A Traveler’s Guide To Italy’s Surprising Side

My first glimpse of Italy was a shroud of darkness spread out beneath the wings of an airbus.

We were supposed to fly into Venice as the sun set, which probably would have left a more striking impression: refracted light dancing off the Alps like a million campfires, dusky shards of land set in a sapphire lagoon.

Instead, our connecting flight out of Frankfurt was spontaneously declared “unfit for takeoff” while we were rumbling toward the runway. By way of apology, the airline gave us all a minuscule helping of chocolate and a two-hour layover in the Atlanta of Europe. By the time we reached Venice — not the old city, mind you, but the mainland — it was too dark and we were too tired to draw any conclusions.

My first real impression of Italy, then, was when I opened the blinds the following morning. The room was stuffy, my dreams had been fitful, and I needed to orient myself. Where was I?

Peering out over a rather pedestrian suburb, I noticed a veil of low clouds in the distance. They were steely lavender, with roofs like daggers.

“Great,” I thought to myself. “Day one in Italy, and it’s going to rain.”

But then I realized they weren’t clouds at all. They were Alps.

Suddenly, the delayed flight didn’t matter. My piecemeal sleep didn’t matter. I was in Italy for 12 days, and I was hungry for adventure.

Here are just a few of the things I discovered along the way. Maybe they’ll help you plan your Italian excursion.

Venice

That day, we took the ferry from real Venice across the lagoon to imaginary Venice — the Venice you see in the movies, the Venice that was once the seat of an affluent maritime empire but now serves as its tomb, the Venice that is sinking.

And stinking, quite honestly. My advice? If you’re venturing into the city, try to go on a sunny, breezy day. When it’s overcast, a faint odor of spoiled tomatoes clings to the air. It’s nobody’s fault: all those villas and piazzas rest on a millennium of mud, sludge, and excrement.

But don’t let that discourage you from visiting! No matter how many pictures or videos attest to Venice’s beauty, the real thing is more dazzling. I remember thinking: “People live here. In houses that have been inhabited for 600, 700, 800 years. To me, this bridge over a narrow capillary canal is a set piece out of high Renaissance drama; to some lucky Venetian, it’s part of the morning commute.”

Visit St. Mark’s square, and the Doge’s Palace, and take a ride in a gondola. (The gondoliers are tremendous sports.) But save some time to wander and get lost in Venice too. There are glassblowing workshops where you can watch artisans craft vases the same way they’ve done for generations, and boutiques where you can buy traditional Venetian masks.

And spare a Euro or two for the street performers who line the shore near where the ships and ferries dock.

Florence

After Venice, we began working our way down the boot of Italy.

Our next major stop was Florence, the epicentre of the Renaissance and home to some of Italy’s most cherished literary figures. It was here that Dante Alighieri wrote his Divine Comedy, and the shrewd, serpentine Machiavelli founded the modern state in his infamous treatise The Prince.

One thing you notice as you criss-cross Italy is that there’s really no one Italian language. Every region has its own distinct dialect; a sentence that makes sense to a Milanese may be borderline incomprehensible to an Umbrian. This is a legacy of Italy’s medieval past, when the peninsula was divided into a gaggle of squabbling independent city-states. (The country was only unified in 1861.)

But our guide, Matteo, informed me that Florence was the easiest place for him to visit because the Florentines speak the closest thing there is to standard Italian — a legacy of Dante, whose writings are considered foundational. One of Dante’s houses still stands in Florence, given over to a museum of his life and works.

You’ll also want to check out the iconic Cathedral, the Uffizi Gallery (where many treasures of the Renaissance reside), and the Palazzo Vecchio (a 13th century palace with a high tower you can climb for a few Euros).

But if you’re looking to practice your Italian, Florence is probably the best place to do it.

San Gimignano

Just southwest of Florence, in Tuscany, you’ll happen upon a fortified hill town called San Gimignano. No, it’s not one of the most famous (or pronounceable) Italian destinations, but it’s unspeakably beautiful.

San Gimignano is surrounded by walls dating to the 13th century, and guarded by numerous high towers. For my Euros, though they may not be many, this is the real Italy you need to see: the small hillside hamlet commanding a view of the rippling countryside, seemingly unchanged for centuries. It really is like stepping into another epoch.

If you’re not squeamish, there’s another little surprise waiting for you in San Gimignano: a torture museum. Though morbid, it provides an accurate look at the darker side of the history that’s so well-preserved in rural Tuscany. And you can always grab some gelato afterward to lift your spirits a bit.

Assisi

To the south and east, and a bit better-known, Assisi is another hillside town you mustn’t miss. Instead of fortifications or torture chambers, the draw here is the life of a Saint.

St. Francis of Assisi (1181-1226) was born into a wealthy family of silk merchants and minor French nobles. His early life was supposedly devoted to lavish spending, fine clothes, and entertainments. However, St. Francis quickly became disillusioned with his life of privilege, and took to giving everything away to the poor.

According to hagiography, Francis’ charity was not well-received by his father, who imprisoned him, beat him, and ultimately forced him to renounce his inheritance as a means of repaying the fortune he had given away in alms. Francis subsequently became a monk and founded the Franciscan movement, which required adherents to forsake all property and material gain in emulation of Christ.

Francis’ tomb can still be found in his Basilica in Assisi, a spectacular Gothic church complex that juts out the side of a hill like the bow of a great ship.

I’m not a religious person, but when I was there, in St. Francis’ crypt, I was struck by the most peculiar feeling. I don’t know how to describe it. Perhaps it was partly a sense of awe and admiration for the man, and partly a sense that I had somehow stepped into history — or myth.

Whatever it was, everyone should experience it.

Naples and Pompeii

Driving south down the spine of Italy is an experience in itself, staring out windows at mountains and foothills, trying to get used to the somewhat hollow taste of Fanta.

As we got closer to Naples, our guide, Matteo, pointed out numerous half-finished bridges and infrastructure projects. A symptom of mafia-backed construction companies, he explained, who like to build half of something then charge the government extra to finish it.

Just outside Naples, Matteo took us to an authentic hole-in-the-wall pizza joint where the staff kept bringing us pie after pie with ever more exotic toppings. When they brought us escargot pizza, I thought they were spoiling us; when they brought us dandelion pizza, I knew they were ready for us to leave.

A few million people live around the Bay of Naples, with the terrible volcano Vesuvius lurking in the distance. But the real killer volcano lies beneath the bay itself, which is in fact a caldera.

Naples is the site of a supervolcano, a bubbling cauldron of magma collecting beneath the surface like a subcutaneous blister. When the pressure becomes too great (don’t worry — it takes millions of years) the blister erupts, blowing a massive hole in the Earth’s crust and ejecting enough poison into the atmosphere to constitute an extinction-level event.

Still, the real star of the show is Vesuvius, whose eruption in 79 AD buried the ancient Roman towns of Pompeii and Herculaneum, preserving them beneath deep layers of ash and rock, petrifying hapless citizens as they tried to flee.

Pompeii is one of the most famous destinations in the world, but there were still a few surprises.

I was prepared to see the plaster outlines of human beings scattered in the streets, frozen where they had died nearly 2,000 years ago. You will see no such thing, although you should be able to find one or two if you’re the kind of person who enjoyed the torture museum in San Gimignano. What you will find are well-preserved villa walls, an amphitheatre, and even original Roman pottery.

You will also find — how shall I say this? — ample representations of male genitalia. The Romans considered the male reproductive organ to be a symbol of strength and good fortune, and many Pompeiian villas feature graphic carvings on their outer walls, where in modern times you might expect to find a street number.

The penis is such a symbol of Pompeii that you may even see souvenir carts selling replicas. They make an excellent gift for a friend with a bawdy sense of humor.

As ancient and well-trod as the cobbled streets and hilly lanes of Italy may be, there’s still plenty there to surprise you. And plenty to change your point of view.