Simple Italy

Our group will enjoy the amenities of the Montestigliano Estate near Siena.

Please Join Us For a “Celebration of the Senses”

Tuscany is filled with magical places. Places that inspire awe, surprise you with their beauty, link you to the seasons, nature, and the rich heritage of Italian life, laughter, art, food, and wine.

But few Tuscan locales offer the splendid seclusion, the golden patina, and the warmth of Villa Pipistrelli where we invite you to indulge your “Inner Italian” with us next April.

Like the richness of a Sassicaia Super-Tuscan vino rosso, we’ve blended a unique combination of off-site adventures, on-site experiences, guest experts, authors, and the luxury of free time to inspire you to look at life in a fresh way. You will see, taste, touch, smell, and hear Tuscany instead of being isolated behind the windows of a massive motorcoach.

Our “family” of 14 travelers will unpack only once, settle in, and call Villa Pipistrelli home. The Donati family, who own and steward the estate, tell us that guests have been known to cry when they say goodbye to Villa Pipistrelli. Seriously!

We hope this adventure will feel like an expanded version of the liveliest dinner party you’ve ever attended. . . here’s the menu for our feast, the Complete Tour Itinerary.

–Sharon and Walter

Author Jennifer Criswell and Cinder.

By Sharon Sanders

Jennifer Criswell had guts.  She wasn’t rich. She wasn’t fluent in Italian. And, she was no longer of the age where people say things like, “Oh, she’s young. . . she’s just finding herself.”

Yet, she moved from New York City to live in Tuscany. As a local barrista quizzically asked when she told him she was living in Montepulciano: “Ma, per sempre?” (but, forever?)

Her companion was a beloved Weimaraner named Cinder who, as you might suppose, was also neither rich, fluent in Italian, nor a frisky pup. 

In At Least You’re in Tuscany: A Somewhat Disastrous Quest for the Sweet Life, Criswell shares the transformation with candor and humor. By her own admission, “It certainly wasn’t the sensible thing to do.”

Ten years before relocating, Criswell experienced an epiphany in Pienza, the last stay on her first trip to Italy, a three-week jaunt through the peninsula. Confiding in her journal, she realized that she no longer wanted to be a lawyer. She wanted to be a writer, and, more importantly, she wanted to be a writer in Italy.

Although her resolve was firm, the move was not fast. She writes, “My dream of Tuscany inspired me to start making changes. It took nine years, a move from Miami to New York—where I survived (just) as a dog walker on the Upper West Side—loads of Italian lessons, and three more trips before I hoisted sail on my Italian odyssey. But when you’re meant to be somewhere, everything in between feels like you’re treading water, just waiting for that wave to lift you and carry you onto the shore of your new land. My new land was Italy.”

Read more about Jennifer's avventura.

 By Walter Sanders

John and Peggy Heywood take a break from hiking in the hills surrounding Montestigliano.

There are magical places on earth. Places that revive happy memories and help you create new ones. Places that inspire great activity and make you feel productive, welcome, and alive.

For John B. Heywood, Sun Jae Professor of Mechanical Engineering Emeritus at MIT, Tuscany is that magical place. More specifically, it’s a hilltop agriturismo hamlet just south of Siena called Montestigliano.

“This whole Italy thing began about 20 years ago, when my wife Peggy and I saw a film called Enchanted April,” John says.

“We were captivated by the movie. It portrayed how a group of British visitors were transformed during a trip to Italy,” Peggy says. “We tried to figure out how we could incorporate Italy into John’s work as well as our personal lives.”

The answer turned out to be a sabbatical.

Read more about MIT to Tuscany

This article first appeared in the October 2012 issue
 of the award-winning subscription travel newsletter Dream of Italy

By Walter Sanders

Montestigliano is a compound of historic villas and farm houses.

I felt at home in Villa Pipistrelli. That feeling of comfort was not an accident.

“It’s simple. We want our guests to feel like part of the family,” says Luisa Donati, marketing manager for the family’s Pipistrelli, Montestigliano, and Palazzo Donati Mercatello (in Le Marche) properties.

To feel like part of this family would be an honor. Signore Giancarlo Donati, the patriarch who’s in his 80s, is a talented business man with a big personality. Sixty some years ago, he learned to fly and bought a small plane. On one of his first flights he shocked the citizens of Mercatello by bombing the town with ripe peaches.

Virginia, the eldest child, is an architect, fearless singer, and animated dancer.

Massimo Donati discusses the olives that are raised to produce the family’s signature extra vergine olio d’oliva.

Massimo is the farmer who manages the olive oil production, as well as the family’s efforts in sustainable energy from BioGas methane transfer. He’s also the leader in solar energy capture on the properties.

Damiano is the family accountant, a spirited singer, and master griller.

Marta provides administrative support for the business.

Together, the family has integrated its dream of sustainability, tourism, and a unique Tuscan experience into a business model that revolves around Agriturismo. (An Agriturismo is a government designation for an operating farm that rents lodging and provides food from its own production.)

The Big Cena at the Montestigliano Property

Once a week, guests from the Pipistrelli and Montestigliano properties are invited to a dinner hosted by the Donati family in the spacious top floor of the old granary. The food is prepared by Anna, the talented young Polish chef, who has been with the family for nearly ten years.

All the food is procured from local suppliers. The olives for the extra virgin oil are grown on the property. Luisa introduced me to a cheese maker named Fiametta whose four different pecorino cheeses were featured. Luisa told Fiametta that she would have the opportunity to address the 60 guests and speak briefly about her cheese, and that Luisa would translate. Fiametta looked very nervous about the prospect but we both encouraged her to try.

By the end of the evening, after Fiametta had taken several orders for cheese purchases, she said to Luisa, “That was great fun, I want to do it again sometime soon!” Ah, a celebrity is born.

Luisa and Massimo make everyone feel like family around their dining table.

I mixed with some of the guests who were staying at the Montestigliano property. Many of them told me that they had been visiting for decades with friends and relatives (some multi-generational) in tow.

The meal was excellent. All five Donati siblings  mingled with the guests. After dessert Damiano grabbed the karaoke microphone and kicked off an hour of singing and dancing.

To be continued:

Palazzo Donati Mercatello and nearby attractions

This article first appeared in the October 2012 issue
 of the award-winning subscription travel newsletter Dream of Italy

By Walter Sanders

Flour and egg transformed into gossamer sheets of fresh pasta.

While staying at Villa Pipistrelli just south of Siena, our group visited nearby Stigliano. We were on a mission: to learn how make fresh pasta from scratch. Our teachers were two older women from the village. They were beautiful, gracious and patient. Pasta-making rookies began combining ingredients, and our enthusiasm was evident despite beaten eggs leaking from collapsed flour walls.

With the help of our lovely mentors, everyone finished their dough and formed it into a ball. All the balls were kneaded together, then rolled flat, cut, stuffed, trimmed and transformed into ravioli.

The site was La Bottega di Stigliano, a combination retail shop—specializing in locally produced agricultural products—and a restaurant. The building was a former casa del popolo, a people’s house where in olden times farm workers would meet to sell products. The casa also served as a social center. It was, in a sense, a one-stop shop where people could fill their baskets with food and make social connections. read more about making fresh pasta in Tuscany