How a summer in Italy helped me rediscover the joy of spontaneity

There I was, on the rooftop of a building in Naples, furiously scrolling through a Google search result. My partner had just told me that he read somewhere that Capri had closed its entry to tourists who do not hold a hotel reservation, due to a cracked water pipe resulting in a water shortage on the popular island.

He said it so casually, before continuing to sip on his prosecco. Meanwhile, mouth agape and mind racing at a million miles per hour, I ignored my freshly set-out plate of pasta trying to find anything that might indicate otherwise.

You see, the morning after, we were scheduled to take a ferry over to the island. Having never been to Italy before, let alone Capri, I had only the impressions of the island that was gleaned from the media and from TikTok. Sophia Loren in a bodacious dress, set against the blue skies. Jennie walking for Jacquemus’ runway show. Dua Lipa tucking into a gelato as the coastal winds blew in her hair.

You see, the morning after, we were scheduled to take a ferry over to the island. Having never been to Italy before, let alone Capri, I had only the impressions of the island that was gleaned from the media and from TikTok. Sophia Loren in a bodacious dress, set against the blue skies. Jennie walking for Jacquemus’ runway show. Dua Lipa tucking into a gelato as the coastal winds blew in her hair.

And here’s a second thing you should know about me: I’m a traveller who likes things in place. Ask any of my friends, they’ll attest to this. I’m meticulous in ensuring there is a shared calendar with the itinerary mapped out. Every restaurant we plan to visit has a standing reservation. Every attraction that allows for advance ticketing would’ve been paid for, and the PDF would be saved in a shared folder.

I’d have care packs ready at the start of the trip filled with travel essentials—effervescent tablets, hand sanitisers, hand fans, basically the works—and every route is meticulously mapped to minimise transit times and ensure that we are making the most out of our time.

Yes, I am a Type A traveller. It may not work for everyone, but hey, anytime someone needs a wet wipe or an extra USB wire, I’ve got that covered.

Boat to where?

So back in Naples, there I was, coming to realise that I had to overhaul the entire plan of spending our anniversary in Capri. There goes the beach club reservations, the boat tour to visit the island’s grottoes, and so on. Not to mention, what are we going to do tomorrow?

If anything, Italy was a real test of letting go. I wasn’t prepared by any means for this life lesson, but I was glad to have it nonetheless. We know that Italians have perfected the art of going with the flow, of celebrating the “dolce far niente”, which translates to the “sweetness of doing nothing”.

Yet for a true-blue Singaporean who’s used to the bustle and adrenaline of city life, ‘doing nothing’ is a foreign concept. We’re taught that to do nothing is to waste time, and idleness equals to nothing good, duh.

Post-dinner and still without a plan, I found myself at the counter of the hotel, trying to see if the concierge could reverse the ‘no tourist’ ruling. Spoiler alert: he could not. But what he said next was, in hindsight, a gift. In a nonchalant tone, he told this writer, “The Amalfi Coast has so many other beautiful islands. You can try to search for another place to visit.”

Now, you may think that this is a pretty obvious reaction. “Plans change, so put on your big-boy pants and just deal with it,” you might be thinking about me. And in truth, you’re not wrong. But when you’re so fixated on controlling the trip, these things often evade common sense.

A quick Google search yielded “Procida” as a potential substitute. One travel website dubbed it the “Little Capri”, and that was enough to convince me. I quickly had tickets for the morning ferry booked, but aside from that, I had nothing else planned.

What a relief that I left it all up to the fortunes of the travel gods. While most tourists flocked to other parts of the Amalfi Coast, I found myself on the way to Procida, an island more popular with Italians than with tourists.

“Where to now?” my partner asked as we disembarked.

“Don’t know, let’s just walk and see,” I replied.

And see we did. On a small street, I chanced upon an old lady who was making brass jewellery by hand. Without speaking a word of English, she beckoned me to take a look. Through hand signs and “ah, uh” muttered in between smiles, I bought a handful of pieces for friends.

We later found ourselves hungry and looking for a lunch spot. “Here we go, “ I thought, “Let’s see where we land if we turn right up ahead.”

We eventually found ourselves at a quaint cliffside restaurant named La Lampara, where we had an incredible burrata dish, except instead of the usual tomato and basil pairing, our ball of cheese came sliced and stuffed with pickled sardines. It was deliciously umami and a fabulous find made possible by taking a random turn down a random street. We spent the rest of the day napping and reading on a beach favoured by the locals, before taking a ferry back to Naples for dinner.

On and on, Italy proved to me that there is so much beauty in the spontaneous.

Spontaneous swims in Sorrento

After a tour ended unexpectedly early, we found ourselves with nothing to do. So instead of fretting, we got into our rented Fiat, and started driving down the coastal highway and taking many stops to snap plenty of pictures for the ‘gram.

Eventually we found ourselves in Sorrento, a Kodak-worthy spot on the coast. Enamoured by the view of Mount Vesuvius overlooking the sapphire seas, we decided that this was where we were going to spend the rest of the day. We ate lobsters caught from the sea that morning, found a small sundries store where we bought all the supplies we needed—swimming shorts, slippers, sunscreen, and potato chips—before finding a spot on the beach. A guy came over with a brochure for a sunset boat ride, and rather than wave him away like all the other beachgoers, I said “yes”.

It was the best $200 I spent. While the boat tour wasn’t a private session, we were the only ones to read his brochure, and the only ones to board his boat. What would’ve set me back $500 for a private ride up and down the coast, only cost less than half because I let go of the reins and let life plan for me. We had prosecco as the sun set, we swam in the vicinity of Roman ruins, we watched the sun set on a beautiful day.

On another occasion, we had taken the wrong bus in Rome and ended up in an area too far away from our intended destination. Rather than panic, we just strolled around, and found plenty of historical vignettes in the small alleyways and streets that we totally forgot about missing our stop.

In retrospect, maybe this is the beauty of travel. You can plan everything right down to the miniscule details, to each second, to every minute action, and yet, fate may have something else planned for you.

Life happens. Accidents, cancellations, diversions are all part of life, and when you travel with a watertight itinerary, you leave little chance for life to surprise you and strike you with the joyful awe you’d normally experience if you left the beaten road and found nirvana.

Will I still be planning trips for the friend group? Yes. But will I now leave windows for life to lead us? Definitely.

This article was originally published in Harper’s Bazaar Singapore.