Ah, Cortona – a charming hilltop town nestled in the heart of Tuscany, Italy. If you're a fan of quaint villages, stunning landscapes, and a touch of cinematic nostalgia, then Cortona is a must-visit destination on your Italian itinerary. My journey to Cortona began in Florence and after an hour and a half of winding through picturesque Tuscan countryside, I arrived at the Camucia-Cortona train station. The station is by no means a hive of activity however, little did I know that my adventure was just beginning.

Whilst all my research indicated there a bus from the station to Cortona operated on a Sunday, in true Italian style it seemed that in reality public transportation in Cortona operates on a slightly more relaxed schedule on weekends. With the bus service running infrequently, I found myself faced with a 2.5km uphill trek to reach the hilltop town. Armed with my trusty Ventolin puffer, I embraced the challenge, thinking, "Who needs a gym when you've got these views?" Plus, unless I wanted to wait another hour for a bus that probably wouldn’t arrive, I had no choice.

In the end, the uphill journey proved to be a blessing in disguise as it allowed me to fully appreciate the beauty of the Tuscan landscape. Rolling hills dotted with olive groves and vineyards stretched out before me, each bend in the road revealing a new postcard-worthy view. It was a reminder that sometimes the journey is just as rewarding as the destination itself. Finally reaching the summit, as I entered the town through one of the many medieval archways, I was greeted by the sight of Cortona's ancient streets winding their way through the town. Reminiscent of other Tuscan towns such as Pienza and Volterra, Cortona is charming with its cobblestone alleyways, ancient stone buildings and quaint piazzas.

One of the highlights of my visit to Cortona was exploring its many historic landmarks. The town's rich history is evident at every turn, from the imposing fortress of the Medici Fortress to the beautifully preserved Etruscan walls that encircle the old town. Walking through Cortona feels like stepping back in time, with each corner revealing another piece of its past. Of course, no visit to Cortona would be complete without a visit to the Piazza della Repubblica. This bustling square is the heart of the town, lined with charming cafes and shops where you can sample the local cuisine and pick up some souvenirs to remember your trip by.

When I arrived at Piazza della Repubblica, a large crowd was gathered for a mini-marathon for the children of the town.  An inflatable arch was erected and families of three generations were gathered to cheer on their young ones. The atmosphere was fun, frenetic and full of energy.  I grabbed a coffee and cornetto from a bar and took a table outside to breathe in the festivities, it was truly wonderful.  This Piazza is especially recognisable to fans of literature and film as Cortona holds a special allure thanks to its association with Frances Mayes' bestselling memoir, Under the Tuscan Sun. Piazza della Repubblica is where the famous fountain scene was filmed, and whilst the movie adaptation may have taken some liberties with the town's depiction (the fountain does not exist in reality), there's no denying the allure of Cortona's sun-drenched streets and rustic charm.

I wandered the streets for a couple of hours sampling local delights, adding some vintage posters and ceramics to my souvenir collection before hunger steered me back to the Piazza in search of a cold cocktail and delicious eats.  By this time a busker had taken up residence and was serenading locals and tourists alike creating the perfect atmosphere for a lover of people watching. Armed with a beverage and selection of salumi and cheeses, I truly relaxed into Sunday, pinching myself of how lucky I was to be there seeing the town that was featured in my favourite film.

As the sun began to dip below the horizon, casting a golden glow over the town, I couldn't help but feel thankful for seeing through my dream of living in Italy. Cortona is like all of Italy, it's a place where time seems to stand still, where the beauty of the past is preserved for future generations to enjoy. But as they say, all good things must come to an end and what goes up must come down, so as I made my way back down the hill to the train station, I couldn't help but feel grateful for the opportunity to experience the beauty and charm of Cortona.  

If you find yourself planning a trip to Tuscany, which if you travel to Italy I highly recommend you do, be sure to carve out some time to visit Cortona. Whether you're a history buff, a foodie, or simply in search of a slice of a tiny Tuscan town, Cortona has something to offer everyone. Just be sure to pack your walking shoes and maybe don’t go on a Sunday unless you need to dramatically add to your step count.