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A food and wine tour of Cortona

 Spending 10 days in Cortona earlier in the year slowed my pulse, captured my heart, opened my senses and perhaps increased my waistline, although hikes up and down hilly cobblestone streets worked off some of the pasta calories.

 Piazza del Comune ©Alberto Sadini courtesy of Hotel S. Michele

Located at the eastern edge of Tuscany, bordering Umbria and beautiful Lake Trasimeno, Cortona is an open-air museum unchanged over many centuries. It is a quiet and peaceful place, bound forever to Etruscan history with an aspiring eye to the future. Cortona is one of two dozen historically significant Tuscan hill towns ringed by rampart walls built for defense in ancient and medieval times.

Even though the center of Cortona is clearly visible upon approach by car or train, it is possible to get lost trying to navigate the web of winding roads that lace the hill. True confession: I’ve done that several times. With parking eventually settled, stunning views of the surrounding Val di Chiana and delights inside the walled city unfold with every step.


In Normal Times, Cortona continues to be one of Tuscany’s most important tourist and cultural destinations, attracting adventurers, musicians, artists and thinkers from around the globe. Excellent dining, shopping, exploring and learning opportunities sit in the sweet spot where tradition meets the twenty-first century.

Compared to better-known hill towns such as Siena and Montepulciano, Cortona was largely undiscovered and mostly under the radar until 1996 when Frances Mayes published her blockbuster book Under the Tuscan Sun. Suddenly, sleepy Cortona burst into the global limelight. Its allure reached visitors near and far, many of whom eventually became permanent residents.

The people of Cortona are warm and welcoming. This cuts across the entire fellowship of humanity in Cortona, whether people are cortonesi, expats who moved to Cortona, homeowners who are part-time Cortona residents, or visitors who make regular pilgrimages. Even the people who rent apartments through Airbnb and VRBO are exceptionally helpful.

In Cortona, there is something for everyone, and so many love stories that explain its allure. So many people who visited Cortona as a teenager or young adult eventually moved there—some immediately, others after thirty years or more. But the call of Cortona cannot be resisted forever, and those with Cortona in their destiny will find a way to return.

Where to eat in Cortona

 Antipasti, courtesy ofRalph Johnson

It is a welcoming gastronomic pleasure to experience Cortona’s restaurants. Four of them were so good that I visited each one twice. Without exception, the food was excellent. My friends and I dined happily on charcuterie served with the best bread ever, house-made pasta, truffles, Chianina—the prized beef of Tuscany—and of course Tuscan wine. All four restaurants are just steps away from piazza della Repubblica, the heartbeat of central Cortona.

Housed in the romantic thirteenth-century Palazzo Cattani, Ristorante La Bucaccia da Romano pays homage to the tradition of calling ancient palace storage cellars “holes” or “bucaccia”. Always animated and flirtatious, Romano Magi creates a festive ambience as if every night is a special occasion and every guest is a long-lost friend. Don’t forget to say yes when he offers a taste of limoncello or grappa at the end of the meal.


An authentic, traditional Tuscan dining experience, Osteria del Teatro is distinctive because of its warm, relaxed, yet bustling atmosphere. In the words of one fan on the restaurant’s Facebook page, “If you ever come to Cortona, skip everything and go straight to that restaurant.” I agree. Small spoiler alert: a peek inside the ladies’ room is an essential part of the Osteria del Teatro experience (for both men and women).

Locanda al Pozzo Antico Ristorante is a family affair. Chef Paola, husband Franco and son Gianni Fabianelli choreograph joyful experiences under the watchful eye of mamma Dina, who each day sits regally at her exclusive table to assess the happiness quotient of the family’s guests. During my two visits, happiness was 110 percent! Cheese fondue with truffles (for the table) is a must-order house specialty.

Massimo Olivieri and Daniela Ottonello run a sweet caffè that doubles as a coffee bar and pasticceria. The Caffè Tuscher menu is pure, the food is fresh—mom bakes cookies every day—and deeply comforting. Whether you order something as simple as a grilled cheese on crunchy Tuscan bread or a daily regional specialty, Caffè Tuscher personifies Cortona’s welcoming arms.

Wines of Cortona

Tuscan vineyards, photo by Kathy Merchant 

While Cortona is a relative newcomer to Tuscany’s quality wine offerings, it has two main assets. One is that the Syrah grape grows very well in Cortona, distinctive in a region dominated by the Sangiovese grape. Plus, Cortona’s great location is equally important with easy access to the other Tuscan wine regions, as well as the cities of Siena, Florence, Arezzo and Perugia.

Cortona DOC is the only appellation in Italy where Syrah is the star grape. The d’Alessandro family led Cortona’s rebirth as a top wine region starting in the 1980s and discovered that Syrah was the most suitable variety. The Cortona DOC was approved in 1999, paving the way for today’s group of 35 wineries producing over one million bottles a year, 85 per cent for the export market. While Cortona DOC wine labels currently say “Syrah,” soon labels will simply say Cortona,” like the French model, to honor the place where the grapes are grown.

Cortona’s favorite sommelier and wine retail shop owner, Marco Molesini, is a third generation cortonese. Each year, Molesini organizes a pilgrimage of international wine lovers to the Anteprime di Toscana wine preview events as journalists and trade professionals eagerly taste samples of Chianti Classico, Brunello di Montalcino, Vino Nobile di Montepulciano and Vernaccia di San Gimignano. In Molesini’s words, “Tuscany is the only place in the world where you can taste so many top-quality wines in just one week. It is a unique and special aspect of Tuscany.” 

The Molesini family story highlights opportunities that have drawn people to Cortona for many centuries. In 1937, Marco’s grandparents moved to Cortona from northern Italy seeking better economic prospects. They started a grocery and sold wine, a long-standing tradition in Italian markets. Marco’s parents joined the family business, followed by Marco and his brother Paolo. After becoming a sommelier, Marco decided with Paolo to grow the retail wine business. Today, Enoteca Molesini offers more than 1,500 labels of fine Italian wines, available for shipping globally.

In addition to Tenimenti d’Alessandro, Molesini recommends experiencing these four leading wineries in Cortona DOC: Stefano Amerighi, a leading biodynamic winemaker; Antinori’s Tenuta La Braccesca, a large farm known for honoring tradition while inviting innovation; Fabrizio Dionisio, a boutique winery producing only Syrah; and Fabrizio Doveri, a tiny producer of powerful yet elegant Syrah wines.

In her own words: Amore 

Sunset over Cortona and Val di Chiana ©Alberto Sadini

 

Author Frances Mayes isn’t the only Cortona lover. These stories from Julie (United Kingdom), Michela (Cortona), Karen (United States) and Hannah (United States/ Cortona) highlight the town’s allure.

Julie (United Kingdom): I had only been in Cortona three days (on my first visit) when I put in an offer on an apartment. I’d never been to Tuscany before, I’d never heard of Frances Mayes or Under the Tuscan Sun, and I wasn’t loaded with money. I just fell in love with Cortona and wanted to feel part of it rather than be a visitor. Three years later, I’ve sold my apartment and bought a house on the same street. In the UK, I live in a very pretty cottage in the Cotswolds, but I feel more at home in Cortona.


Michela (Cortona): I was born in England 32 years ago. My parents met and fell in love while they were working for a cruise line. My mum is British of Jamaican heritage; my father is from Cortona. For two years after I was born, he commuted to Italy for work until our house was ready. Mum was the only black lady living in this tiny village, so it was a shock for everybody when we arrived. (Let’s just say the cortonesi had something to talk about.) My childhood was 


safe, comfortable and connected. People often ask me why I stay in Cortona, a little village that looks like it doesn’t have anything to offer the young generation. I have everything that I need and want. I love my beautiful Cortona!


Karen (United States): Thirty-six years after my first visit to Italy, I now own a home in Cortona. My love affair started with a life-changing decision in 2013 to attend Le Cordon Bleu (in the US). I chose Cortona for my restaurant externship. To my surprise and delight, Osteria del Teatro’s chef/owner Emilio Rossi invited me to train with him for six weeks. I made friends from all over the world, a home away from home. People greeted me by name as I walked through town. I felt like part of their community. Now I’m a real estate agent, so I decided to look at properties for ideas, and possibly for a future purchase. As soon as I entered the house (that I now own), I felt at home. I love the street it is on, the beautiful wood doors, the curved staircase, the charming patio…


Hannah (United States): I was born and raised in Orange County, California. As a college junior, I had the opportunity to study fine arts in Cortona for a semester abroad. I travelled all over Tuscany, ate delicious food, drank beautiful wines, and met an incredible young man who convinced me to move to Cortona and who is now my husband. It was an easy decision. Off I went ten days after graduation. Coming back to Cortona felt like being hugged by a dear friend. People welcomed me with open arms. Today it is my home, and I adore everything about it, from learning new recipes from the veggie guy at the market to chatting with neighbors on the bench in front of my house.

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