Exploring Italy’s City Streets and Country Roads

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The view of the Umbrian countryside from the top of Orvieto. Photos by Mike Crisalogo

Travelling from Rome to Venice via Umbria and Tuscany’s country roads

The last trip my grandmother and father ever took in Italy was more than 60 years ago, from the family home in Sicily toward the port where they’d board the MS Vulcania and sail toward a new life in Canada.

By contrast, my last ride in Italy was aboard a luxury coach with extra leg room, courtesy of my host Insight Vacations, during a press trip to sample their Country Roads of Umbria and Tuscany tour. With tour guide Belinda – a virtual encyclopedia of all things Italy – at the helm, our ride from the Eternal City to the Floating City included stops in ancient towns and saintly landmarks, meals with celebrated Italian chefs and dessert with a world champion gelato maker, as well as a visit and lunch with a bona fide Italian count.

Click through for a full account of my seven-day journey along some of Italy’s most picturesque country roads.

View from the top of the Bramante Staircase in the Vatican Museums.


DAY 1: We land in Rome on a drizzly Friday evening. I meet many of my travel companions on the Insight coach at the airport. A number of them are journalists from Australia. Sadly, I have little frame of reference about Australia outside of what I learned from the Crocodile Dundee films. I mention I’m from Toronto. Sadly, they have little frame of reference about Toronto outside of what they heard following Rob Ford’s exploits. So, naturally, we get along swimmingly.

Rome’s Piazza del Campidoglio on a rainy evening.

Our group stays at the palatial five-star Regina Baglioni Hotel. And palatial is barely an exaggeration. There isn’t much time to jump up and down on the massive bed in my room, though, as we head out for an evening tour of the Eternal City that culminates at Michelangelo’s staircase, the rain-soaked and the ruins of the Capitoline Hill.

After the tour we dine at the 4 Colonne Roma (Four Columns restaurant), while serenaded by a raven-haired soprano in a black lace dress.

DAY 2: Thanks to our host’s connections, we skip the long lines and tour the Vatican Museum and the Sistine Chapel before climbing the winding Bramante Staircase – which is usually closed to visitors – built in 1512 to allow Pope Julius II to ride his carriage all the way into the Vatican. Not a bad way to spend the morning.

The view of the Umbrian countryside from the top of Orvieto.


Outside of Rome our coach pulls over next to a massive rock formation in the middle of the Umbrian countryside. This, our local guide Marco tells us, is Orvieto: an Etruscan built, Roman-claimed village built high on rock that he likens to “a piece of Swiss cheese”. And how do you get up to the village? Why, an elevator of course.

Chef Lorenzo Polegri pours a sampling of his six-hour old olive oil.

It’s not clear if the Etruscans or the Romans installed the shiny steel elevator but, once at the top, Chef Lorenzo Polegri and his wife Kimberly take us on a brief tour of the town (including the breathtaking view of the countryside) before a toast with Prosecco and cheese in their yet-to-open restaurant. Later, in their current restaurant, the award-winning Zeppelin, Lorenzo offers a lesson in homemade pasta-making before a lunch that includes thick, green, six-hour old olive oil from Lorenzo’s own olive grove.

From Orvieto we drive to Marco’s birthplace of Perugia, land of Baci chocolates and ceramics. An evening stroll through its famed underground city reveals a mass of residents celebrating a street festival. Dinner at Ristorante Pizzeria Ferrari begins with an appetizer of pizza before a main course of more pizza (no complaints – they were both delicious) before a late-night ride on a Merry-Go-Round near the city centre.

Assisi’s picturesque sloping architecture overlooks “terra dei santi” – the land of the saints.


DAY 3: We wake to the sound of church bells ringing across Perugia before heading to one of my favourite destinations: Assisi. On the way Belinda gives us the lowdown on the town: it’s the fifth most visited city in Italy thanks to the pilgrims who flock there; it’s also the arch-rival of Perugia (sorry Marco); one of its churches, St. Mary of the Angels, is the 7th largest in the world and more saints hail from the region of Umbria than anywhere else, giving the region its nickname la terra dei santi or “the land of the saints.”

As we exit the bus Marco points to the town, raised high on the hillside. “The best way to go back to the Middle Ages,” he exclaims, “take the escalator!”

Then he points to an escalator that scales the hillside and drops visitors right near the town’s gate.

Once inside the town, the exquisite views of the Umbrian landscape, the picturesque piazzas and the historic churches and relics that pay tribute to the city’s two most famous saints – St. Francis and St. Clare – almost overwhelm. Church bells across the town chime on the hour and a part of me wishes we don’t have to leave.

We do leave, however, stopping at Emmanuel Ragani’s 60-year-old olive grove, where his grandfather started the family olive oil business in 1956. In Italy, olives and olive oil are known as green gold and we sample a drizzling of a fresh batch on bread toasted in a stone over before we head for Spello.

Spello’s streets are empty on a Sunday – a stark contrast to Assisi’s bustling piazzas only a 15 minute coach ride away.

On this Sunday, Spello, another hilltop town, is virtually empty – an incredible contrast to the bustling Assisi that’s only 15 minutes away by coach. They also don’t have an elevator or an escalator, so we actually have to climb stairs to get into town. Get with the program Spello!

Despite making us use our legs, touring the empty streets was a surreal experience, capped off by a huge dinner courtesy of Chef Francesca at a local restaurant. In the evening, as we pull away in our coach, the lights of the town sparkle like a constellation on the hillside.

The morning mists make their way through the valley surrounding Cortona.


DAY 4: We spend the morning gliding through the mists of Umbria, past hills dotted with watchtowers, farmhouses and olive groves. We also spot Lake Trasimeno, where Hannibal and his army of 40,000 ambushed and slaughtered the Roman legion.

Eventually we cross into Tuscany and stop in Cortona, protected by its patron saint, Saint Margaret of Cortona, its 2800-year-old Etruscan stonewalls and a row of 600 Cyprus trees – one for each boy from the town killed in the First World War. Our coach carries us up the winding road to the town’s gate, where my notes from the trip confirm that I, “literally don’t know which way to look – the misty valley below or the historic town above.”

We’re told the fields in the valley below were planted strategically, like a painter composing a landscape, to be pleasing to the eye when viewed from above. The town, meanwhile, bustled with residents in their 70s and 80s navigating the steep streets. Cortona is also known as the home of author Frances Mayes, author of the memoir-turned-movie Under the Tuscan Sun.

A sampling of the 3,000 barrels of wine in the winery cellar owned by Count Francesco Mazzei of Fonterutoli’s family for centuries.

Later, in Fonterutoli, we dine with Count Francesco Mazzei at his family’s winery – the full story of which I recall in detail here. Two important notes about the count is that, yes, he was a real count who joked his family “owned this property before [the time of] Columbus” and, no, he didn’t turn into a bat and fly around the room with a wave of his cape.

The cottages tucked away at Borgo San Luigi offer guests an authentic Tuscan country living experience.


From lunch with the count we make our way to The Borgo San Luigi in Monteriggioni, a 400-year-old Tuscan estate set at the end of a long, tree-lined driveway and encompassing a main house with guest rooms, a number of individual guest cottages spread around the property and a dining hall and outdoor pool in the building that would have once housed the stable.

Basically this is a Tuscan dream – the perfect hideaway complete with a swath of early morning mist draped across the field outside my cottage door when I wake up for breakfast the next day.

San Gimignano, dubbed the “medieval Manhattan” for its towers, looms over the Tuscan countryside.


DAY 5: A day trip brings our coach to a standstill on the side of a dirt road and one of the most striking views in Italy. Across the vast grape fields stands the town of San Gimignano, its towers looming high over the countryside like diligent men-at-arms.

The town, virtually abandoned during the Black Death in 1348, is “one of the most perfectly preserved Middle Ages towns,” Belinda notes. The region is also popular with the celeb set looking for a country getaway, including rocker Sting, and filmmakers, who’ve filmed flicks like The English Patient and even Twilight here.

Two-time world champion gelato maker Sergio Dondoli serves up scoops at his shop in San Gimignano’s Piazza della Cisterna.

Dubbed the “Medieval Manhattan” for its many towers, a tour of this gem brings us everywhere from a walk along the town’s walls to the shop of two-time world champion gelato maker Sergio Dondoli, whose enthusiasm for his work is almost as exciting as the gelato he piles into cones and cups for us. The inventor of saffron cream gelato, he boasts, “At home, if you are unlucky, the ice cream you buy is six months old. In my shop, if you are unlucky, the gelato you buy is 24 hours old.”

Sipping vino in Bichi Borghesi Estate’s converted stables before dinner. The round cages on the wall used to hold hay for the horses.

Bichi Borghesi Estate

With memories of San Gimignano and Dondoli’s gelato still dancing in my head, we arrive at the Bichi Borghesi Estate for a wine tasting and dinner. It’s a fun night, but the memory that stays with me is the magnificent, refurbished old stable that we sipped our vino in before dinner.

One of the many classic rides that greet visitors at the Museo Ferrari.

Maranello – Museo Ferrari

DAY 6: We leave the Tuscan estate and head for Venice, with a few stops along the way, including the town of Bologna, where we wander and grab lunch, and Maranello, which racing fans will recognize as the home of one of the most celebrated car manufacturers in the world: Ferrari.

I’m not a car or racing buff, but the energy is still palpable when visiting the heart of a town that is built around the production of this renowned automobile. Like works of art on four wheels, the evolution of these cars is charted in chrome and red paint at the Museo Ferrari, with many models on the floor for visitors to get up close with.

From Museo Ferrari, it’s off to a city where cars don’t exist – a city that also happens to be number one on my bucket list of destinations to visit: The Floating City, Venezia.

Gondolas at dusk, before a flood of tourists awake.


Before we reach the port to catch our boat ride into Venice, we spot a fisherman standing in his boat, a lamp on the bow cutting through the dark of the night straight into the water where he waits patiently for a catch of squid or cuttlefish.

Once aboard our water taxis we navigate the Grand Canal into the heart of Venice, the clamouring of church bells marking our arrival. This is likely the only time I’ll ever stay in a five-star hotel in the heart of Venice – the Hotel Bauer – with view from my hotel room that takes in both the city’s historic rooftops and the gondolas gliding past in the canal below.

A short, pre-dinner walking tour intersects with the candlelit procession of the Festival of Madonna Della Salute through St. Mark’s Square – a gesture of thanks for deliverance from the plague. Eventually, Belinda leads us through the back streets and hidden coves of Venice to the Ristorante Antigo Pignolo – tucked away in a remote pocket that dates back to the year 1200, where it was a blacksmith’s shop and eventually a bakery run by local nuns whose convent occupied part of the property. On this evening we get a private room and, though we leave with full bellies and heavy eyelids, it’s a chore to force myself to bed in a city that exhales vitality with every wave that crashes against the shoreline.

A boy wades through aqua alta in St. Mark’s Square. This occurs when the tides rise to the point they breach Venice’s shoreline.

Venice Part Two

DAY 7: I wake up early on our only full day in Venice – so early in fact that the sun is barely above the horizon and the pigeons are still snoozing on various Venetian stoops. Camera in hand I snap some shots of the sleepy city and gondolas that, in a few hours, will be packed with tourists. I stop into one of the only open cafés for an espresso while a gentleman sweeps St. Mark’s Square and boats begin to dock, bringing workers into the town in what is clearly Venice’s version of “rush hour.”

St. Mark’s Square reflected in the acqua alta.

Once the city is awake our group tours the city by land and water, followed by a glass-blowing tutorial and then shopping and free time. In the meantime, acqua alta – when the tide rises and floods the city streets – engulfs large sections of the city, resulting in the quick assembly of an intricate cross-section of platforms that allow pedestrians without rubber waders or plastic shoe covers to get around. For the most part people have fun with it – adults take photos and kids frolic and splash in the streets.

Later, we dress up for a drink at one of Ernest Hemingway’s old haunts, Harry’s Bar, where we sip their famed Bellini before navigating the city’s spectacular waterways aboard gondolas, serenaded by an accordion player and a tenor who even compels residents to stick their heads out of their windows to offer applause.

The evening ends with a goodbye dinner and drinks. Six days earlier we were a group of strangers and now we’re hugging each other goodbye with sincere hopes that our paths will cross again in another corner of the globe – perhaps, even, on some other country road.

Insight Vacations offers unique exclusives such as private Vatican tours and authentic dining experiences. For more information, visit www.insightvacations.com/ca or call 1-866-747-8120.

Have a memory of Italy’s country roads you’d like to share? Leave a comment below or tweet the author at @MikeCrisolago. And stay tuned for Mike’s story about rediscovering his family roots in Italy, coming soon…