Summer Story Series: Katie Self's European Vacation Part 1 - Cortona, Italy

Up next in our Summer Story Series, Katie Self, Senior Marketing Coordinator, details her two-week vacation through Tuscany and Rome, Italy and the islands of Croatia via a catamaran. Given this was a two week vacation, this will be a three part series: Cortona, Rome, and Croatia.

Today she shares Part 1: Cortona, Italy.

I waited for this trip since September 2019, when I had to cancel a European adventure due to a family emergency. That trip included Copenhagen, Denmark; Oktoberfest in Munich, Germany; and a quick stop in Venice, Italy. Next, I set my sights on celebrating a milestone birthday with friends starting with the Chicago Cubs and St. Louis Cardinals game in London, England before moving on to the Amalfi Coast in 2020, and you can guess how that went. So after three years and two canceled trips, I was determined to not only make this happen, but I would do it in style with my favorite people and create a trip of a lifetime.

Our group eventually decided to move the trip from the Amalfi Coast to the islands of Croatia where we would rent a beautiful catamaran, manned with a skipper and hostess, and sail between islands across crystal clear blue-green waters. Still wanting to visit Italy, I decided to add a week beforehand and recruited one of my oldest friends to join me. We decided to fly into Rome and take the train up to the small town of Cortona, Italy, part of the province of Arezzo, for a few days. Movie buffs may recall Cortona as the town that served as the setting for the 2003 smash hit Under the Tuscan Sun.

The sleepy, Disney-like Tuscan town was, as expected, breathtakingly beautiful. The Etruscans, a civilization and culture that began circa 900 BC, built the town’s walls in the 4^th century BC. They remained until they assimilated with the newly established Roman Empire. Yes, Cortona’s roots go beyond the Roman Empire, and that means plenty of centuries-old architecture.

A private driver took us through the Cortona countryside for two wine tastings. Having visited Napa and Sonoma County, California, we envisioned hopping from winery to winery, tasting a few varieties at each. In other words, excessive, fast-American style. When we spoke to Alberto with Cortona Wine Tours, we let him know the extent of our wine knowledge (basically, “I detect hints of red,” or “I like rosé”, so…very limited) and he set up a day with the promise two locations would be more than enough. We visited two very small operations: Leuta and Agriturismo Via della Stella.

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A magic trick for getting more dessert wine when you think all is gone. Barrels storing wine at Leuta

The hit wine at Leuta was by far the 2018 Syrah, a variety that I typically shy away from. But again, with my limited knowledge, all I could tell you is it was probably the best Syrah I’ve had. Good enough to join the wine club and have a couple cases shipped to the States! The woman who hosted us is from New York, and we stayed for quite some time learning about her journey to moving to Cortona, she taught us about the process and walked us through the site. The sun was hot, but the breeze was cool and it was just the most perfect start to my first time in Italy.

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The process working its magic. Myself, Christina Brown, and Jennifer Criswell - ex-Pat and Leuta's Wine Club Manager

From there, we were taken to Via della Stella, a property that also serves as a hotel on sprawling acres of green. Wild tomatoes grow on the side of the road, and you’re welcome to pick and eat them straight from the vine. Bellissimo.

We were served an incredible 3-course lunch of homemade sweet raviolis, a cabbage, kale and white bean stew, plus beautifully cooked beef and potatoes with a side of cucumber and tomato salad. For dessert, a dense chocolate cake-like dream drizzled with caramel and espresso to keep us going. We were fortunate enough to thank the chef personally, even though I communicated through hand gestures. A universal language!

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Photos only do a disservice to how much flavor was in each dish

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Anywhere I go, I will find the animals, and there were plenty of pups at Via della Stella

Alberto was right: we only needed two wineries. The simple, relaxed and slow tour was what we needed to truly take in everything around us, chat with locals and appreciate everything in front of us. From here, Alberto drove us to the top of Cortona where we visited the Convent le Celle, the first monastery built by St. Francis of Assisi in 1211 – he lived here as well (growing up Catholic and forever an animal lover, this was a very fun fact.) Monks live here in the present day.

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Views of the Convent le Celle

We wrapped up the evening with more pasta, more wine and (I can’t believe this either) my first gelato. For a girl from Wisconsin who grew up with a milk addiction, this was a truly transcendent experience.

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Perfectly cooked al dente, chewy, homemade pastas and the magical gelato

The following day, we thought we’d channel our inner daredevils and rented Vespa scooters. We envisioned a picturesque jaunt through the hills, picking up some meats and cheeses and having an Instagram-worthy picnic day. What we did NOT know is Vespas are as heavy as motorcycles, difficult to navigate and, considering the language barrier, we would have to guess on our own how to ride. It was less than three minutes before I nearly took out an entire café, and we decided it better safe than sorry before one of us ended up in an ER in a foreign country. The Vespa dream died quickly, and that's okay.

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They look less menacing than they really are, as if to say "come on, take a ride - it'll be totally safe!"

Our short time here came to a close, but not before realizing that taxis do not exist in Cortona when it was time to head to the train station. Lesson learned, but we made it and took the two-hour trip back to Rome where more friends from Chicago arrived.

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Views from the top of Cortona, overlooking the valley with the Parco Regionale del Lago Trasimeno in the background

The Colosseum, Pantheon, Spanish Steps, Trevi Fountain, Vatican City, beautiful piazzas, a golf cart tour and, you guessed it, more wine, pasta and gelato to come.