English Not all great stories start with a carefully mapped plan. Some begin with €50 in your pocket, a teaching job in a town you can’t find on any map, and three wrong trains that somehow lead you exactly where you need to be.
That’s how Jesse Andrews’ story started back in 2003, when she left Montreal with an English degree, an MBA, and absolutely no idea that a summer teaching gig in Calabria would turn into two decades of documenting, protecting, and sharing Italy’s most overlooked corners.
First Steps in Praia a Mare
After graduating, Jesse found a university posting that offered a position in “Praia a Mare“, a seaside town in Calabria with about 5,000 people. She started doing some research, but all in vain – she couldn’t find information anywhere.
So, with a bit of fear, she decided to take the job anyway.
“The trip down was chaos” she laughs now. “I took the wrong train three times. After a long flight from Montreal, I took the train from Rome. It passed Praia a Mare and went straight to Scalea. Then I got on the wrong train again and ended up all the way back in Salerno.
By the time she finally arrived – with only €50 her mom had given her, which she refused to break – it was nighttime. She had no idea where she was. The ladies who welcomed her made caprese salad, showed her to her apartment, and that was that.
The next morning changed everything.
“I woke up and I was right across from the Mediterranean Sea. It looked like the Caribbean. There were palm trees. I thought, Wow. This is amazing.”
From Summer Job to Life’s Work
Jesse quickly realized teaching young, unruly kids wasn’t her calling. The school wasn’t planning to renew her contract after summer, and honestly, she didn’t want them to. But she decided not to leave Praia a Mare and started writing.
“I started writing about the town and the surrounding villages I was visiting. Essentially, I started one of the first blogs about Italy. I called it Italian Visits.”
She walked into the mayor’s office and pitched him an idea: give her money to create an English-language website promoting Praia a Mare to English-speaking tourists. He said yes and gave her €5,000. “At the time, it felt like winning the lottery” Jesse says.
That single project opened everything. She got to know businesses, hotels, sponsors. She visited towns and cities that had zero online presence – especially across the South. And because she was there at exactly the right moment, before the flood of travel blogs and influencers, her work filled a massive gap.
“Today that kind of opportunity wouldn’t work – there are too many blogs, too many influencers. But back then it was perfect timing.”
The result? Jesse ended up documenting hundreds of towns and cities across Italy – not just in Calabria, but throughout the South, Central, and Northern regions too.
Building a Business in Italy While Protecting Its Beauty
The travel agency didn’t appear overnight. It grew organically, piece by piece. Jesse went back to Canada and started working with travel agencies there, inviting people to visit the South. Meanwhile, her online content was attracting requests: transfers, guides, trip planning help.
She became a hiking guide in Cinque Terre and the Amalfi Coast. A cycling guide in Puglia, Sicily, Calabria, Tuscany, Umbria, Veneto – basically everywhere. The on-the-ground knowledge she gained from walking and cycling these regions became the foundation of what would eventually become Italy Vacation Specialists, now one of the leading travel agencies across Italy.
What sets Jesse apart from other competitors is her philosophy and love for nature. She’s not just showing people Italy – she’s actively working to protect it.
“I love Italy’s art cities – Rome, Florence, everything – but as a Canadian, nature has always been my passion. I studied conservation and environmental sciences, and Italy’s biodiversity is unbelievable – it is truly wild and beautiful. Documenting it has become one of my greatest passions.”
Along with Gregor Robertson, the mayor of Vancouver, Jesse has been leading environmental initiatives in regions throughout Italy. She’s been involved in projects like the Umbria Green Card, promoting agriturismi, encouraging electric vehicle travel, and supporting zero-impact tourism. Italy Vacation Specialists now offers experiences like bird-watching tours in Venice, falconry in Tuscany, and wildlife-focused trips across the country.
Moving On: From Calabria to Lazio
Despite her deep love for Praia a Mare, Jesse eventually decided it was time for a change. The town was absolutely beautiful, but she found herself struggling with the pace of development and the challenges of building sustainable tourism projects in a place heavily dependent on the summer season.
Jesse had tried to make a difference. She worked with local officials, created projects, organized events to promote the region. But between bureaucratic hurdles and the difficulty of getting initiatives off the ground, progress felt painfully slow. The lesson she learned applies to anyone moving to Italy:
“You can’t come here thinking you’ll change it. Either you accept Italy as it is, or it will break your heart. I didn’t want to become pessimistic, so I moved on to where I could channel my energy more effectively.”
She decided to settle near Rome, a city she didn’t like at first because of its chaos. So she escaped into the countryside and discovered the breathtaking areas surrounding the capital: Trevignano Romano, Bracciano, the Sabina. In fact, differently from what someone might think, the area around Rome is surrounded by mountains, vineyards, volcanic lakes, and near the Mediterranean Sea. Now she’s based in a small mountain town called Stimigliano, about 35 minutes from Rome Tiburtina station.
That focus on Lazio reflects Jesse’s broader approach: going beyond the typical tourist spots. Her website features an interactive map covering everything from Sicily to Trentino-Alto Adige, showcasing towns and cities in every region – content born from years of her traveling, living in, and documenting these places.
The Reality Check
Integration in a new country isn’t always easy, even if you’ve been living there for years – especially in a tiny town. But, as anywhere else in the world, you can meet both incredible and dishonest people. According to Jesse, one of the biggest challenges in Italy is bureaucratic inconsistency:
“Different people at the Questura will tell you different things. There’s no clear, consistent guidance. So you need to be prepared for that.”
In the different interviews we’ve conducted, this is a common theme. For this reason, what we always suggest – and what we’ve noticed makes a huge difference for those who do it – is not to move without a “squad” of people who can help you through all the different steps: from accountants to lawyers and beyond.
This applies to renovation projects as well (in this regard, we’ve just published a free ebook: “The Ultimate Guide to Buying and Owning Property in Italy”). Another challenge Jesse mentioned is being conscious of renovation times and costs, because what at first might seem like a bargain can hide lots of unexpected expenses:
“We bought a unit for €50,000, thinking it was a bargain, but between renovations, unexpected problems, and windows costing €15,000, we spent double. Workers told me: ‘Next time, buy a place where the windows already exist.'”
Why She Never Left (And Why She’d Do It Again)
So after all that, what made Jesse fall in love with Italy and decide to build a life here? It’s the pace you breathe every day, along with the fact that it’s safer and definitely easier to save money:
“When I go back to North America, everything feels ‘go-go-go.’ People work like crazy just to survive. A studio apartment in Vancouver costs over $800,000. Most people work 9-5 and still can’t save. Groceries there? A small bag is $100. Here, €20 buys incredible food. The quality is outstanding.”
For Jesse, Italy gives her something essential: “I wanted a life where I wake up and feel awe. Italy gives me that“. Her team, her suppliers, the people she’s met along the way: “They’re my family now. It’s not just food and wine – it’s a deeper sense of belonging, beauty, and inspiration. The truth is that everywhere has its ‘hard.’ You choose the ‘hard’ you can live with.”
Jesse’s Advice: Forget the Fear
If you’re reading this and dreaming of making a similar move, here’s what Jesse wants you to know:
“Forget the fear and try it. You can always go back. The worst thing about fear is the fear itself. So I accept the challenges as they come. And the alternative – North America’s cost of living and stress – doesn’t appeal to me. Italy is slow, beautiful, sometimes frustrating, but also inspiring. It’s home.”
She suggests coming for a year first, taking language lessons, and experiencing life here before investing in property. And remember – you can find support online, communities of people who’ve walked this path before you.
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