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Home / Travel

Italy: Finding paradise in the imperfections of Cortona

By Kate Watson
NZ Herald·
23 Sep, 2019 11:00 PM9 mins to read

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Cortona, high in the hills of Tuscany, is the perfect spot for visiting some of Italy's great sites. Photo / Supplied

Cortona, high in the hills of Tuscany, is the perfect spot for visiting some of Italy's great sites. Photo / Supplied

Kate Watson finds paradise high in the hills above Tuscany

Abruptly turned away from the sixth restaurant in a row and our exuberance at being in this incredible medieval town is waning. What's going on? The explanation comes via a friendly waitress at Birrificio Cortonese, a little off the main drag and where, thankfully, there is space for our family of four.

Our arrival in Cortona, we are told, coincides with the Cortona Mix Festival, a five-day celebration of books, music, cinema, theatre, culture and wellbeing. As it also happens to be a Saturday night, so many restaurants are fully booked. Grateful to have found a friendly and affordable establishment that serves the requisite pizza and burger for our kids, we relax and take in our surroundings.

The town is unbelievably beautiful. Perched high in the Tuscan hills, it was originally an Umbrian city. It was conquered and enlarged by the Etruscans then colonised by the Romans and Ghibellines before eventually becoming part of the Kingdom of Italy in the 1800s. It is a maze of stone steps, medieval architecture, narrow winding streets and hidden alleyways embracing character-laden shops restaurants and boutiques.

It houses the Museo dell'Accademia Etrusca, which displays items from Etruscan, Roman, and Egyptian civilisations, as well as art and artefacts from the Medieval and Renaissance eras. In its Diocesan Museum are two surviving panels by early Renaissance painter Fra Angelico.

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It took a fair bit of most enjoyable research to settle on Cortona as a base for our week in Tuscany. There is a lot out there on Airbnb but a good number of villas are rural, meaning a car is needed to get to towns and restaurants. The villa we settled on has the peace and views of a rural Tuscan setting with the close proximity of local attractions.

Exploring the town of Cortona. Photo / Supplied
Exploring the town of Cortona. Photo / Supplied

It was built about 10 years ago in traditional Tuscan style and is split into a pair of two-bedroom residences, one upstairs, one down. Our upstairs apartment is beautifully finished and roomy with a large kitchen/lounge/dining area and two bedrooms with balconies opening out to the back garden and olive grove. It is completed by a generously proportioned pool which overlooks the lowlands below. A welcoming Kia Ora sign adorns the lounge wall, a gift from previous Kiwi guests, of whom our hosts speak fondly.

Reviews inform me that the town is a steep 20-minute walk up the hill from our chosen villa and having just made the three-hour drive from Rome, we are keen to see if this is the case.

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Our host directs us to a mown path from the back garden which leads us up through their family olive grove to the footpath-less main road. From there, we must cut through another property and climb several steep flights of steps. Eventually, we'll arrive at the main carpark, from which visitors can ride escalators to the town entrance. A few wrong turns mean it takes us a little longer than 20 minutes but it is a picturesque walk and as it is after 7pm we don't have to contend with excessive heat.

After dinner we follow the sound of music to the town square. Chairs are laid out in front of a large stage where two extraordinarily gifted pianists duel. Subsequent research informs me they are Andrea Bacchetti and Michele Di Toro — and they are giving a (free!) concert. We seat ourselves in the front row and watch the play-off. I can't take my eyes off Bacchetti, whose fingers itch to touch the keys every time Di Toro plays. On several occasions, they get perilously close to the keyboard. He wraps his arms around his body in order to prevent himself from doing the unthinkable.

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We return to our villa and sleep soundly, awakening to the faint sound of crowing roosters and distant bells from one of the town churches.

The heat is in the 30-somethings. We spend the day chilling by the pool, reading, swimming and relaxing. In the setting sun, we make the walk up our private path into town where we have booked dinner at what TripAdvisor tells us is Cortona's No. 3 restaurant, Osteria del Teatro.

Cortona is unbelievably beautiful. Photo / Supplied
Cortona is unbelievably beautiful. Photo / Supplied

The restaurant is full of atmosphere, the walls adorned with photos of famous actors, most of whom precede our time, though I do spot autographed pictures of Anthony Hopkins and Ralph Fiennes.

The restaurant gets a Michelin mention but we aren't blown away by the food itself. The wine list (or more accurately, menu) however, is incredible and although we order only by the glass, both our reds are sublime and well-priced.

A point of difference is the women's toilets. These are rather spectacular (some might say spooky), being filled with an impressive array of porcelain dolls, one of which is so creepy I actually awake with a start later that night upon seeing her snarling grin in my dreams.

The next day, we take a trip to Valdichiana Outlet Village. It houses an extensive compound of predominantly fashion and sportswear shops from Adidas to Tommy Hilfiger with some Italian brands thrown in. The discounts aren't that obvious and the overall experience differs little from shopping at home but it is an enjoyable way to while away a few hours.
A 20-minute drive takes us to Lake Trasimeno, where the kids talk us into hiring a family-sized paddle boat contraption, with dual pedals and a slide. Despite being deliciously warm, I can't be persuaded to swim in the murky, weedy water but the kids have a ball. The sand in the shallows is silty black ooze; the kind you can imagine someone paying to be massaged with because of its purported healing properties.

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Due to the conflicting information provided on the various websites and forums, we spend a good couple of hours planning our trip to the Leaning Tower of Pisa and Florence's Duomo the following day. Reviews tell us we must purchase "skip the line" tickets, but don't tell us where to buy them and as the tower climbs have designated schedules anyway, we are baffled as to the merit in this. Realistically, how many people are we talking here?

To climb the Leaning Tower of Pisa is worth the cost. Photo / Getty Images
To climb the Leaning Tower of Pisa is worth the cost. Photo / Getty Images

Nervously, we fork out for tickets from the websites themselves. At €112 (NZ$186) for the four of us to climb Pisa and see the cathedral, and €108 (NZ$180) for the Duomo, they aren't cheap but our 10-year-old son is particularly invested in seeing Pisa, so being able to actually climb it is an unexpected bonus.

Pisa is a two-and-half-hour drive from Cortona. We park up, emerge into the hairdryer-hot sunshine and there, at the end of the street, is the tower. I am unprepared for its beauty and that of the Square of Miracles where it sits. The tower, and its neighbouring cathedral are stunning. While there are the expected throngs taking selfies and being photographed "pushing up" the tower, the green expanse of lawn directly in front of the buildings helps create an overall feeling of beauty and spaciousness.

The 294-step climb up the tower is well worth the euros. The lean is physically discernible upon entry and the climb itself not as arduous as we feared, with solid steps and plenty of ventilation to provide respite from the 41C outside. We emerge to the outer balcony, from which we're able to look down on the cathedral and town below.

The 11th-century cathedral is beyond spectacular inside and out, with so much to take in, one hardly knows which way to turn. The artworks adorning the walls are off the scale, the golden ceiling (added in the 16th century after the original wooden ceiling was destroyed by fire) is a visual masterpiece.

It is a 90-minute drive from Pisa to Florence and the kids and I are grateful for the opportunity for a nap. On arrival in Florence, we spend a few hours window shopping before our Duomo climb at 6:30pm. This particular pocket of Florence is leather, leather and more leather. The shops start closing around 6pm, which seems incongruous given that it's only after 6pm that the temperature becomes less hairdryer and more heater, making it more pleasant to walk the streets.

At 114m, the cathedral dome is 57m higher than the tower of Pisa — an additional 169 steps. I still have vivid memories of climbing it as a 7-year old, my younger brother cowering against the walls at the top, too scared to look down. Kids that young are discouraged now — for good reason: once you start the climb, it is difficult to turn back. If you are in good health and are prepared for a couple of claustrophobic spots where it gets pretty tightly packed, it is worth the effort.

Sure, it doesn't pay to analyse the potential health and safety risks too closely but frankly the absence of staff or emergency exits along the way are what make the whole experience feel so organic. Like the Tower of Pisa, the Duomo stairwell is well-ventilated and there are spots on the way up where you can pull over and have a rest. When you finally emerge out on the balcony it is mind-blowing. Unlike Pisa, there is no high mesh wire obstructing your view; at chest-height, the rail affords a proper look at the city below.

By the end of our week in Cortona my husband has a favourite morning cafe at the town entrance. It serves a mean espresso and an incredible crispy-fresh cornetto alla crema, like a custard-filled croissant.

Accepted attire being on the dressy side, I leave in sneakers for our dinner climb up the hill then change into fancier footwear on the convenient stone stool at the base of the escalators. We have head torches for the walk back.

On our final evening, I see something sparkling in the grass path. It is a spider, brown, large-ish by New Zealand standards. Suddenly our torches are picking up dozens of tell-tale glows; turns out we have been unwittingly walking among these Tuscan arachnids all week.

This brings me to my own philosophical musing on travel itself. Whether consciously or unconsciously, I believe many of us travel in search of a perfect paradise. But surely, it is its very imperfections that make paradise what it is.

Paradise is the cracks in Vasari's Duomo di Firenze ceiling fresco. It is the lean in the Leaning Tower of Pisa. It is the spiders lurking in the grass behind a villa in Cortona.

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