Women Rebuilding Tuscany: Inspiring Stories of Entrepreneurship, Travel, and Italian Dreams
Dreams of Italy – A Women’s Experience - this is an article I published in a local magazine in 2009 - but the memories and truths still hold. Enjoy!
Tuscany, Umbria, Piemonte—names that evoke visions of cypress-lined roads, ancient monasteries, hilltop towns, exquisite food, and world-class wines. Campania, Sicily, and the Cinque Terre, with their seaside villages and terraced hillsides—Italy is a dream, a destination at the top of countless travel lists. And for many, renting a villa in Italy is the ultimate aspiration.
To help fulfill that dream, I traveled to Italy. A former international banker, I had grown tired of long desk-bound days. As one of the early female graduates of the Richard Ivey School of Business—when only 5% of the class were women compared to nearly 50% today—I had been led to believe that we could "do it all, have it all, and be super mom, wife, and professional." That myth fractured over time. Three children later, I traveled to Italy to explore a business opportunity for a client. Though that venture didn’t work out, I discovered something even greater: a passion for Italy—the people, the food, the Renaissance towns, the countryside, the farmhouses. But what inspired me most were the women I met—women who are redefining and rebuilding Tuscany.
Women Rebuilding Tuscany
I met incredible women who had not only chosen Tuscany but were reshaping its landscapes, businesses, and hospitality.
- Katharine, an American expat, embodies the real *Under the Tuscan Sun* story (she even vetted Bramasole for Frances Mayes before she bought it). She found a ruined estate on a hilltop near Cortona, on the Tuscany-Umbria border. The three houses that now stand there are breathtaking, with ancient beams in the bedrooms, stunning headboards crafted from 100-year-old wooden doors, and wrought-iron ‘ferro battuto’ side tables that resemble freshly picked flowers.
- Ilaria, young woman whose father helped her purchase an ancient monastery, scoured the antique markets of Arezzo to find just the right pieces. She studied the history of the building and blended traditional herbal scents into the hallways, crafting a magical ambiance.
- Ilaria, the Contessa, has an impeccable eye for interiors. Alongside her husband, she has transformed villas throughout the Val d’Orcia. Designing her own furnishings and décor, she now owns a unique boutique in the heart of Rome, her work frequently featured in *Travel & Leisure*, *Gourmet*, and European design magazines.
- Dominique, an art collector and designer, revived the ancient Tuscan linen wall-finishing technique in the restoration of her farmhouse, staying true to tradition with remarkable precision.
- Elisabetta, an expat from California, immersed herself in Italy’s culinary world. With her business partner, Melchiore, she runs delightful villa-based cooking classes, bringing authentic Italian cuisine to travelers. ( 2009) - Now she has published successful books about the food culture of Umbria, and continue with her food related journey.
- Cinzia, an exceptional businesswoman, elevated her Relais & Châteaux property to new heights, offering unparalleled service and quality.
- Donatella established a trailblazing winery run entirely by women—an extraordinary feat in the male-dominated world of Montalcino wines.
- Lucia sold her share of the family olive oil business to create a stunning *borgo* estate, a walled sanctuary housing just six unique apartments. The setting—golden stone buildings, vibrant red geraniums, white roses, lavender—became the backdrop for an unforgettable mother-daughter trip, captured beautifully in a newly bought Florence dress.
So many women, so many stories. My journey to find unique and special properties introduced me to these extraordinary women and their ventures. I want the women of Canada and the USA to experience Italy and find a way to bring Italy home.
Women Traveling Together – A Growing Phenomenon
Women traveling solo or in groups has become a well-documented trend. More women than ever are choosing to travel alone or with friends, sisters, mothers, or book clubs—whether to celebrate a milestone birthday, heal from a personal loss, achieve a long-held dream, or simply take a well-earned break from daily life.
Dr. John Gray, author of *Men Are from Mars, Women Are from Venus*, explains that there is even a physiological component to this:
> "Oxytocin is the bonding hormone, and research shows that oxytocin is the primary hormone in a woman's body responsible for helping her cope with stress. Friendships between women stimulate oxytocin, as women tend to nurture each other when they travel together, particularly on girlfriend getaways."*
This phenomenon, combined with Italy’s inherently warm and welcoming culture, makes the country an ideal destination for women travelers. The Italians are naturally generous, helpful, and inviting, making solo travel easy and enriching.
A Memorable Solo Travel Experience
The first time I went to Italy, I traveled alone. I had no prior experience in the country and spoke no Italian. One evening, while driving on a dark country road, my tire went flat. With only a tiny dictionary in hand, I looked up the word for “tire” and ventured toward a small, dimly lit hut nearby. Two men inside, engaged in deep discussion, gestured down the road when I attempted to explain my predicament.
Following their direction, I soon found a car dealership, where a mechanic was still at work. I tried to communicate—"*La gomma è kaput!*"—and clapped my hands together to signal "flat." He nodded but spoke rapidly, believing that the louder and faster he talked, the more I would understand. Frustrated, I finally called Massimo, the owner of the *agriturismo* where I was staying. We had only met that morning, but he told me to wait—he’d be right there. Within 30 minutes, he arrived, negotiated with the mechanic to repair the tire that night (cash only, of course—no receipt possible), and followed me back to my room.
When I closed the door, the stress of the night hit me, and I cried. A few minutes later, there was a knock. Standing there was Massimo, holding two eggs, half a loaf of bread, some cake, and an apple. That small gesture of kindness encapsulated the generosity of Italy.
Embracing the Italian Dream
Italy is more than a destination—it’s a way of life. It’s about taking time to savor a meal, to admire the light over the hills, to embrace friendships old and new. The women I met in Italy, whether locals or expats, are living their dream, restoring homes, crafting wines, building businesses, and welcoming others into their world.
And for those dreaming of Italy—whether to visit, live, or just carry a piece of it home—the journey is always worth it.
Also in CVV lets you know
Dolomites Last minute; Experience Luxury in the Dolomites: Your Ultimate Ski Getaway
Dolomites! Experience Luxury in the Dolomites: Your Ultimate Ski Getaway at Chalet Cipi
If you’re dreaming of an unforgettable winter escape, look no further than Chalet Cipi, a luxurious ski-in/ski-out chalet nestled in the breathtaking Dolomites. Available for a **limited time** from **January 11 to January 25**, this exclusive property is being offered at a **discounted price**, making it the perfect last-minute getaway for ski enthusiasts and luxury seekers alike.
For a limited time, **Chalet Cipi** is available at a discounted rate for bookings between **January 11 and January 25**. This exclusive opportunity won’t last long, so act quickly to secure your spot in this winter paradise.
Family Villas Tuscany
Explore Italy's Most Stunning Train Journeys: A Perfect Villa Escape Add-On
Explore Italy's Most Stunning Train Journeys: A Perfect Villa Escape Add-On
Italy is a country of endless beauty, where every corner offers a story, a flavor, or a view that takes your breath away. While staying in a charming villa offers the perfect base to immerse yourself in la dolce vita, adding a scenic train journey to your itinerary can elevate your Italian experience even further.
In a recent article by AFAR, some of the most picturesque train rides in Italy were highlighted, showcasing routes that take you through dramatic coastlines, rolling countryside, and even across to Sicily. Here are a few highlights to inspire your next trip:
© 2025 Classic Villa Vacations & More, a division of Classicvacationrental.com. Classic Villa Vacations & Experiences is a division of Classicvacationrental.com. Designed by Out of the Sandbox. Powered by Shopify
