Three Wrong Trains, 50 Euros and 20 Years in Italy Magic Towns Italy tells the story of how our founder, Jesse Andrews, turned a summer job in Calabria into Italy Vacation Specialists.
She came for one summer in 2003 and never left. Today the knowledge she gathered on foot, by bike and town by town shapes every trip we plan.
Our Story, Told by Magic Towns Italy
The story of our founder, Jesse Andrews, and more than 20 years of showing travelers the Italy most people miss.
Magic Towns Italy, a publication for people who dream of living in or moving to Italy, profiled our founder in its Expat Stories series. Writer Anna Costa sat down with Jesse for an honest look at how Italy Vacation Specialists came to be, from the very first day in Calabria to the company we are today.
She came for one summer in 2003 and never left.
It Started With Three Wrong Trains
A summer teaching job, 50 euros and a seaside town that was barely on the map.
In 2003 Jesse left Canada for a teaching job in Praia a Mare, a town of about 5,000 people in Calabria. She took the wrong train three times and arrived after dark with 50 euros in her pocket. The next morning she woke up to the Mediterranean and a row of palm trees.
Teaching was not her calling, but the town was. She stayed, started one of the early English-language blogs about Italy, and persuaded the local mayor to fund a website introducing Praia a Mare to English-speaking travelers. That one project opened the door to hotels, guides and small communities across the South that had no presence online at all.
When we recommend a village, a road or a family-run agriturismo, it is because one of us has been there.
Knowledge Earned on Foot and by Bike
Hundreds of towns documented, and a commitment to protecting the places we share.
The agency grew piece by piece, never from a business plan. Jesse worked as a hiking guide in Cinque Terre and on the Amalfi Coast, and as a cycling guide in Puglia, Sicily, Calabria, Tuscany, Umbria and Veneto. That is still how we plan trips today.
Magic Towns also highlights Jesse's background in conservation and her support for agriturismo stays, electric vehicle travel and low-impact tourism. It is why our trips can include bird-watching in Venice, falconry in Tuscany and wildlife experiences alongside the great art cities.
“Forget the fear and try it.”
Why She Stayed, and Why You Should Come
Italy is slow, beautiful and sometimes frustrating. For Jesse it is home.
The feature does not hide the hard parts, from Italian bureaucracy to a renovation that cost twice what was planned. Jesse now lives in Stimigliano, a small hill town about 35 minutes by train from Rome, and she would do it all again.
If her story has you thinking about your own trip, tell us what you have in mind and we will build it around you.
