There’s a certain kind of travel dream that lingers long after the trip ends, one rooted in rolling hills, shared tables, and a slower pace of life that feels worlds away from home. For Serena Kalen, that vision became something tangible through Isola Serena, a private luxury villa set in the heart of Chianti. What began as years of visiting Tuscany and searching for the perfect place to stay evolved into a hands-on restoration of a historic property, blending traditional craftsmanship with the modern comforts many travellers miss, and creating a destination designed for connection, celebration, and a true sense of escape.
What is your business called and what does it do?
Isola Serena, a private luxury villa in Chianti, Tuscany, that can accommodate up to 23 people, and offers a beautiful opportunity to explore Tuscany.
What made you want to do this work?
My husband fell in love with Tuscany over 20 years ago and travelled there every summer for vacation. When we started dating, he brought me to Tuscany for the first time, and I instantly fell in love with the beautiful rolling hill views, the community, the food, the wine and the culture. We rented villas every year, but there was always something that didn’t quite meet all the criteria we were looking for, and we decided our dream was to build and restore a villa ourselves and make it completely our own. In 2013, we searched property listings online and came across a farmhouse ruin that was part of a castle in 1077, and it had the most breathtaking views of the Tuscan countryside. We purchased it and started our Tuscan restoration journey to build our dream home, starting small, and expanding it year over year – as it now stands, Isola Serena is a world-class, private luxury resort and one of the largest villas in Chianti!
What problem did you want to solve with the business?
Many villas in Tuscany are hundreds of years old and have preserved their architecture and authenticity, but they lack the comforts of home we enjoy in North America. We wanted to build a villa that preserved Tuscan culture, artisanal traditions, and craftsmanship, while complementing them with modern amenities and furniture. With the most breathtaking views in the Tuscany countryside, Isola Serena has 1 main house and 2 guesthouses that include 10 bedrooms all with ensuite bathrooms and sleeps up to 23 people, AC/heating temperature-controlled -panels in every room, strong wifi throughout the entire property, a fully stocked chef’s kitchen, large infinity pool, small heated plunge pool, and more. This is very unique and special for luxury villa rentals in Tuscany, and it makes for a very comfortable experience for our guests to enjoy a week in the Tuscan paradise!
Who are your clientele/demographics?
The demographic skews older – 40s and above, families or large groups who are celebrating a special occasion, or we get a lot of big families looking for a comfortable getaway in Tuscany.
How does your business make money? How does it work?
As Toronto natives, my husband and I travel back and forth to Tuscany with our two young boys, but we rent the villa year-round when we’re not there. For 2026, the villa rents for $34,800 CAD per week in high season and for $28K CAD per week in low season. This year, we are already almost fully booked for the season, with only a couple of weeks remaining!
Where in the city can we find your profession?
We have a home office in Toronto where we are in constant contact with our Italian contractors, vendors, and partners who help operate and maintain our property overseas. We also handle all marketing, social media, bookings, partnerships, and client experiences from Toronto. We have a local Tuscan property manager on-site who checks our guests in and out and is available to them 24/7 while they’re there.
What is the best question a prospective customer could ask a member of your profession when comparing services? Give the answer as well.
Can you tell me why I should travel to Tuscany and what is unique about your villa?
Tuscany is one of those places, unlike anywhere else in the world, that will change you, ground you, and reset you. The villa is also located in one of the most charming towns, Castellina in Chianti, which is centred around community, slow living and an appreciation of the culture – the land, the food, the wine, the olive oil, and of course, the people. At Isola Serena, with the incredible rolling hills and 360 panoramic views, it’s a place to slow down, relax, and recharge all while having the modern comforts and amenities you enjoy from home, spending time with the people you love.
What is the best part about what you do? What is the worst part?
The best part: there is nothing more rewarding than having guests thank us for the best week of their lives and sharing how special the villa was and how they created memories they will never forget! It makes every hard or challenging moment worth it and is the reason why we share our home and do what we do.
The worst part: managing an Italian property from Toronto and dealing with all the trades and contractors to continually maintain the huge grounds – there is always something that needs fixing or updating, and it is home ownership on a completely different level!
What is your favourite joke about your own profession?
When people tell us we don’t need to work anymore because we own a Tuscan villa! The operating costs and work involved in running and maintaining such a large property, and ensuring we provide the best experience for our guests, are a 24/7, full-time, around-the-clock job!
Where can we follow you?
PAY IT FORWARD: What is another local business that you love?
Everist was founded by 2 women in Toronto who are close friends of mine, and it is a beauty brand that focuses on the first patent-pending waterless hair and body concentrates. Sustainability is their “why” and central to how they formulate, package and push beauty forward. Their products are amazing and fit a whole bottle of shampoo and conditioner into a 100ml, travel-friendly, aluminum tube – perfect for travelling to Isola Serena!
