I’m a travel optimizer. Italy’s chaos changed all that | Canada Voices

I have a scarcity mindset about travel – there’s never enough time off – so my vacations are voracious. I thoroughly research each destination, plot efficient routes, buy advance tickets to tourist sites and make reservations at the best restaurants to pack my maximalist Google Doc itineraries with 20,000-step days. Why risk wasting a minute of my one wild and precious trip in a line-up, or scrambling for plans on my phone?

In June, I found myself in Italy. Not ideal, in its high-season timing, but that was not negotiable – friends were getting married outside the town of Avola, in southeastern Sicily – so my wife and I decided to extend our trip and head north through Naples, Bologna, Florence and Rome.

It was also not ideal because, as I learned, if man plans, Italy laughs.

Discover the Tuscan seaside resort beloved by Italy’s upper class

Unbothered by such constructs as time and space, Italian trains come and go at their leisure, sometimes switching gates minutes before departure with no notice. It’s easy to get lost, especially when signs and locals will confidently give you wrong information. Store hours are merely aspirational, restaurant servers take a relaxed approach (or, less charitably, sometimes straight-up forget about you) and orderly queues are the stuff of ancient Roman myth. Our Sicilian boat tour’s itinerary was even hijacked by two brassy older Italian women – who, at one point, just started driving the boat.

In Sicily, they call this live-and-let-live attitude futtitinni. I just call it annoying.

Europe’s June heatwave, which pulled sweat from my pores in fat beads as soon as I stepped outside, made plans even tougher. In Florence, surrounded by effortlessly beautiful and besuited men who were in town for the Pitti Uomo menswear-trade-show-slash-peacocking-opportunity, I wilted into a rumpled puddle of linen, nearly getting sunstroke on the lone evening I wore a sport coat in the name of capital-F Fashion. Italy’s chaos and climes can waylay best-laid plans, to my simmering resentment.

But something shifted in Siracusa. We arrived there in the morning, with no plans until we had to board our sleeper train to the mainland that evening. I should’ve wanted to squeeze all I could from the historic Sicilian city and its enchanting alley-carved island of Ortigia.

Maybe our first leg of the trip, when we did little more than luxuriate on Avola’s surprisingly uncrowded beaches, led to my spontaneous tolerance for, well, spontaneity. But in Siracusa, I found myself oddly content to just wander.

I had mediocre granita, Sicily’s signature icy dessert, at a bar with the fluorescent, melamine charm of an old mall, just because it had a clean bathroom. We stumbled into Ortigia’s free and charmingly ramshackle maritime museum. We discovered a rocky beach down a rugged staircase, and killed a few hours swimming and drinking ice-cold beers that we happily paid too much for. Despite my suspicions that an Ortigia restaurant named “Ortigia Restaurant” might be a tourist trap, its pistachio-prawn pasta wound up being one of the trip’s best meals.

By the time we got to Florence, we even started going back to our air-conditioned hotel for midday showers and siestas. While I initially justified them as being in service of recovery (to allow for more activity!), I began to look forward to these two-hour breaks almost as much as my plans, and to relish the simple pleasures of changing into clean clothes unruined by my flooded body.

I slashed my ambitions, trimming cute shops and snack stops from my Google Doc. Our tired bodies thrilled when we cancelled a fancier dinner reservation on the other side of Florence in favour of crispy panini while seated on the curb of a nearby piazza. I even broke my lifelong rule of never going to the same restaurant twice on vacation– I’m too tantalized by the perpetual possibility of something better – after a riotous meal at Vini e Vecchi Sapori, a family-run Tuscan osteria governed by Madonna-obsessed Tommaso Mazzanti, a genius of the craft of hospitality.

Travel is about escape, but no destination can let us escape who we are. Who we are on vacation is just who we are in the world. For me, I know my optimizing instincts stem from an unquenchable desire for control, and a fatalistic desperation to make every trip the trip of a lifetime because I cannot assume I’ll ever be back.

I’ve spent the last year or so grappling with grief, too, working to accept that control is impossible, so we should live lightly with our short time on Earth – futtitinni, in so many words. So maximizing felt good in the planning. But letting go, at least a bit, felt just as good.

The poet Ralph Waldo Emerson also learned this when he visited Italy, dreaming of becoming a different person by becoming “intoxicated with beauty.” But, he wrote, “I pack my trunk, embrace my friends, embark on the sea, and at last wake up in Naples, and there beside me is the stern fact, the sad self, unrelenting, identical, that I fled from.” Better to try to accept this – that “nothing can bring you peace but yourself,” as Emerson ultimately declared – than to pretend that you’re able to paper things over with, say, stuffed itineraries.

On that day in Siracusa, when we left Sicily for the mainland, I starrily suggested stopping for one last spritz before our train left in an hour. Spontaneity, and all that. But my wife, bless her, is wise to Italy’s little games, and insisted on sticking to the plan and getting to the station – where we found out that our train was set to depart a full 45 minutes early.

When we asked a steward about it, he shrugged and said they’d sent an e-mail (of course, they had not). Then he showed us to our cabin – the wrong one, we learned, when we were awoken at 1 a.m. by people trying to barge in.

Turns out sometimes, man doesn’t plan – and Italy still laughs.

If you go

In Rome, the heat was particularly punishing, so it was with dizzy joy that I discovered the city’s water fountains, or nasoni, named after the nose-like faucets that dispense ice-cold water in a perpetual flow. If you forget to bring a water bottle (don’t!), you can press your hand under the spout to propel the water up through a hole on top of the “nose,” in a lovely bit of century-old design ingenuity.

Say no to guided tours and look for a tourist site’s official website. It’s often borderline unusable, but figuring it out to book tickets there a month or more before your trip is an especially good idea in Italy. With official tickets and free audio guides online, you can save money and get a better experience at your own pace; in Vatican City, a tedious guide can hold you back from getting to the Sistine Chapel at the end as it fills up by the minute. I give my €24 skip-the-line Colosseum ticket, which included VIP access to its downright peaceful attic section high above the throngs, an emperor-sized thumbs-up.

I’m not going to tell you to skip Italy’s greatest hits, but don’t let them distract you from its lesser-known delights. Rome’s Trevi Fountain is a classic, but Bernini’s Fontana dei Quattro Fiumi is a low-key masterpiece (plus, you don’t have to contend with pushy selfie-seekers, or pay to see it). The Ponte Vecchio’s bustling jewellery shops in Florence are cool, but the Ponte alla Carraia will take you straight down Via dei Serragli, which has the city’s best shopping.