The Best Laid Plans

Spontaneity or schedule?

Hello and welcome to the 61st issue of Place! In today’s dispatch, our editors are again talking two different sides of the same issue. This week’s debate? To plan or not to plan when going on a trip. Is spontaneity, while being a romantic choice, really the most humble way to approach a new place? Is planning, on the other hand, the best way to meet a place where it’s at? It’s a conversation we’ve likely all had to some extent -- which side of the line do you fall on? Read what our editors have to say, and then let us know what you think in the comments below! 

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At Place, we believe that the experiences, sensations and conversations we have as we move about the world stay with us, stacking up as the years go by, forming who we are and the way we view the world. Do you have a letter to share? Send it to us at If you are interested in writing for Place you can find our pitch guide here. If you’re the social type, follow us on Twitter (@place_letter) where you can share your favourite pieces and Instagram (@placenewsletter) for a visual feast. Yours, The Place editorial team.

Dorset, home of England’s Jurassic Coast, can seem a bit of a forgotten strip of coastline. Around two-and-a-half hours traffic-packed drive from London, it is neither close enough for an ice cream and clams day trip nor seemingly worth a stop on a long haul drive when the breathtaking cliffs of Devon and Cornwall are just beyond its western borders. 

Though I was intrigued by the striking photos of Durdle Door, an enormous sloping stone arch stepping out into the sea,I found myself pulled to the dramatic mountains of the Lake District and surfable Welsh coast when it came to exploring the UK over the last year.

However, a photo of climbers scaling limestone cliffs over a coastal vista on the Isle of Portland on the Dorset coast piqued my interest. A bank holiday was ahead and my friends were all itching to get out of town. Then, a last minute cottage nestled in rolling farmland, heated with a wood-burning stove and decorated with self-portraits and spray paint art, popped up on Airbnb. We decided to book. 

So I got to planning.

I’ve always been a planner, albeit slightly in secret. As soon as the tickets are booked, I start dropping pins on a private Google Maps, adding to a password protected word document of potential itineraries, and building a budget spreadsheet. Planning my trips is a vital part of the traveling experience - I start to imagine myself rounding a cobblestone corner in Tbilisi and stepping into a vine-clad wine bar or pushing the curtain to enter a tiny bar for yakitori in Tokyo. These places become destinations I dream of, stepping into them is like meeting that dream in reality. 

I once planned a trip to Modena, Italy, specifically to visit a Parmesan-Reggiano factory that had been nearly destroyed in an earthquake. To aid in the recovery, a Michelin-starred chef reworked the classic cacio e pepe recipe to feature the region’s nutty cheese, resulting in the sale of 360,000 wheels, saving the local industry. I watched as the curd churned in massive metal vats, was scooped up in basketball sized pouches of cheesecloth, packed into wax wheels to age, stacked meters high in an enormous warehouse. When I tasted the 24-month aged Parmesan, thinking of the time and effort it took for this taste to arrive in my mouth, I shed a little tear. 

Plans can work.

However, planning has gotten a bit of a bad name in the YOLO-era of travel, where spontaneity seems to be the only acceptable route to an authentic travel story. If you can book it in advance, is it really experiencing a place? Or is it just placing an order on a menu of experiences? I hide my plans to make it seem like I just guessed there was a scenic route off the main highway or came across a cafe on a recommendation from somewhere cooler than Google. I wonder what I miss between the dots I have saved on my map. At times, it doesn’t feel like the right way to travel.

But perhaps the time has come to unveil myself. To me, planning and research can be an act of respect toward the destination. It means coming into a place without the arrogance of believing it will serve you a smorgasbord of stories, but rather a living, breathing ecosystem of people and built environment that has existed long before you visited and will continue on well after. Traveling is about joining in lockstep, not crashing the parade. A plan allows you to understand what a place of proud of, and to understand its context. And in a way, I think it can also be about understanding oneself. Is it that you don’t want to plan or that you don’t know what you want to do?

By the time we arrived in Dorset, I had my plans in hand. We trudged through a classic afternoon English spring downpour on our way to a rocky beach, but I knew it would be worth it to soldier on. When the sun returned, we ended up spending hours admiring spirals of ancient ammonites fossilised in the limestone boulders. On the Isle of Portland, my hours pouring over the bouldering guides in the region led us on a tiny path next to the crumbling ruins of a 11th century church to a quiet cove for an icy dip, and then on to the bouldering fields along the coast nearby. 

That doesn’t mean there weren’t plenty of pleasant surprises and last minute decisions along the way. But the plan ensured that I would not forget about Dorset again.

  • Karis Hustad is the co-editor of Place and a journalist based in London, UK, who covered debt until today. Soon, she will write for a magazine.

I’d been in India for two months, and at this point, was beginning to realise that whatever plans I had for being somewhere on time, or moving at the pace of our preplanned schedule were not ambitions I was readily going to be able to pull off. 

The getting-to-places-on-time aspect was not so disheartening, as I had no appointments to make or people to meet as a foreign traveller. When I did miss a bus or a train, another always seemed to appear. At times, uncannily. That said, I had roughly mapped out some of the places I wanted to visit before my trip started, and treated each point like a marker in time. By March, I’d be in Varanasi. By May, Sikkim. 

I did not make it to Varanasi by March. 

Instead, I was still in the quiet (at that time of year) town of Pokhara in Rajasthan, with the two friends I was travelling with, planning out the couple weeks ahead by drawing messy calendars in our journals. I remember sitting on pillows near the lake, which our guest house backed on to, dodging monkeys and stuffing mango into our mouths, the stickiness of our fingers leaving smudges on the paper we were pouring over. One of us, I can’t remember who, declared we had to cut out a side-trip to a certain city, and take the overnight train to make it to Varanasi to have enough days to explore the place. Black x’s were solemnly drawn, and, like that, a choice had been made. 

Who knows what we missed by not going to that city we cut out, that I now forget the name of. Who knows what we gained by those extra days in Varanasi? Would I have had as many mosquito bites on my ankles? Would we have been able to do that sunrise boat ride on the Ganges, the soft sounds of seagulls wings and the splashing of laundry in water lingering as long as the smell of marigolds in the early morning air?

With all of the resources at our fingertips for trip-planning, the process can often be overwhelming. There are only so many lists of ‘must-see’ places that one can read before starting to feel as though there won’t be enough time to even scratch the surface, let alone really get to know a place. Maybe part of my aversion to planning is the awareness of this - that no matter how much scheduling I do, I’ll never be able to do it all. 

Planning, even in its best form, often seems to me a half-hearted exercise - cut down at least by the fact that we never know, as travellers and as general beings making choices in the world, what we are missing when we choose one place, event, or excursion over another. This pre-supposed loss is even more abstracted when it's a place we’ve never been to anyways… we have no experience to refer back to, no precious memory to relive or remake. We only have a promise of what ‘could have been’ - a focus perhaps on everything we missed, rather than whatever it was we actually saw. 

It’s cliche to say that the best moments of a trip are the things that you never planned, or the moments you never expected, but I think I can safely say that it still rings true for me. I think that maybe that's because those moments have no expectation attached to them -- they aren’t built up in your mind as a daydream waiting to be fulfilled, and therefore, they can never fall short. Instead, they teach you about a side of a place you never could have pre-supposed, a side that feels even more intimate because you didn’t read it on a travel blog or find it in a guidebook. It came to you, unwritten and ordinary. 

Looking back, I’m sure whatever plans we made during that months-long trip to India changed myriad times. I can’t remember the have-nots, or the things we left at the wayside. The only thing I’m left with now are the rich memories of ever-unwinding days, moulded from moments of decision making spurred on at times by a spirit of adventure, and at other times by exhaustion. Mostly though, I think they were decisions made with a certain degree of freedom -- that whatever we happened upon would be more than enough. We were just lucky to be there. 

  • Kylee Pedersen is a co-editor of Place and a writer based in London, UK. She writes about travel, food, and the natural world, among other things.

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Join us next week for a new journey.