Travelling with Less Direction

Like many of us, the anticipation of our future travels has us half crazed with a flurry of emotions, fueling us to seek out raving reviews for the very best hotspots and must-see attractions circulating around the globe, or perhaps the best watering holes and drool-worthy food. With travel comes the meticulous forethought, planning every last detail down to your seat selection—window or aisle? But there is something about spontaneity, and the way it can influence and heighten your travels tenfold.

The truth about travel is that there are ups and downs to every journey. There is no exact route to any destination, but rather guides and tips catered to each location. Whatever path you choose to follow is totally up to you, but what I hope to offer is simply an alternative perspective, perhaps a new way to travel, and to provide you with inspiration for your next journey. This I have experienced and learned firsthand through my own personal travel diaries; let’s jump in!

While travelling through Italy a couple of years ago, my friends and I were expecting to arrive in Florence for our next stop. With our backpacks loaded up (we weren’t the savvy packers we are today) and weighing us down, frustrations were at an all-time high. It must have been the third train transfer, and I was beginning to wonder where we were headed and when we would arrive. Deboarding the train at a small station in a quaint Italian town, we came to the queasy realization that we were not in fact in Florence, but in Certaldo. We seriously considered turning around and trying to make our way back to Florence, but with the on-and-off train strikes and with no desire to carry our backpacks any longer, we ended up in this beautiful Tuscan town for a few days. A little uneasy, and unsure of the hostel location, which we mistakenly booked in Certaldo not Florence, we were soon surprised by the cab driver hailing us down—apparently there was one hostel in all of Certaldo and we clearly stuck out as tourists. We were a bit hesitant, but with no one else around and no real idea of where to go, we decided to jam our bags and ourselves into the van. All locals, beside the hotel owners that is, were Italian, not knowing a word of English. And we not knowing Italian, found ourselves struggling with a bit of a language barrier in town until I thought of communicating in French—not quite the same, I know, but there were enough similarities that we could get by. Certaldo may not have had the grandeur, or notoriety of Rome or Florence, but it ended up being all the more memorable and to this day, it remains one of my favourite underrated spots in Italy. One slight wrong turn—and a booking mistake—led us here to this charming, majestic town and as we entered the one local bar called, The Bar, filled with locals enjoying an aperitif at the end of the day we sure were glad.

From the Kosan archives

It was this experience in Certaldo that inspired me to let go a little and to learn the art of planning less. Since returning from this trip, and with each holiday in between, I have heard the same unceasing questions after my travels: What did you see… where did you go… what did you buy? All appropriate and rather normal inquiries, yet for me it hasn’t really been about the monuments and landmarks I’ve seen, or the fun little trinkets I’ve brought home (okay, sometimes they do). The experience is all about the feelings that remain—the long-lasting impressions and memories that I will have forever. Day-to-day activities can get jumbled together and forgotten, while the most beautiful and impressionable memories are associated with the sentiments created in each place; a part of a new reborn spirit left behind.


From the Kosan archives

Letting go of pre-planning every little detail of our travels can be difficult, trust us, we know. However, if given the chance, it allows us to open up our minds, freeing ourselves from expectations, prejudices and curated views of sought after destinations. We are able to see the world not fixated in judgments, but rather with an unobstructed point of view, seeing it with fresh eyes. It leaves us free to take a chance, turn a wrong corner or two and discover a new pathway to the unknown. With little to no expectations, the hidden cultural treasures can unfold before us in the most magical and transformative way.

Spontaneous travel, with little planning, forces us to get out and explore, to push our limits, and to connect and interact with those around us. There are risks associated with unplanned travel, and of course, there are times when being well prepared and well researched are extremely helpful, if not necessary after all there is insight to be learned from past travelers. But trust that we too have a point of view worth exploring. There is a time and place for both perspectives, but we should try and push through our fears, break boundaries and explore outside of our comfort zone. The well-planned itinerary may look fool proof, but until we set foot on foreign grounds, we may never know what we missed by sticking to a schedule, scouting out tourist attractions. There is some value in wandering the streets, and stepping off the beaten path—fewer lineups too.

So with some curiosity left in your step, just get up and go! Let’s plan less, have fewer expectations and spark some spontaneity!

 From the Kosan archives


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