Traveling in Your 30s and 40s Is a Different Beast from the Halcyon Days of Your 20s

When the words “decent health insurance” become music to your ears

Traveling in your early 20s is like a rite of Western privilege passage. You pack your backpack and — for better or worse — head off for months or even years of hosteling, casual sex, and drinking your body weight in bucket cocktails.

But in your thirties and forties, travel takes on a different weight.

I’m 37, travel full-time, and have noticed some rather specific age-related challenges that never plagued my 20-something backpack adventures.

If you’re traveling in your *ahem* later years, you might recognize a few of these.

When you’re 25, people don’t ask you what the heck you’re playing at

No one questions travel if you’re on the young side of a quarter century. In fact, if you don’t take your traveling rite of passage, you might be asked why not.

Hit your thirties and people’s tone changes. Gone is the go out and experience the world! message. You’ll more likely be asked are you not worried about your career / housing prospects / starting a family?

I’ll level with you — I hate the questioning. Travel isn’t an itch satisfied with one scratch in your early twenties, yet we’re expected to ignore it from our thirties onwards for more “normal” pursuits.

But as anyone with a wanderlust stronger than your local coffee shop’s triple shot espresso knows, that itch never goes away. For some, that means traveling in your thirties, forties, or even older (my father still travels and he’s in his mid-seventies).

You — as a thirty or forty-something — may have seen the light and understand there are as many ways of living as there are people, but that doesn’t mean the world has cottoned on just yet.

All you can do is get on with what you do best, suitcase in hand.

Your thirties come with a give-a-f**k attitude that serves you well when you travel

One of the best things about getting older is how much less I give a f**k about things that would have scared the crap out of my 20-something self. Back then I was both self-conscious and anxiety-ridden and I was more influenced by people around me than I cared to admit.

When you travel, this sort of attitude can do you a big disservice. You may “go with the flow” which means you may spend your money and time in ways that don’t fit with your personality or values. I spent an awful lot of money on trips to touristy places during my twenties for instance because that was what I was told I should do — even though those sorts of tours were never my thing.

Nowadays, I’m much happier doing what I want to do. For instance, in my 20s I remember desperately wanting to walk into the traditional tapas bars of Spain — the ones with old Spanish men in the corner playing cards all day long — but I was too scared.

Now, you’ll find me propping up those sorts of bars with the best of them.

There are many advantages of getting older. The give-a-f**k attitude is a big one.

You wonder what the nearest hospital is like

Back in my twenties, I shipped off for a three-month jaunt around Europe without a health care in the world. It would never have occurred to me to check what the hospital situation was like in any given town because like most healthy 20-somethings, I hardly gave it a second thought.

As I’ve aged, I’ve become much more interested in the local hospital. Is it any good? How can I access it if I need to? What’s the emergency number of the country?

It doesn’t help that I’m horribly accident-prone. So much so that my family used to claim it wasn’t a proper family vacation if I didn’t trip up at least once a day. And my stomach is more fragile than I would like, so picking up food poisoning or — as I did in Spain earlier this year — norovirus, is essentially inevitable.

Local hospitals were not exactly on my 23-year-old self’s radar. At 37? You bet I’ll be checking out their safety ratings.

There’s this new fangled thing called the internet now

Anybody born pre-1985 who traveled in their 20s will appreciate how much the internet has revolutionized travel.

When I took my traveling rite of passage back in 2007, the internet existed but to access it you’d have to head to a rip-off internet cafe. When it came to accommodation, there was no Airbnb. Instead, you were at the mercy of either a hostel aggregate or you knocked on doors. Your leisure time was dominated by what was held in the pages of a Lonely Planet guide.

It was expensive and time-consuming. You were more likely to find gold on the beach than a decent room and every activity turned out to be a tourist trap.

Now I travel in my 30s with the whole of the internet at my fingertips via a phone that costs me $10 a month, life on the road is a whole lot easier, more pleasant, personalized to my tastes, and funnily enough, cheaper. I spend less now per month than I did on that 2007 trip.

The internet is problematic in so many ways but when it comes to living abroad, it’s a freaking lifesaver.

You’re (hopefully) better at crafting deeper, more satisfying connections

Back in my 20s, I was interested in creating just two types of connections whilst traveling. One was with people like me, the backpackers, the drinking companions. The other was the romantic idea of befriending old Greek widows or Italian families who would welcome you into their homes with open arms and feed you until you burst.

The problem was, old Greek widows aren’t that interested in 23-year-old backpackers invading their homes and many people I met in hostels were, well, dicks.

Nowadays, I keep an open mind about the sort of people I meet, and the sort of connections I’ll build. I’ve realized I can’t force my own ideas of how people in a certain country should behave either towards me or towards each other (especially when all my notions came from Captain Correlli’s Mandolin).

It’s served me well. I’ve built stronger, deeper connections in much less time during travel in my 30s than I ever could have hoped for in my 20s. Anything from 25-year-old Dutch CEOs traveling the world as digital nomads, to Australian food technicians stuck by the pandemic in central Spain to Portuguese winemakers to Croatian bar owners, and more besides. Each one a new friendship, each one a connection to the places I choose to travel.

Old Italian nonnas still seem to be out of reach still, however. Time to work on the Italian before I hit Naples this November…

TLDR: Traveling older is awesome.

Sure, you have to endure questions about your life choices and you might find local healthcare becomes a Thing.

But you’re also more adept at creating long-lasting connections with the people you meet. You give less of a f**k about what people think of you which can lead to more interesting experiences. And thank Christ, unlike in your 20s, you now have the internet at your fingertips.

So go forth my middle-aged friends and travel your ass off. And let me know which age-specific challenges I’ve missed here.

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