Travel /

Under the Tuscan Sun in Cortona

“I moved to Italy for love but work is what brought me here.”

Departing early from Milano Centrale for Cortona, I declined to use the nose plugs distributed by Frecciarossa staff under my mask. The train air offered breaths of disinfected hope. I had been to Cortona before but this was my post-vaccine maiden voyage. A reminder that covid travel restrictions had only just been lifted, it was mostly empty. A cluster of teenage girls in brightly colored masks celebrated the end of the school year, dozing in and out of TikTok sessions under their chunky headphones. I agreed to trade seats with one and we smiled with our eyes.

On the empty platform at Camucia, the dry Tuscan heat mixed with aglione, Val di Chiana’s spicy, giant and delicate cousin of garlic. A key ingredient in locally made tomato sauce which is then slathered over pici. Tuscany’s thick, hand-made pasta was just one of many reasons for my visit.

I once dreamt the word cliche was written on my forehead while waiting under a cypress tree for my Italian husband to pick me up on a seagreen Vespa. I moved to Italy for love but work is what brought me here. The amount of books and movies that have swept an international audience with Italophilia is vast and Tuscany has often played a starring role. Not one can compete, however, with the Cortona-set 2003 success of romantic comedy Under the Tuscan Sun. This novel and subsequent film played on our global wanderlust’s heart strings. Fittingly, I was meeting my Canadian friend who also had stayed in Italy for love; her partner who grew up in and around Cortona and the province of Arezzo has a vintage Vespa.

Jennifer’s dog Vizz jumped to sit on my lap when I sat down in her car. A short ride to the top, the ancient walled city looked down on us. Surrounded by an expansive agricultural valley, stunning churches and their opulent gardens, she shared the story of meeting her partner Saverio at a long shuttered discotheque called Vintage near the train station. An artist who’d kept a low profile in town she hid her romance with Saverio for months as he was a staple in Cortona’s salotto” and knew everyone. Saverio and their son Ivo met us at the top of Via Nazionale, Cortona’s Decumano, an east-west street. Many ciaos later to what seemed like almost half of Cortona’s population of 2000 people, we arrived at Casa Ermenegilda. This extraordinary palazzo emanates with historical beauty, restored as a holiday home for visitors who value space, design and simplicity.

Named for Saverios great grandmother Gilda (also the name of their adopted street cat), the seven stories once included bedrooms for all of Gilda’s grandchildren and a photography darkroom next to the cantina for her husband Carlo who was a passionate hobbyist. I relaxed in my room on the handmade LinnSui futon bed (designed by Saverio and his brother and featured in Sorrentino’s La Granda Belezza) and switched on the 1970s Guzzini Lucciola table lamp as night fell. Before closing the shutters to dim the noise from the recently reopened enoteca, I greeted a woman named Jeanette with Diane Lane vibes, a Californian who owned the B&B across the street. She “met” Jennifer in their tall windows for a daily tea during Cortona’s lockdown.  After a bowl of pici and grilled steak on Gilda’s marble and cast iron clad kitchen, Franco Battiato and Sangiovese soaked voices lulled me to sleep. 

Highly intertwined is Cortona’s community, much like the winding alleys and climbing stairways where the Etruscans once trekked. Maze-like streets and cars limited by parking and ZTL limited traffic areas, the temptation of surprising views into the valley beckons you to walk longer than you’d planned.

Jennifer jogs by Bramasole every morning and I joined her. Bramasole is the villa of Frances Mayes, author of Under the Tuscan Sun, where she lives for a few months every year. Mayes cleverly named it for the protagonist villa in Under the Tuscan Sun although it is not where they actually filmed the movie. It is said that thousands of tourists walk by it every year for a photo. I like to imagine they dress in a white shirt and khaki pants just like Diane Lane in the movie. We jog along the ancient walls, by an impressive wall overflowing with wildflowers and butterflies breakfasting, and rockstar Jovanotti’s estate; past the striking Gino Severini mosaic on Chiesa di San Marco; ending in a park that houses Cortona’s only fountain. Tourists still come to Cortona looking for the fountain where Diane Lane’s character jumps in like in Fellini’s La Dolce Vita.  A foam & fiberglass composite fountain was constructed in Piazza Signorelli for the scene; in the memory of locals Neptune’s body parts were highly disproportionate, says Jennifer.

Saverio and Jennifer take me to Castellani 1919 down the street from Casa Ermenegilda. Elina, who runs the business, maintains rows of cabinets full of objects and posters – vintage and rare – in her family for over 100 years. During lockdown, the three partnered up to create an ecommerce site with selected vintage objects from Castellani 1919, custom and handmade ceramics by Cortenese artist Guilio Lucarini, and playful vintage inspired signs whose designs Saverio unearthed from an abandoned farmhouse in a field outside Anghiari. In his 20s, Saverio was the friend who would call you for a ride at midnight on a Saturday, but not for a ride to the discotheque. Cruising the streets of Florence on his Vespa, his life as collector began when he learned that the abandoned bar chairs he’d salvaged (thanks to his friend that arrived with his 1980s Volkswagan van) by the side road were tossed by one of the most popular cafes in Firenze called Guibbe Rosse. The chairs were renewed and sold. This was just the beginning. He owns Emporium 1919, a props and vintage set rental company in Arezzo which services Italy with unique objects for film and commercial sets. Jennifer is an artist who worked in retail fashion to pay the rent, opening stores for Prada in Spain, Portugal and China.

On my final day in Cortona, we piled into their car–with Vizz in my lap, Saverio at the wheel and Jennifer and little Ivo in the back seat–on a quest for aglione. The ginormous bulbs sprouted in elegant rows as the sun began to set in the valley. A chef friend whose American family harvests olives every season at their farmhouse in the hills nearby told stories of this bulbous marvel. We filled the trunk and plotted our aglione dinner menu including a salty raw garlic and potato dip we spread over traditional saltless Tuscan bread. The next morning, my travel sack provided the ideal scent.


Jennifer & Saverio’s Guide to Cortona


Villa Tommasi (Pergo) 

Villa Boninsegni (San Angelo) On Booking

Relais Villa Di Piazzano (Villa near Orto Fortunato) 

La Terra del Cavaliere 



Osteria del teatro

Dardano (typical trattoria)

La Loggetta

La Grotta




Sotto voce