Why I – a 20-something man – chose to go on holiday with a group of middle-aged women

I’m not alone in being young but unimpressed by holidays tethered to a bar stool and a sun lounger - Mark Curelop
I’m not alone in being young but unimpressed by holidays tethered to a bar stool and a sun lounger - Mark Curelop

“Won’t you get bored?”

This was the first question I received every time I told people about my holiday plans. My friends, my colleagues, my parents... no one could quite believe that I, a chap in my 20s, would ever wish to spend a week listening to lectures in a hotel library with a bunch of middle-aged folk – most of them women. Not only that, but these lectures were hardly targeted at your typical young male. The theme would be the role of women in Greek mythology. The Inbetweeners Movie it was not.

Alright, so there were more obvious plus points. The digs, Minos Beach Art Hotel, in the town of Agios Nikolaos on the East Coast of Crete, promised villas with private pools, modern art installations galore, the Mediterranean lapping at my doorstep and stunning mountain vistas.

There’d be plenty to do beyond the hotel too. My tour operator, Travelgems, had arranged guided trips to the palace of Knossos – fabled home of the Minotaur – and the eerie former leper island of Spinalonga. I’d also be feasting on authentic local delicacies when I wasn’t enjoying the insights of the tour’s headline act, Natalie Haynes, a classicist, author and Radio 4 presenter.

People are asking a lot more of their holidays nowadays, says Jack Rear
People are asking a lot more of their holidays nowadays, says Jack Rear

Still, a themed retreat? In my 20s? With a group who were, on average, 30 years older than me? Perhaps you can see why people thought I’d be bored on my “old people’s holiday”.

But this wouldn’t be my first. Having tried a few of the traditional holidays you’re “supposed” to have in your 20s, I’ve discovered they aren’t for me. Boozy beach breaks don’t equal rest and relaxation – I like doing things, learning, seeing sights, and meeting people. Isn’t that the whole point of travelling?

In 2019 I attended another of Travelgems’ retreats, that time in Western Greece, because the key speaker was Madeline Miller, my favourite author. It’s hard to say this without sounding mawkish, but it was a life-changing experience. Not only did I learn a lot, but I met fascinating people who expanded my horizons and came back a changed person: calmer, more thoughtful, more open to new experiences.

I’m not alone in being young but unimpressed by holidays tethered to a bar stool and a sun lounger: a 2020 study by Hotels.com found that 42 per cent of millennials are turning to retreats that offer educational and wellbeing itineraries, and travel firms have conjured up various names for the growing genre, such as “experiential travel” and “edutourism”. Whether social media is to blame, or environmentalists telling us to take only one overseas trip per year, people are asking a lot more of their holidays nowadays. Simply “getting away from it all” is no longer sufficient.

I still had jitters on my first night, however – suddenly self-conscious about my place in this group. Within this highly international bunch were retired university lecturers, TV script writers, therapists, and even an expert on restoring historic buildings. And while I wasn’t the only other man, the ladies outnumbered us five to one.

Jack's group included retired university lecturers, TV script writers, therapists, IT experts, and even an expert on restoring historic buildings
Jack's group included retired university lecturers, TV script writers, therapists, IT experts, and even an expert on restoring historic buildings

But a wonderful thing happened when our retreat leader Niki Smirni, the indomitable Athenian who founded Travelgems, asked us to introduce ourselves – everyone had the same, simple answer: because of our abiding love of Ancient Greece and its mythology. Some had arrived clutching their copies of Natalie Haynes’ latest book, Stoneblind – a feminist retelling of the Medusa story – while others were just exciting at the prospect of a week spent talking about Hera and Aphrodite. Any differences between us were instantly forgotten, and we were soon keenly debating our favourite myths and heroes. If that makes it all sound immensely nerdy, well, uh… it was.

For Smirni, forming connections is the very foundation of her business. “I see people from different backgrounds and countries who have the same interests and the same needs because they’re united by a shared passion,” she explained at dinner that night. “Travel is uniquely capable of bringing people from all walks of life together. You’re already outside of your comfort zone and in a space where you are open to learning, discovering, and meeting new people. Through this experience, we come to the realisation that no matter where we come from or what our story may be, we all have similar needs in life.”

It really works too. On my last retreat in Crete I found myself forming fast friendships with a group composed of mostly mid-life women who readily adopted me into their circle. They were passionate, funny, and wise – the types of people who I’d never have encountered in my normal social circle and yet who in this foreign land I couldn’t help but warm to.

I’ve stayed in touch with a lot of them, and when I spent the Covid lockdowns working on a novel – emboldened by the writing course we’d all attended – it was their advice, inspiration, and guidance which sustained me.

' Surrounded by these people who’d been shaped by a common interest, I was presented with models of how to grow up, how to behave, how to live,' says Rear
' Surrounded by these people who’d been shaped by a common interest, I was presented with models of how to grow up, how to behave, how to live,' says Rear

So it went with this retreat. At Knossos, we discussed the link between the minotaurs and vulvas (the site’s most famous frieze apparently depicts just that). By the sea, we listened to Haynes talk about Medea and what might move a woman to kill her children. I chatted with the classicist about “archeo-gaming” (using video-games to explore the ancient world), shared stories about Heracles while treading water in the sea with a couple from Australia, and got a little bit misty-eyed when our guide talked to us about the lives of the lepers on Spinalonga which she described as merely “yesterday” in the context of history. At dinners we talked about mythology, but more too: our careers, our relationships, our families and friends.

“We are our words,” said one of our guides, local historian Ioanna Glypti, as she finished her tour of Knossos. “Buildings and numbers tell us facts, but what matters are the jokes we share, the memories made together, the words we whisper to loved ones, the way we say goodbye.”

How often do you get to do those things with strangers? To learn about their lives and their views? It struck me often how valuable the experience was in that regard. Surrounded by these people who’d been shaped by a common interest, I was presented with models of how to grow up, how to behave, how to live. It’s different to spend time socially and as an equal with people of another generation than it is to chat to a parent or boss, and to do so in a foreign land where the social divisions between us were at their weakest was a powerful experience.

Boring? Absolutely not. I’ve returned from my “old people’s holiday” feeling like my horizons have been broadened like never before, like I have found a community and gained new friends and returned a better, wiser, more experienced person. You rarely find that by a pool on the Costa del Sol.

How to book it

Travelgems’ 2023 retreats will cover a variety of themes including philosophy, culture, nature, yoga, dancing, pilates, fitness, spirituality and mental health. Retreats take place across Europe with venues confirmed in Tuscany, Switzerland and Crete, plus more to be announced. Prices range between €2,400 and €4,980 per person for a 6-10 day retreat, inclusive of accommodation, activities, talks, and food – but not flights.

When on holiday, do you enjoy lying by the beach or do you prefer to sight-see and explore? Join the conversation in the comments section below