To most seasoned travellers, the mere mention of Tuscany will evoke images of rolling hills and sun-kissed valleys, vineyards and centuries-old towns, cobbled piazzas and historic churches.

It’s a pretty accurate characterisation: the central Italian region – where Florence, Pisa and Siena are – does offer all that and more, making it one of the most popular destinations in the boot country after Venice and Rome.

For me, though, it’s one specific trip and one lesser-known town that’ve turned Tuscany into one of my all-time favourite places in my own home country – and the first one I’ll visit once the coronavirus pandemic is behind us.

In July 2017, my dad, my sister and I took a weeklong road trip to the region. It was our first holiday as a trio in a few years and, as it turned out, the last (we were planning something for this summer, but it doesn’t look like it’s going to happen). My sister, who’s ten years younger than me, felt a lot more mature than the last time I saw her: more adult, less sulky teenager. My dad was pretty thrilled to have us both with him. There were no arguments, no stresses – pretty miraculous, given it was a family vacation.

At a time when I am not at all sure when we’ll be in the same place, let alone the same room, again (I am in Hong Kong, he’s in Rome, she’s in Bruxelles: seeing each other in person is currently pretty much impossible), the memory of it has turned into a sort of happy place in my (our) minds – the type of armchair travel destination we all keep reminiscing in our weekly calls, not just for the sceneries, but for how uncomplicated life felt back then.

One spot, in particular, caught our collective hearts: Cortona.

A charming town in the Valdichiana (or Chiana Valley) in southern Tuscany, this sleepy urban centre was the base of our weeklong stay, and a delight of a destination in its own right.

Enclosed by stone walls dating back to Etruscan and Roman times and sitting pretty 600 metres up a hill, it gifted us with views that seemed to be straight out of a painting; a museum, the MAEC (The Etruscan Academy Museum of City of Cortona), filled with artefacts dating back to the 8th century BC; two major heritage sites — Santa Margherita Sanctuary and Girifalco Fortress, both on the top of the hill and a lesson in Italian history – and a streak of buildings and squares that have been standing since the 1200s. Just outside the city, “Le Celle,” a 13th century monastery built by San Francis of Assisi, offered a stunning place of silence and mysticism.

Further afield were big, lush nature, farms selling the freshest of produce, and cattle leisurely roaming the fields (Tuscany is famed for its Chianina , the oldest, high quality bovine breeds bred in Italy, whose meat is praised worldwide).  

But beyond the sights, it was Cortona’s lifestyle, which we embraced wholeheartedly, that made us fall hard for the place.

Our Airbnb, an old but airy apartment on the top floor of a rickety building, faced the Valdichiana hills on one side and the main square, Piazza della Repubblica, on the other, making us feel as if we were right in the thick of it all. A corner bakery would send whiffs of freshly baked bread and pizza bianca our way early in the morning; while every evening at 7pm local wine shops would offer degustazioni (tastings) of their tipples and cold cuts to residents and tourists alike. Unsurprisingly, we became regular customers of both.

Niconne Valley, Mercatale Cortona (AR), Italië

Small but perfectly formed restaurants lined the city’s narrow lanes, serving up classic Tuscan dishes: pappa al pomodoro (a tomato and bread-based soup), ribollita (a vegetable-rich minestrone also featuring lots of bread in it), pappardelle al sugo di cinghiale (egg noodles with a wild boar and red wine-based sauce). We tried them all (or as many as possible in seven days), the owners quickly learning our names, making suggestions on what to order and sharing their grappas and homemade liquors with us at the end of our meals.

We ate, we wined, we ate some more. But we also watched elderlies setting up to play their games of cards every afternoon, had lengthy conversations with the barista that made our coffee – something pretty much unheard of when you live in a big city – and with each other, and moseyed the main street Via Nazionale, referred to by locals as the Ruga Piana (Flat Street) as if we had nowhere else to be. Which was the whole point: we strived to slow down, catch up on each other’s lives, and sort of be in the moment, as cliché as it might sound.

Now that everything feels so uncertain, it’s that laidback attitude I find myself missing the most, but also the connections we made, with each other and the people around us. I can’t wait to go back.

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