“I left Toronto to renovate a 16th-century Tuscan villa. Now, I host retreats here”

When British-Canadian TV personality Debbie Travis and her husband, Hans Rosenstein, took their production company, Whalley-Abbey Media, abroad to film the third season of Debbie Travis’ Painted House, they fell in love with Italy and started dreaming about owning property there. After eight years of searching for the perfect place, they spent seven figures converting a ruin on a Tuscan hillside into their dream home and a boutique hotel for all-inclusive retreats. Here, Travis tells us how they did it.

I’ve worked in television all my life, first in London in my 20s, then in Canada after I married my husband and moved with him to Montreal. I taught myself how to do paint finishes and was quite good at it, so in 1993 I decided to make a VHS video teaching people how, which inspired Hans and I to put together a small crew and launch our production company, Whalley-Abbey Media, with Decorative Paint Finishes Made Easy with Debbie Travis.

In 1995, the Women’s Television Network asked me to turn the concept into a TV show, and we created Debbie Travis’ Painted House, one of the first decorating shows in North America. I did another four shows after that, had product lines with Canadian Tire and wrote a dozen books about interior decorating. Though we filmed in Montreal and parts of the US, all of the English programming was headquartered in Toronto, so we were constantly travelling here for meetings. Finally, we moved here and bought a condo on Soho Street just off Queen. We still have it, and I love it.

As Whalley-Abbey Media grew, we started to film abroad. When we went to Italy, we were totally inspired by all the ancient stencils, faux marble and frescoes. Hans and I were gobsmacked by the beauty and way of life there, and we started dreaming of buying a holiday house in Italy. We didn’t have enough money at the time, so we started to rent properties instead. We’d go on family vacations once a year and scout around for potential homes. Then, one day in the late 2000s, I was being interviewed onstage at an event, and she asked, “What’s next for Debbie Travis?” Suddenly this vision came to me and I started spouting it off, fully making it up as I went. I said, “I’m going to invite people to my Tuscan villa, and we’re going to do yoga in the lavender field. We’re going to hike through the olive groves, and we’re going to drink beautiful Tuscan wine.”

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The room went quiet. Then the lights came on and there were 1,000 women staring at me. And I thought, Have I bored them to death? Suddenly all these arms shot up, and people shouted, “Take me! Take me!” I realized I liked the idea of running some sort of business in my holiday home, but I didn’t want it to be a hotel. By then we were doing well, so I changed my idea from a family holiday home to an ever bigger place that could host guests as well.

Buying property in Italy is very different from buying it in Toronto—the good stuff isn’t really online. It’s all word of mouth—you know, the butcher’s mother’s uncle’s friend. So you get to know properties by really spending time there and getting to know the locals. And you have to get to know them, because these old farms are often owned by many people, upward of 20 relatives, and everybody has to sign off on the sale.

We saw many properties, including old convents, farms, castles and even a building with train tracks running through it. There was one particularly derelict convent that had a very strange feeling in the air. There was no electricity, so I was using a flashlight, and when I entered the first room, there were stacks of human skulls and bones against the walls. I realized I was in a crypt. My agent said, “Oh, but you’re a designer—you could put a nice thick piece of glass and some nice lighting and it would make a marvelous dining room!" I flat-out ran out of there.

At another property in Puglia, we climbed over a wall, and Hans said, “I think I’ve been bitten.” By the time we left, his arm was the size of a sofa cushion—he’d been stung by a scorpion. We had to go to the hospital and get a cortisone shot.

Finally, we started to hone in on a particular region in Tuscany: a smaller valley running off the grand and famous Val d’Orcia, which is a UNESCO Heritage Site. We found a beautiful B&B and stayed there several times as we searched for homes, but many of them were ruins. Then one day the owner of the B&B called and said he’d heard of a property for sale called Villa Reniella.

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I was busy filming in Toronto, so Hans flew over to check it out. This was December of 2010. He called me immediately and said, “Well, I finally found it, and if you don’t like it, I’ll marry somebody in the village.” I wasn’t worried—the average age there is about 85.

It was another three months before I could get to Tuscany to see it. The day I arrived, it was pouring rain. I was exhausted and there was mud everywhere. The main building was a villa from 1600 that had previously been a lookout tower. It was on top of a hill on a run-down farm, and it was a total wreck. There was a barn with three and a half floors. Parts of the roof were missing, and there were trees growing out of it. Then there were pigsties with pigs and chickens running around and sludge everywhere. I had to jump over a river of poop coming out of what’s now my living room.

I hated it, and I felt like I’d come all that way for nothing. We had a bit of a marital row that night, but Hans convinced me to go back and look once more. And sure enough, the next day, there was this beautiful blue Tuscan sky. I looked across the valley, and I saw the potential. I just wanted to weep.

I hadn’t really wanted anything this size—it’s almost 11,000 square feet on 100 acres of land—and I certainly didn’t want a ruin. But that view! As I stood there in awe, the agent said, “I’ve seen your television show. You can do anything.”

Well, not this, I thought, but suddenly I was on a mission. We signed on the dotted line right then and there.

Hans went back to Toronto, and I stayed to oversee the groundwork. The plan was to rebuild the lookout tower and restore the main villa for us to live in and turn the pigsties and barn into guest suites.

I rented a place nearby so that I could host my first retreat while the property was being restored. When we began renovating, I slept on a mattress on the ground floor of our villa, which still had some trees growing through the roof. There was a rudimentary bathroom that had been used by the farmers who lived there previously, and it was a lovely summer. For a long time I was walking around with a candle. I had a little camping stove so I could heat up food.

The first thing we did was get a project manager who spoke English, and then we got an architect. The first six months were very difficult because the workers weren’t used to doing business with a woman. At one point we had 80 guys here, and they would say, “We’ll wait for Mr. Hans to wake up in Toronto time.” It was driving me insane, and finally I couldn’t take it anymore.

We had a beautiful fig tree, so I got these two fat, juicy figs, and I called all the men over and said, “These are your testicles, and this is what I’m going to do unless you start talking to me.” I squeezed, and the juice dribbled down my arm. I never had a problem after that.

The real work started about a year in, when the barn and the pigsties were demolished and we began rebuilding. Once the roof of the villa was removed, I started renting an apartment in Montepulciano, a medieval town across the valley. That was for 18 months, and when the villa was restored, I moved back in.

By this time I’d been working in Canadian television for 20 years, and it just wasn’t exciting me anymore. But I never wanted to retire, so I decided to commit myself to the renovation and the retreat business. For the next five years, I lived on the property almost full time to finish the renovation. I would take language classes in the morning, race back at lunch and call Hans in the evening to explain what was going on and vent any frustrations.

The property is a heritage site protected by UNESCO, so there are many rules: you can build only where there were buildings before, you can’t change the roof line, you can’t put in a blue plastic swimming pool liner because the government doesn’t want it to look like you’re flying over Florida from above. The intention is to preserve the natural landscape as much as possible.

I think there were 27 permits that we had to fight for. I was convinced that the woman in the local permit office hated me, and sometimes I felt like she was watching out of the window when I arrived, ready with her “No” stamp. If she said yes, the request got forwarded to Siena, where the main office for this part of Tuscany is located, for a final sign-off. If we didn’t hear back after two months, it meant we could move ahead. So I was constantly praying that no letter came.

Of course, they said no to many things. My idea of a villa was plastered like you’d see in Venice, but the permit office said no, it had to be the original butter-coloured stone. That’s because our valley had been inhabited by poor farmers who couldn’t afford plaster, and the authorities demand that you keep renovations in the style of the area. Now, though, I thank god I didn’t use plaster, because the stone is so much more natural looking.

We reused the wood pigsty doors as headboards in some of the rooms, and we bought a great deal of recycled antique beams, tile and stone. Inside, we added modern technology—now water flows under the floors, which are large slabs of ancient stone, to keep them temperate: warm in the winter and cool in the summer.

We also had to put in a well for more water since we have 16 bathrooms and 100 acres of land to take care of, which was very costly. Water is scarce for half the year due to Tuscany’s long hot summers, so extra water needs to be stored for those dry months.

I had to buy all the furnishings and fittings for 14 bedrooms, four living rooms and two kitchens, and I decided to get the best designer items: modern pieces from companies like Dedon, Paola Lenti, B&B Italia. The beds are all handmade metal four-posters, but I added vintage pieces like mirrors, ladders and benches that I collected from antique markets across Europe.

Then we had to deal with the landscaping. It was just mud apart from the existing olive trees—I think there were about 1,800 trees when we first moved in, and now we have 4,000. We make great cold-pressed olive oil, Debbie Travis’ Organic Olive Oil, that we sell across North America through my website.

In the end, the whole project cost us seven figures. It could have gone on forever, but we had a deadline because I had a retreat booked for June of 2015. I was so excited—I had filled that retreat before we even had a roof. Toward the end, the deadline felt just like working on a TV show, where you can have as little as four days to do a renovation.

When the first guests arrived at Villa Reniella, they were as gobsmacked as we had been when we first fell in love with Italy. Because I already had an audience from TV, I was able to fill up the whole summer. When they arrive, some guests sink to their knees and others burst into tears—they’ve booked this trip a year in advance and have been dreaming of it for so long, then they see the landscape and know it’s going to be a week like no other.

We now offer several different week-long retreats starting at about $9,000 per person, like the Tuscan Girls Getaway or the Classic Car Rally Retreat, where our guests can spend their days driving iconic cars along scenic routes and return to the villa for food and wine. The cars are supplied by a company in France, and we have a fleet of 50 vintage beauties to choose from, including Ferraris, Mercedes, Jaguars, Porsches—you name it!

I love living here. I’ve found it easy to make friends because there are a lot of expats. The food is amazing, local and fresh, and I keep active because we live on a hill and we’re always walking back and forth. I feel healthier than I did 15 years ago.

When people leave here, they always say, “But I’m going back to my condo in Toronto. How do I continue to feel like this?” The thing about Tuscany is that it’s a time warp—people live like our grandparents lived. They see their friends, they spend time outside, they make jam and tomato sauce. In 2021, I wrote a book called Joy about everything I’ve learned from Tuscan living, and I have a new book coming out in October called Laugh More: Stories From an Unexpected Life, about the funny things that continue to surprise me here. Like one day when I got so lost driving that I had to stop on the side of the road. There was an old man walking along, and he just hopped in the back seat! If that had happened anywhere else, I’d have called the police. But he just said, “Go, go.” So I showed him the place I was looking for on the map, and he directed me there without a word, then just got out. I was left sitting there on the side of the road, thinking, What just happened?

Looking back on the renovation, I wouldn’t change a thing even though it was so much work. I think it’s a bit like having a child—if you remembered every detail of the birth, you would never do it again. So now I just see the glory of it.