The passion for the Bel Paese has accompanied Olivia Windsor since childhood. Today, the Australian entrepreneur organises food and wine tours exploring the Italy’s regions for small groups.
Where does the love that can drive one to take actions that might seem crazy, like leaving Australia to start a new life in the Bel Paese, come from? Sometimes it arises from a chance encounter, other times from a movie or a book, or perhaps from an exhibition attended simply to pass the time.
But sometimes that love is born at school, through interactions with childhood friends, through curious and attentive observation of what is different. And that’s exactly what happened to Windsor, who six years ago decided to leave her quiet life in Melbourne to embark on what was supposed to be a one-year adventure. Small spoiler: that’s not quite how it went.
Since she was a child, Windsor has always nurtured what she defines as a “certain fascination with Italy”. This is largely due to attending Catholic school, an environment where she not only studied Italian, but also grew up closely with many Italian-Australians, appreciating their culture and customs.
“Many of my schoolmates were Italian-Australians and that intrigued me a lot,” she recalled. “Often they would let me taste foods that were completely new and special to me: salami, olives, pasta … at my house we’d eat those things occasionally, but not as often nor prepared the same way.
“Even the stories of families making homemade tomato passata fascinated me. Food was definitely the first aspect that drew me closer to Italy.”
In Melbourne, Windsor studied communications and worked for several years in digital marketing and advertising for a well-known makeup company. However, even though her career was going quite well, she felt that it wasn’t her path.
“I had a great passion for food, wine and of course for Italy,” she said, “So I thought I’d give myself a year there, kind of as a life and work experience.
“Some of my friends had already lived similar experiences, in England or elsewhere. I had taken part in a cultural exchange program during my studies. So, I said to myself, ‘I’ll try a year in Italy, get by with some work, improve my language skills, maybe enter the world of food and wine and then I’ll go back home.’”
Windsor never went back home. In fact, today Italy is her home.
As her first stop, Windsor landed in Bologna in was May 2019. There, she had found a language school that offered the possibility to live with an Italian family, allowing for a true cultural exchange.
“It wasn’t easy, especially with the language. Before leaving, I had taken an Italian course for a year in Carlton, but when I arrived in Italy, I realised I could barely speak,” she revealed.
“During my months in Bologna, I was forced to speak Italian all the time. I went to school in the morning and in the afternoon continued speaking Italian with the host family. It was very demanding, but also very useful,” she added.
After the experience in Bologna, which lasted a few months, Windsor chose to join WWOOF (Willing Workers on Organic Farms), a program that offers the chance to work in agritourism, wineries or organic farms in exchange for food and accommodation.
Thanks to the program, Windsor explored parts of Tuscany, Umbria and Piedmont, and it was there that she met Andrea, the man who would later become her husband.
The wedding of Olivia and Andrea in Italy. (Photo: Rhianna May)
“At first, when I left, I thought it would just be for a year, but then I fell in love with both the country and my husband,” she shared.
“Italy is very different from Australia. The sense of community, the piazzas, the food, the art … I really loved all of it.
“Of course, the bureaucracy and some practical challenges aren’t easy, but the quality of life in terms of culture and relationships won me over.”
The opportunity to turn her dream into reality came a little later, when Windsor met Kate Clark, an Australian who runs a podcast called Untold Italy.
After collaborating on a special episode dedicated specifically to life in Piedmont, their friendship grew and led to a shared project: Untold Italy Tours, an agency specialising in food and wine trips for small groups of mostly Australians and Americans.
Untold Italy Tours organise gastronimic experiences for small groups. (Photo: Rhianna May)
Windsor handles the itinerary planning, developing complete packages that meet the needs of every traveller, combining art, culture and gastronomy. She doesn’t rely solely on her personal experiences, which have taken her to travel and work across many Italian regions over the years, but utilises third-party resources.
“I also include online research and guides like Osterie d’Italia, then I make use of the contacts I have thanks to the podcast and go visit places myself: wineries, cheese producers, restaurants, artisans…,” she explained.
“We offer complete packages with accommodation; culinary experiences and cultural activities like cooking classes or visits to museums and historic palaces.”
A tour in Apulia. (Photo: Rhianna May)
Today, Windsor lives in Rome with Andrea and their first child. In addition to the Untold Italy Tours project – which next year will be enriched with a new package dedicated to Capri and Ischia, including a collaboration with an Australian chef living in Capri who holds cooking classes – the entrepreneur has also launched a personal blog about life in the Bel Paese and Italian Wine Tales, a website dedicated to Italian wines, developed together with her husband after they completed a sommelier course in the capital.
Dining and Cooking