I Stopped Treating My Travel Itinerary Like a To-Do List. Here’s How It Transformed My Holidays 

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There’s a stage of planning a trip that I imagine many of you will recognise. It starts with browsing travel blogs, looking up things to do in a particular destination, and making a list of places worth visiting and experiences worth having. Before long, there’s more than enough to fill the days. A popular museum or gallery, a viewpoint, a walk through the old town.

All perfectly good choices.

But the more I travelled, the more I noticed a certain repetition in my itineraries. Not because the destinations themselves were so similar, but because I kept approaching each new place in much the same way.

I was so concerned with not missing out on anything “worth seeing or doing” that I rarely stopped to ask whether any of it truly interested me. And somewhere along the way, I began to wonder whether, in trying to experience everything a place had to offer, I was leaving too little room for experiences I might discover on my own.

Given an afternoon with no recommendations and nowhere in particular to be, where would my curiosity take me?

For instance, there is this fun event that happens in Edinburgh once a year. Called Art Walk Weekends and held in the neighbourhood of Portobello, right by the sea, it encourages local artists and makers to open up their homes, studios, and workshops to strangers. In other words, as a visitor, you get permission to do something you might otherwise feel a little awkward about: walk into a stranger’s house, have a good look around, and ask someone what they’re making.

And because many of these places are the artists’ homes, you get to indulge that very human urge to see how other people live. You came for the paintings, of course. But you might also leave with an idea for your kitchen and a question about where the owner got those shelves.

I’m not much of an art connoisseur myself, and constantly pushing myself to visit museums and galleries wherever I travelled only made me appreciate them less. But when I carved out time for this Portobello art walk, I found myself in the company of other wanderers, making small talk and enjoying unplanned, undemanding moments of socialising. On many occasions, I also found myself chatting with artists, either learning about their creative process or asking equally pressing questions about the shade of paint on their walls or the scent of the candles in their living rooms. And with dozens of artists participating, I also discovered art that spoke to me and felt a connection to it.

The reality is, however, that Portobello and its art walk are often overlooked in favour of Edinburgh’s headline attractions. Which is a shame. Right by the sea, historic and scenic, Portobello shows a very different side of the Scottish capital. And the art walk captures the spirit of its community: friendly, welcoming, and endlessly creative. I’m not about to pit Porty against the Royal Mile, though, or devise yet another ranking of places you should see and places you can skip.

Editor’s note: Planning a trip to Edinburgh? Seriously, don’t miss out on Portobello! Give it a go with a mindful swimming session at Porty Beach or join an e-bike tour along the coast. It’s a lovely way to experience a different side of the city.

What I’m inviting us travellers to do is leave a little room for curiosity when we plan our trips. Keep the museum booking, but perhaps leave the afternoon open for something you haven’t experienced before. Give yourself the chance and the permission to follow an interest you didn’t think belonged on your itinerary. You might learn something about a place, or about yourself, for that matter. And if all you come away with is a lovely conversation and the name of a paint colour, I’d say that counts as an afternoon well spent.

Zooming in on a curious spot on a map of Slovenia led me to a fascinating lake I’d never seen mentioned in travel blogs.

A Holiday From the Person You Usually Are

When I first started thinking about what holds us back from giving in to our curiosity and allowing it to shape our travels, I came across one study. Conducted by the British Heart Foundation, it explored comfort zones and daily routines, revealing that about 55% of Brits stick to their daily routines day in, day out, while around 31% struggle to remember the last time they ventured outside their comfort zones.

This is the point where I must say that it is not my intention to put Brits on the spot. In fact, when I dug deeper into surveys from other countries, I found that this reluctance to embrace unfamiliar experiences in everyday life is not uniquely British.

And those numbers alone, I would argue, can be interpreted fairly neutrally. However, the researchers also asked whether respondents worried they might one day regret not exploring beyond their comfort zones. And 45% admitted that this was indeed one of their fears.

Above all, this research shows just how beautifully human and vulnerable we are. Because on the other side of predictability and routine — structures we’ve carefully built to protect ourselves from the very real pressures and demands of our personal and professional lives — lies uncertainty. The opposite of comfort is challenge. And guess what stands in opposition to knowing what to expect? Curiosity. 

Not necessarily the type of curiosity that almost shames us into abandoning our carefully constructed comfort zones and venturing into the unknown on a whim. But the one that gently exposes us to the joy of discovery. Reminds us what it feels like to be alive and engaged. Builds our tolerance for uncertainty. 

And better still, it allows us to discover more about ourselves. There are so many different sides to each of us. But within the safety of our daily routines, we often end up nurturing only a small part of who we are: professionals in our fields. Parents. Partners. Singles. The rest of who we are remains unexplored, unexpressed, or neglected for most of the year.

As I’m writing this, I remember a conversation with a woman I met on one of the small beaches in Sri Lanka. Far from the popular surfing spots but close to a couple of villages, the place looked every bit like the tropical paradise advertised on TV. And just as secluded.

So when I bumped into the only other person there one morning, naturally, we got to talking.

She told me this was her first-ever solo trip. Working on the tills at Tesco, she’d had to save up for quite a while to afford the journey. And then there was her family, whom she’d had to convince that this was one holiday they wouldn’t be tagging along on.

And boy, was she making the most of it. “I honestly don’t recognise myself!” she said, half elated, half stunned. In the short time she’d been in Sri Lanka, she had struck up quite a few friendships with locals, leading to invitations for tea and a bit of local banter. She had taken dance classes and made it her mission to try as many new foods as she could. She slept for as long as she wanted and even went so far as to leave her phone behind on her daily explorations of the area — curious to find her way around without relying on GPS and unbothered by the thought of missing messages or calls from the folks back home.

“I must figure out how to hold on to this version of myself when I go back home!” she concluded. And she is not alone in that sentiment. According to one survey, as many as 68% of people wish they could be more like their holiday selves in everyday life. 

And I wonder how much of that has to do with giving ourselves permission to be curious.

Because, at its heart, curiosity is an opportunity to learn. But since travel is leisure, we get to trick our brains into thinking we’re not doing the heavy lifting often associated with learning. So we get to combine the best of both worlds — explore our wants and likes a little further, all while discovering a bit of the world beyond well-trodden paths and predictable routes. And all of this while we’re on holiday.

I love chatting with strangers when I travel, and one conversation with a gift shop owner in Pittenweem led me to a hand-painted wall by the village’s tidal pool.

How to Plan for the Unplanned

So how do we leave room for curiosity without turning it into yet another item on our to-do lists?

One thing I’ve found helpful is to learn a little about the traditions of the place I’m visiting. Every country has its own unique culture, rituals and landscapes. And the easiest way to get a feel for what makes a place distinctive is by becoming just a bit nosy about the people who live there. What do they actually enjoy doing? Local festivals, hiking weekends, wild swimming, art walks, poetry readings — even a tiny lead can open up a whole world of unexpected experiences.

Another good way to make room for curiosity in a travel itinerary is to prioritise personal interests, especially those that rarely get much attention in everyday life. 

A long-standing interest in painting, for example, might inspire a trip to a destination known for its artistic traditions. A love of music might lead to discovering a local festival or planning a visit around a particular performance. An avid knitter in my spare time, I dream of building one of my trips around exploring the stages of wool production before those skeins reach the shop shelves. I’m sure the rest of the itinerary will take shape around that initial interest.

And I’ve lost count of the times I’ve found something interesting simply by zooming in on random corners of Google Maps, tapping on places that caught my eye and reading reviews. This curious scrolling has led me to a beautiful, uncrowded lake in Slovenia, a stunning hike in Scotland and a café in Menton with excellent breakfasts and the friendliest owner’s dog in the world, to name just a few.

A Little Inspiration for the Curious Travellers

I thought I’d leave you with a little inspiration. Across Europe, there are events that offer a glimpse into the wonderfully unexpected things people create, celebrate and come together for. Here are five that might just spark your curiosity — and perhaps even inspire a trip you wouldn’t otherwise have thought of taking.

The Fringe Festival in Edinburgh, Scotland

A behemoth of an event, truly. The Fringe is marketed as a festival, but that hardly seems like the right word. In fact, as many as six festivals take place in the Scottish capital during August. There’s the Fringe itself, the world’s largest open-access arts festival, with thousands of free and paid shows. Performances happen on the streets, in pubs, theatres, churches and some very unlikely venues. Pretty much anywhere a performer manages to find and book.

Then there’s the Edinburgh International Festival, a more refined affair, with a carefully curated programme of theatre, opera, classical music and dance, featuring world-class performers in some of the city’s grandest venues. The Royal Edinburgh Military Tattoo, with its spectacular displays of military bands and pipers, takes place on a purpose-built stage on the esplanade of Edinburgh Castle. And you’ll also get a chance to explore the Edinburgh Art Festival, the Edinburgh International Book Festival and the Edinburgh International Film Festival.

All I can add is this: if you decide to go, start booking accommodation for August at least six months in advance. I also have a free guide to solo travel in Edinburgh in case you need some help.

Anything Red Bull-Curated

Sometimes exploring curiosity involves building a flying bathtub, racing downhill in a homemade contraption or jumping off a cliff. Red Bull has made something of a speciality out of celebrating human ingenuity and the occasional spectacular failure. 

At the Red Bull Flugtag, teams attempt to fly their wonderfully ridiculous, homemade aircraft over water, usually with rather predictable results. The Red Bull Soapbox Race puts creativity on wheels, challenging teams to race their eccentric, engine-free creations downhill. And for those who prefer their thrills with a little more precision, the Red Bull Cliff Diving World Series sees professional athletes perform breathtaking acrobatics from heights of up to 27 metres. 

Whether you fancy joining in or watching from a safe distance, there’s plenty here to feed your curiosity. The events take place at different locations around the world, including Europe, and not all return to the same cities or dates each year. Which makes planning a trip around one a little less predictable, but arguably all the more fun.

Fête des Lumières, Lyon, France

Every December, Lyon in France turns into an enormous canvas for the Fête des Lumières, or Festival of Lights. For four nights, artists transform the city’s buildings, streets and squares with spectacular light installations, projections and visual illusions.

The tradition dates back to 1852, when the people of Lyon placed candles in their windows to celebrate the unveiling of a statue of the Virgin Mary. To this day, residents continue to light small candles, known as lumignons, on 8 December, keeping the original spirit of the celebration alive.

As a traveller, it would be fun to explore Lyon during the day and then see how completely different it looks at night. And with Lyon being Lyon, there are endless possibilities for good food, things to do and day trips to take in between.

Festival della Mente, Sarzana, Italy

A festival dedicated entirely to the human mind? Apparently, that’s a thing. Every year, the small Italian town of Sarzana hosts Festival della Mente, bringing together writers, scientists, philosophers and artists to explore how we think, imagine and come up with ideas. Expect talks, workshops and performances on everything from creativity to the mysteries of the human brain.

And if travelling all the way to Italy for a festival about thinking seems a little excessive, there’s plenty more to tempt you. Sarzana sits in eastern Liguria, just a short distance from the colourful villages of Cinque Terre, the seaside towns of Lerici and Tellaro, and the marble quarries of Carrara all within easy reach. So you could spend a morning pondering the mysteries of the human mind and the afternoon swimming in the Mediterranean or exploring a medieval village. Not a bad combination, I’d say.

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