Happy Birthday….With Love, Tuscany

My birthday this year was exceptionally simple, exceptionally memorable and exactly what I needed and wanted. My birthday is November 30 and I love that my birthday is in November. This has nothing to do with anything, I realize this. I also realize that it is now March and that I’m about to write about birthday festivities that happened four months ago. (Bear with me here.)

Since I was at that time living in a secluded gem of a place, Fonterutoli, in the heart of Chianti Classico, my birthday wish was simple: Gallivant through Tuscany on a food, wine, and travel adventure that would make a wanderlusting-glutton jealous. With of course my trusty side-kick, my sister, by my side, I honestly could not have imagined anything better.

November might not seem like a great time to visit Tuscany. The harvest season has come and gone. The fields are barren. The days are short and often gray and heavy. The November sun is low and the fog is dense and abundant, especially in the early morning hours. But there is something quite beautiful in this too. To me, this region is glorious any time of year.  I know it seems cliché, an American who loves Tuscany, but for me there is something more at work here. There is something about the landscape, which makes me feel expansive and vast yet tiny and insignificant at the same time. It is my soul moving in time with the universe. When standing upon Tuscany’s hilltops the land ripples out from my feet, spreading out before me, creating dips and peaks, basins and mounds with villages and secrets tucked gently in its folds. The horizon is far and wide and I squint hard in hopes of understanding where it finally meets the earth or rather imagining where it leads, far behind the mountains.

As we set out on our afternoon drive, the warm November sun guided us as we drove from Castellina in Chianti down through Siena and eastward towards Cortona. Much has been written about Cortona, I know, and it even served as the backdrop to Francis Mayes book, Under the Tuscan Sun. Of course I had seen the movie, several times actually, but was still curious about this tiny town. As we zipped along, the weather was perfect. We were excited and discussed one of the most important aspects of the day, food. However, as we eagerly chatted, our destination drawing closer, the weather suddenly turned. The sun disappeared rather abruptly and instantaneously we were immersed in a dense fog.  The change was so immediate that I distinctly remember thinking it seemed as though a line had been drawn, a clear demarcation between blue skies and sun on one side and a grey mess on the other. My mood also completely shifted. I was thoroughly irritated. We wouldn’t be able to enjoy anything now. All I had wanted on my birthday was a nice afternoon, filled with small discoveries, quiet strolls and hidden places. When we set out I hadn’t thought about the possibility of the weather being so radically different an hour and a half away. I was annoyed that I hadn’t planned better, that we didn’t leave earlier. I had wanted it to be so perfect and now everything was ruined. I even entertained the idea of turning back but we had already come this far and I really wanted to experience a new place on my birthday. So we decided to continue on, slowly making our way through the flat, low plain before beginning our ascent to Cortona.

Cortona, situated on the border of Tuscany and Umbria, is perched quite high upon a hill with a wide and long valley just below it, and hills and mountains fanning out behind it. I actually was not aware of just how high up it was until we began zigzagging to the top.  Almost as quickly as it had blanketed us, so did the dense fog begin to thin out and lift. Forms began to immerge. Country houses and olive trees became distinguishable. Rays of sun pierced through the clouds, cracking their heaviness and breaking them open. Everything shifted once again, including my mood. As we continued, the sun shone stronger and the hazy sky turned brighter. In that moment, I realized that it was not actually the weather that was changing but our ascent, our moving through the unwanted to reach to the destination, which was causing the change. The valley had provided us with a vastly different experience. It was as opposite as night and day. Reaching the top, light completely surrounded us and Cortona welcomed us.

Now on foot, we made our way uphill past the old city walls, walking along the quiet cobblestone streets, enjoying the medieval architecture and admiring the quaintness. One of the most appealing aspects of Tuscany in the late fall and winter is scarcity of tourists. It’s as if you have it all to yourself. Albeit sunny, the November afternoon mixed with the labyrinth of tight streets created blustery wind tunnels. We needed something warm that would sustain us during the next few hours of aimless wandering and enjoyment. We ducked into one of the first bars off the main square, Piazza della Repubblica, for a caffe, emerging after a few minutes energized. We continued on towards Piazza Garibaldi, which looks over the entire Valdichiana, or Chiana Valley.  What came next was by far the highlight of my weekend, and something that I could have never planned nor could I have foreseen as we were driving through the fog earlier on. In place of the patchwork of fields that one might expect to find, stretched out far before us was a sea of impenetrable white, completely enveloping the valley below. Cortona seemed suspended above this dense, white fluffiness, but at the same time as if it had risen out of it.  Only the occasional distant mountain peak punctured the cloudy cloak. Perhaps a completely clear day would have made for a better view for some but this view, exactly the way it was, was something breathtaking. That very moment made my entire weekend. The way everything had come together, in a way I could not have planned or imagined, to form a most perfect moment. That was my gift on my birthday. Cortona did not disappoint.

Cortona, Tuscany
Mystical and unexpected – Cortona – Tuscany – Italy



Cortona, Tuscany, Italy
Sun salutations – Cortona – Tuscany – Italy

We let our gaze wander, marveling at the clarity of the day from the hilltop, basking in the bright fall sun, and breathing in crisp, clean air. The next few hours were spent exploring Cortona, taking pictures, ducking in churches and small shops, and curiously following those streets that called to us more than others. As the sun fell and temperatures dropped, we headed towards one of the many enoteche in the village for an aperitivo, two glasses of local red wine and Tuscan crostini, perfect together before dinner.

We found our dinner spot, Locanda al Pozzo Antico, by chance. Walking past, I peaked inside and immediately had a good feeling. I quickly scanned the menu. This was it. Being a Saturday night, we were lucky they had a table for two. The tables are few but the atmosphere is warm and inviting, rustic yet elegant, like Cortona. The crackling of the stone fireplace, the kindness of the family who owns and runs the restaurant,  and the simple, traditional and local Tuscan cuisine made this restaurant, which is more like a trattoria or osteria, feel familiar. With great enthusiasm and pleasure, we feasted that evening on pappardelle con cinghiale, ribollita, two secondi of roasted meat and a bottle of local red wine. The pasta is hand-made, the meat is sourced locally, and the food is authentic and prepared with care. Of course, it being my birthday, I could not do without dessert and a digestivo, a definite must after any large meal in Italy! For me it was a perfect culinary ending to a most perfect day.

Doesn't get much happier than this - Cortona, Tuscany (Italy)
Doesn’t get much happier than this! – Cortona, Tuscany (Italy)

This experience was worth more to me than any other “thing” I could have received. As I learn to make the small things the big things, I seem to be discovering more joy in my life. I am fortunate that I get to discover this, and other transformational realizations, in Italy, a country where there is no shortage of beauty that comes by way of simplicity.

How to reach Cortona:

By car, train, plane or bus

Where to eat in Cortona:

Locanda di Pozzo Antico

Via Ghini, 14 – Cortona (Ar)

Tel. 0575 62091 – 0575 601577



Reservations are recommended. I should also mention there is a B&B located next to the restaurant which is run by the same family.

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