Italian for Beginners

In 2000, we were a typical New York media couple. I worked as a travel editor, always on the hunt for the next hot destination, while my future husband, John, a record label executive, chased stars like Christina Aguilera and the Foo Fighters around the world on promotional tours. We worked all hours, and every once in a long while, enjoyed a night with no plans in our cute studio apartment in Brooklyn. We were happy but exhausted.

Less than a year later, our search for a wedding venue took us to Tuscany, a golden place where I had lived as a kid up until my father died. We finally found our venue (the private vineyard of Castello di Argiano outside Montalcino), but it had been hard to locate the perfect spot: Gorgeous villas didn't have enough services; beautiful hotels were too formal or lacked personality. One night, after a long day of exploring and more than a little wine, I could see John's marketing side churning. "What this region needs is a small, stylish hotel in an incredible location. What if we did it ourselves?" Surely a lot of people who have reached the bottom of a Brunello bottle on a starlit Tuscan night have said the same thing. The crazy part is, we actually did it.

I was terrified in ways that I couldn't even articulate at the time. It had taken years to recover from my dad's death, and my British mother's move to New York had been difficult. I had only recently come to think of the city as home with a real support system. Plus, moving meant truly committing to someone and taking a big gamble on the future. (I realized later that I had always made an emotional escape hatch for myself after losing someone so close, so young.) At the same time, I started to feel that our fast-paced New York life wasn't making me happy. Could the Italian countryside be the idyllic place it had once represented—without my dad but with my own family?

After three years scouring the picturesque farmland between Pienza and Montepulciano, we finally found our hideaway: a crumbling shell of a 1920s farmhouse called La Bandita, with cows camped out in the future living room and two pigs where we imagined the suite would be one day. There was no electricity or plumbing, not a single tree, and plenty of legal knots. But the spot had an epic 360-degree view of the UNESCO site Val d'Orcia, inside a protected nature reserve, and was a short drive to our favorite villages of Pienza, Montepulciano, and Montalcino. Most of all, something about the land made me feel safe and at peace, which was strange, considering we had just put our life savings (and the trust and investment of a dear childhood friend of John's) into a pile of rocks up a bumpy road. Our only credentials were that we loved hotels. John had never changed a lightbulb, but he knew about taking care of high-maintenance clients. (B12 shots for Xtina in the middle of the night in Madrid? No problem!)

The construction process was at times horrifying. When setbacks happened, I struggled, sometimes unsuccessfully, not to blame John for moving us from our comfort zone. I remember a particularly bad fight one night—I can't recall whether it was about planting just olive trees or olives and oaks, or about the light switches—but I left the house crying and walked to the little country church that was one of my favorite places. I put my hand on the massive antique door and thought, We didn't move here to have our relationship fall apart over ridiculous design details. We moved here to have a different lifestyle, to have a family, to support each other in different careers. Something deeply shifted in me after that, and unless an issue was monumental, I didn't care as long as we were healthy and intact. I still feel that way.

The morning after our first guests left La Bandita, we swam in the infinity pool (it took two years to get permission to build it), relaxed in the Turkish steam room, then took baths in two of the rooms. Just because we could. We owned a hotel in Tuscany with a pool!

After that first insane year, things settled into a more livable routine. Now, instead of taking the crammed subway to Times Square, we walk to a café opposite the Renaissance cathedral before I go to my home office on a medieval alley to write. I know at least by face, if not name, the 2,000 residents of our town, where my 3-year-old blond son, Jacopo, is basically a local celebrity. I once worried that I would feel isolated here, sitting in a park with no other new moms because of Italy's notoriously low birth rates, but 23 babies were born in Pienza in 2010. Along with those moms, I made friends with an architect with two daughters, a transplant from Milan, two sisters in their 20s, and a Polish woman who first looked after Jacopo before becoming my confidante.

Our life is not a rejection of New York. Some of our dearest friends are there, and we visit at least twice a year. I miss walking over the Brooklyn Bridge, my yoga studio, sushi, diner food, impromptu cocktail dates, and the diversity of the people. But our lifestyle now is of a different caliber than we could ever have had there.

We've just opened our second project, a 12-room hotel called La Bandita Townhouse, in a 16th-century former nunnery in the town of Pienza. In hindsight, the risks and the unknowns we took 10 years ago all seem worth it. But the process involved a great deal of stomach-girding faith. I was pushed in many ways to make the jump, but confronting that fear made me realize how taking gambles empowers you to make the changes that lead to greater happiness. And you never know what things from the big city will arrive in Pienza. A juice bar opened around the corner from the new hotel, and I have just come back from my first Zumba class at the community center!

"Moving meant truly committing to someone and taking a big gamble on the future."