to South Africa. Cape Town, to be precise. We started looking at flights, Airbnb apartments, things to do – the usual.

Then, I can’t remember when, my dad said that going to the southern hemisphere was on his bucket list. I mean, how do you then say no? Plus, there were upsides. My mum loves to book a villa (as you can see), so no more searching Airbnb studios for us: Mum was on the hunt for houses with pools.

She found a four-bed house in the rather lovely Camps Bay area. This meant we had two spare rooms. My wife’s mum then mentioned that she’d always wanted to see Africa. And suddenly we were five. The romantic trip had become something entirely different.

Also, as my now-mother-in-law lives in Northern Ireland, the pre-flight rendezvous at Heathrow would be the first time she and my parents had met – and they’d be living together for a week.

But it was great. Really great. Our parents bonded, we drank the vineyards dry, ate animals we’d previously never heard of, saw the sites, jumped on tour buses, and generally made the most of the wonderful pre-Brexit exchange rate.

Keep them coming

And it didn’t stop there. There was yet another Italian villa holiday (Sicily) in 2016 to celebrate my mum’s 70th birthday and my parents’ golden wedding anniversary. There have also been long weekends in the country for mine and my sister’s 40th birthdays. This summer, we’ll be spending a week in Bunratty, Ireland, with my wife’s family, including her mum.

I’ve loved every second of these trips. If you thought your days of travelling with your folks were done, and if you’re lucky enough to have parents who are alive and capable of travel – I’d highly recommend taking a holiday or five with them.

This doesn’t mean you stop having your own holidays, your own adventures: it just means adding something different to the mix. These trips in my 30s and 40s weren’t supposed to happen, but I’m extremely happy that they did, particularly at that time in life, for a number of reasons.

Eight reasons, to be precise. Eight reasons why your 30s and 40s are the best time to travel with your parents. Here they are:

1. You’ll be more open-minded

The older people get, the less they care about doing the ‘cool’ thing or how they’re seen. You might think you’re too seasoned a traveller to do, say, a city bus tour. Your parents will see it as a really efficient way to get their bearings and learn a bit about where they’re visiting. (Cape Town has an amazing bus tour, by the way.) Now, when I travel, I couldn’t care less how touristy I look (ok, I do, but my boundaries have definitely shifted).

2. Travelling with your parents makes you try different things

No matter how adventurous we are, we all become creatures of habit. Every time I travel, for example, I search for craft beer bars and taprooms. As a couple, we’ll look for a walking tour (it helps to sweat out the hangover). That’s all great, but travelling with your folks means you might also visit a museum or gallery or restaurant that wouldn’t otherwise have been on your itinerary.

3. You do things at a different pace

Modern life is rapid. Why else would there be ‘slow’ cultural trends around the world, like slow TV and slow food? Back in the day, they would have just been ‘TV’ and ’food’. As a result, we tend to do things at 100mph – and when we go on holiday, it’s hard to slow down, at least for a few days. Your parents are of a less-frantic era. If you move over into their lane, you’ll enjoy a more relaxing trip.

4. You might learn something

Actually, you might learn some things. You might learn a few travel tricks that aren’t available via Instagram influencers or YouTube videos. You might learn more about where you’re visiting (because you’re going to different places and more slowly, see?). And, perhaps most importantly, you might learn something about your parents. Which brings me to…

5. It’s enforced parent-child quality time

What do you do when you visit your parents? Have a meal? Go for a walk? Go to the pub? Walk to the pub for a meal? Argue about politics while having a meal, walking or at the pub? Sit on your arse and watch TV? My hand is raised. I’m in my 40s and even then I still revert to the habits of my teens (I even sleep longer). On holiday, it’s different. In the same way that you don’t take your comfy slippers on holiday, you’re also less likely to slip into old routines (and you’re less likely to understand the TV). This means you have more and different conversations with your parents, which is an excellent opportunity to learn more about them: them now and them in the past. It also means…

6. You’ll have more shared experiences and these are precious

They really are. How often do you repeat the same stories over and over and over again with your friends? You recount events that you all witnessed or took part in. “Remember that time [insert probably-booze-related anecdote here].” Totally unnecessary, but totally never boring, either. How many of these events took place on holidays or weekends away? Exactly. Why not have that with your parents? More importantly, why not let them have that with you?

This Father’s Day, we asked people in their 30s and 40s to recall those childhood memories and ask themselves: What did my dad teach me about being a grown-up?

7. Your parents aren’t getting any younger

Facts can be crappy, but they are facts and sometimes we just have to stare them dead-eyed in the face, because you can’t change facts. That’s the nature of facts. It’s their thing. One of the hardest facts to face is that we’re all going to die and that your parents will probably die before you. How sh*t is that? This makes the time we share with them incredibly precious.

Ask anyone who’s lost a parent what their biggest regret is and I’d wager top of the list would be things like “I wish I’d spent more time with them” and “I wish I’d spoken to them more”. (Even writing that is going to make me call my parents later.) A holiday is a great way to do both in really intense bursts – especially handy if you don’t live near your parents.

We should all make every day a father’s day or mother’s day, but life is busy and stuff. So why not have a father’s and mother’s week or fortnight once in a while? If you’re in your 30s or 40s, chances are your parents are in their 50s, 60s or 70s – great decades for travel. Young enough to get about and have fun, old enough to have gathered much wisdom, and probably the richest they’ve been in their entire lives – which makes them do things like book luxury villas.

8. And neither are you

Yeah, of course, you’re crazy and adventurous and fun-loving and can rock it out until the sun comes up, but be honest: is ‘high octane’ quite as appealing as it was in your 20s? For a whole holiday? A holiday with your parents doesn’t mean cutting the engine – in South Africa, my wife and I climbed Table Mountain while the parents took the cable car – but it’s an excuse to bring it down a notch and smell the flowers without feeling like you’re not ‘maximising your fun’. So go on – live a little (slower).