Montestigliano – Olive Oil DOP

We are proud to announce that our Olive Oil has won an award. Massimo and Luisa Donati attended the awards ceromony yesterday.

One of four Olve Oils chosen as the best in the ‘Terre di Siena’ – D.O.P



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Simple Italy: Italian Food, Culture, Lifestyle and Travel


Simple Italy: Italian Food, Culture, Lifestyle and Travel

Tuscany Tour: Harvest Celebration with SimpleItaly

Vendemmia-the grape harvest in Tuscany is the culmination of a year's labor and love.

La vendemmia–the grape harvest in Tuscany–is the culmination of a year’s labor and love.

Two departures: October 11-18, 2014; October 18-25, 2014

In autumn, la vendemmia (the wine grape harvest) envelops the countryside of Southern Tuscany. Wine production has defined the region’s culture and economy since antiquity. The sense of achievement at the culmination of a year’s effort is palpable. Celebration ensues as each community hosts a sagra (harvest festival).

Grilled Tuscan porchetta is seasoned with rosemary, sage, garlic, and olive oil.

Grilled Tuscan porchetta is seasoned with rosemary, sage, garlic, and extra-virgin olive oil.

In the Chianti Classico Zone, the Colli Senesi, Montepulciano, and dozens of other districts, workers snip ripe fruit clusters from the vines. The aroma of sweet, spicy crushed grapes perfumes the air. Wild foods flourish: blackberries, juniper berries, chestnuts, and hazelnuts. Porcini mushrooms burst to life in patches where the sun penetrates the dense leaf carpet under firs, chestnuts, oaks, and pines. The fungaioli (mushroom hunters) scour their secret spots plucking the coveted funghi that fetch such a handsome market price.

Sangiovese grape vines proliferate throughout central Tuscany.

Sangiovese grape vines proliferate throughout central Tuscany.

Tuscany is the most forested of any Italian region. Acorns abound for the cinghiale, those fearsome wild boars that are prized by hunters. Tuscans love their game. This time of year, ragù of duck, rabbit, partridge, or wild boar is ubiquitous, tossed with wide strands of tender pappardelle. Fig and walnut trees nestle around the ancient stone farmhouses, while cypresses stand sentinel on the hilltops. In an ideal year, cool mornings and evenings give way to sunny mild days even into November. Gold and crimson leaves complement the ochre walls and terra cotta roofs of the stone dwellings. Indoors, cooks tend huge crackling hearths to roast herbed porchetta to savor with vino rosso.

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In your Tuscany Tour: A Harvest Celebration, you’ll unpack only once. Your small group (limit 12) will share the seclusion and luxury of Villa Pipistrelli. You’ll partake of off-site adventures, on-site experiences, and the gift 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 watching it flash by from the windows of a motor coach. You’ll arise and venture to la terrazza serena to witness the dawn paint thousands of acres of pristine woods in morning splendor. Or, at sunset, raising a glass of vino rosso, you can whisper buona notte to the fading light.

Luisa, Damiano, and all the Donatis welcome their guests like family.

Siblings Luisa and Damiano Donati welcome their guests like family.

You’ll go as hard or easy as you choose over walking trails along cypress-lined lanes or through forest stands of old oaks. You’ll release your Inner Italian artist with a watercolor painting lesson. You’ll dance to a refreshing new rhythm—a well-deserved escape from the hectic day-to-day. You’ll benefit from the wisdom of experts sharing their insider perspectives with access to an exclusive visit to a wine estate with lunch, private tour of a Palio contrada in Siena, and a tour and luncheon at a wine estate near Montepulciano.

Early morning mist rises from the hills in Southern Tuscany.

Cool autumn mornings create the dream-like mists that rise from the hills in Southern Tuscany.

On the Art & Culture Day and Artisanal Food & Wine Day, the presenters will come to you so you can spend time learning from, and interacting with, these talented folks. You’ll savor la cucina, la cultura, l’arte, i giardini, i vini, and la vita bella that Tuscans are so blessed to call their own. You’ll create memories to last a lifetime during your Tuscany Tour: A Harvest Celebration.

W S Montestigliano ViewWalter and Sharon met in Florence, fell in love, and married there in the Basilica di Santa Croce. Walter studied art history at Northwestern University then worked at The Leather School and Sharon was traveling with St. Francis University. Living and working In Tuscany transformed their lives. They ran their first intimate tour to Italy in 1978. They love sharing their perspectives and experiences  with others interested in Tuscany.

Read What Folks are Saying about SimpleItaly Travel Experiences!

For a Summary of the Fall Itinerary, click here!

Fall Tour Online Registration and Electronic Payment Form

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  • Rob Cook
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  • flower market

Tuscany Tour: Harvest Celebration Daily Itinerary

Villa PipistrelliDay 1–Saturday
Your program begins Saturday afternoon on the secluded hilltop estate of Montestigliano. Curated by siblings Luisa, Massimo, Damiano, Virginia, Marta, and their concierge, Francesco, you’ll be treated like part of the family. Explore the stunning private grounds overlooking pristine wooded hills and valleys.

Evening welcome antipasti and vini to get acquainted and discuss the upcoming adventures.

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Day 2–Sunday

Local Sagra

Toasting the grape pressing.

Saluting the season at Montestigliano.

La Colazione (breakfast) at Villa Pipistrelli is abundant: typical offerings may include brioche, cheese, bread, prosciutto, yogurt, pancakes, fruit, jam, honey, coffee, and tea. Afternoon at a sagra, a harvest festival where we join the locals in celebrating the bounty of the season’s harvest. For lunch, you’ll snack on festival fare. La cena (dinner) with wine at Villa Pipistrelli: Hand-made pastas, seasonal vegetables, porchetta, grilled meats, salads, and local pecorino cheeses are among the offerings.

Day 3-Monday

Artisanal Food and Wine Day

Massimo prepares for the olive oil tasting.

Massimo prepares for the olive oil tasting.

This casual learning session brings local artisans and guest experts to your Tuscan villa. La colazione at Villa Pipistrelli. Comparison extra-virgin olive oil tasting with Massimo Donati, manager of the farm at Montestigliano. Pecorino Senese cheese-making demonstration with tasting. Local producers with samples of Colli Senesi wines. Tasting of porcini, castagne (chestnuts), salume from heritage hog breed cinta Senese, and other autumn specialties with opportunity to purchase foodstuffs. Participation pasta-making class. You’ll mix, knead egg-flour pasta dough and then roll it out by hand-cranked machine. You’ll master the secrets of preparing silken pasta sfoglia.

Artisanal salume are the pride of the Tuscan table.

Artisanal salume are the pride of the Tuscan table.

Il pranzo (lunch) with wine and the guest artisans and producers. Free time gives you the opportunity to explore the walking trails, the farm at Montestigliano, capture photo images, write, sketch, or relax in the game room at the renovated Granary. Dinner with wine at Villa Pipistrelli.

Day 4-Tuesday

Montepulciano's Church of San Biago.

Montepulciano’s Sanctuary of San Biago sits outside the city walls aside the road to Chianciano.

La colazione at Villa Pipistrelli. You’ll journey south to a 1,900-foot-high limestone ridge has been home to Etruscans, Romans, Lombards, Sienese, Florentines, and now you. You’ll be welcomed at the Poliziano Winery by host Jen Criswell, certified sommelier and author of At Least You’re in Tuscany. Light lunch and tasting of the area’s signature wine Vino Nobile di Montepulciano made from Prugnolo Gentile (Sangiovese). You’ll also sample the reserve bottling Vino Nobile di Montepulciano Selezione Asinone DOCG which is only made it harvest fine enough to warrant the designation. The 14th century city walls encase the steep stone streets. Many fine Renaissance palazzi line the Via Ricci and Via Roma. You’ll step into the bel’epoca era at Caffè Poliziano. At Bottega del Rame workshop and museum, you’ll see the hand-crafted objects of third-generation coppersmith Cesare Mazzetti. La cena with wine at Villa Pipistrelli.

Day 5-Wednesday

Construction of the Duomo began in X

The Duomo of Siena dominates this medieval city. Construction began in 1215.

La colazione at Villa Pipistrelli.

Dario Castagno

Dario Castagno, author Too Much Tuscan Sun: Confessions of a Chianti Tour Guide will share a behind-the-scenes tour of the Bruco (Caterpillar) Contrada museum during the Oct. 18-25 program.

Today, you’ll immerse yourself in the rich history, culture, and art of Siena. The walled medieval city is a UNESCO World Heritage site. First, the Piazza del Campo, considered by many to be the most beautiful piazza in Europe. Shaped like a scallop shell, it is sited on the spot where the three city hills converge. It is here that the historic Palio bareback horse race takes place each July 2 and August 16. There is fierce rivalry among 17 contrade (neighborhood clubs). You’ll tour a contrada museum to learn about the intricate role the contrade play in Sienese life 365 days a year. You’ll visit the church and the museum of Siena’s cathedral, one of the finest examples of Italian Gothic architecture. It dazzles with its signature greenish black-and-white horizontally striped campanile (bell tower) and interior marble pillars. Free time to stroll the winding streets that have remained unchanged for centuries. Many alta moda boutiques , particularly on Via Bianchi Sopra, and artisan shops beckon. This is also an opportunity to purchase Tuscan wines at one of Siena’s enoteche (wine shops). La cena with wine at Villa Pipistrelli.

Day 6-Thursday
Art and Culture Day

La colazione at Villa Pipistrelli.

Art Class Art Therapy Class: a local artist leads you in creating your own watercolor paintings. This two-hour session allows you to unleash your Inner Italian Artist and give you a unique souvenir of your stay in Tuscany.

Guest experts will speak about Italian travel and culture. Learn what it’s like to actually reside in Italy, not just visit as a traveler. Il pranzo with wine. Mingle with special guests. Free time gives you the opportunity to play golf, visit the spa, explore the walking trails, the farm at Montestigliano, capture photo images, write, sketch, or play in the game room at the Granary. La cena with wine at Villa Pipistrelli.

Day 7-Friday

Vino rosso is the lifeblood of Tuscany.

Vino rosso is the lifeblood of Tuscany.

Friday on the Estate

La colazione at Villa Pipistrelli TGIF. . .Tuscany’s Great In Fall. . . revel in the immersion experience of life on a country estate that dates from the 1700s. Learn about the loving and painstaking process by which the Donatis are converting ancient farm buildings into inviting holiday homes.

The piazzaolo creates hand-crafted pizzas in the wood burning oven at Montestigliano.

The piazzaolo creates hand-crafted pizzas in the wood burning oven at Montestigliano.

Consult with the pizzaiolo to top your own pie at the farewell pizza party at Montestigliano. Damiano will DJ some tunes that will get you out of your seat to dance.

Day 8-Saturday

Morning departure Continental breakfast Villa Pipistrelli Independent departures by 10 a.m. To book the tour: Tour Price: US $2,995 (per person double occupancy, ground only) Deposit: US $750 Final Payment: US $2,245 (due by July 1, 2014) To make a booking, read the Terms, Costs, and Conditions (downloadable). Use this secure link to complete the Registration Form by email (or snail mail). Payment may be made online with credit card or debit card  to PergolaWest, Inc.’s PayPal account or with personal check or money order. Summary Itinerary Questions? contact us here.

The courtyard at Montestigliano welcomes you.

The courtyard at Montestigliano will be your private piazza.

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A big thank you to the DeConno family for sharing this wonderful video of their time at Montestigliano. Staying at Villa Pipistrelli , they relaxed , enjoyed the estate and visited many places of interest including Siena at Palio time!
We hope to see you back at Montestigliano in the not too distant future.
Cari Saluti!

A week at Villa Pipistrelli by the DeConno family


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Stay in a Tuscan Villa in Italy – Bucket List Journey

The Montestigliano Estate near Siena – Tuscany.

Stay in a Tuscan Villa in Italy

Stay in a Tuscan Villa in Italy

Written by Annette White

Topics: BY DESTINATION., Europe, Italy

There has been a not so secret fantasy that has occupied my mind over the last few years. It is the one where I leave all the stresses of life behind to escape to the hills of Northern Italy and live in a charming, old Tuscan Villa. A classic dream that blends a little Eat, Pray, Love with a bit of Under the Tuscan Sun.

A version of this fairytale became a reality at Villa Pippistrelli. At least for four perfect nights.
Tuscan Villa in Siena, Tuscany, Italy

After arriving in Florence, we drove just a few kilometers South of Siena to Villa Pippistrelli, a luxury Tuscan farmhouse located on the Monstegliano estate. Driving down a lengthy gravel road, and through the fog encrusted trees that lined it, appeared the prettiest villa I had ever seen. 

This was so much better than watching a rerun of Under the Tuscan Sun on television.

The front of the villa was a terra cotta colored brick and the land surrounding it a dozen shades of green. Inside the arched entrance, a long outdoor table in the front courtyard was begging for diners and several bottles of Chianti.

I would happily volunteer to occupy a seat there.
Tuscan Villa in Italy

Walking inside of the front door, a small country kitchen sat to the right and the sitting room with a blazing wood burning fire to the left. Straight ahead was a dining room where we would share many meals together.

I chose a twin bedroom downstairs adorned with floral comforters and all the modern amenities: on-suite, powerful shower, a heater and a sitting area. Plus, when the shutters on the windows were open, the rolling hills peeked in.

Every other room on site was just as charming and quaint, I could not have made a bad choice.
Bedroom at Villa Pipistrelli Tuscan Villa
Bedroom at Villa Pipistrelli in Tuscany

It may be old in years, but the villa has been restored with present-day conveniences and elegant interiors while still keeping its rustic 17th century Tuscan feel.

This dream was turning into an incredible reality.

Each morning a talented chef prepared an Italian style breakfast that was filled with meats, cheeses, crostata, fruit and even Nutella crepes on one very special morning. A nourishing beginning for what the days adventures may bring.
Tuscan Kitchen at Bedroom at Villa Pipistrelli in Italy
Frittata Breakfast at a Bedroom at Villa Pipistrelli Tuscan Villa in Italy

The Montestigliano estate has several villas on premise, Pipistrelli being the most luxurious and set away from the others. Each morning, after overloading on crostata and cheese, I strolled around the lush grounds inspecting nearly every inch.

The estate is spread over 2475 acres, so there is plenty of room to roam.
Villa Pipistrelli in Tuscany
Frog on a Lily Pad in Tuscany

When you want to be more social, take the walk down to the center of the Montestigliano hamlet to meet the guests staying at the other properties. Or go worship at the tiny chapel.

In the middle of this tiny village is where I did a blind olive oil tasting with Massimo, celebrated an Easter dinner with 70 other guests and had a delicious wood-fired pizza night.

This center is the heart of Montestigliano.
Tuscan Villa Courtyard in Italy
Flowers at a Tuscan Villa in Italy

When you are looking for some peaceful exercise, Montestigliano offers hours of picturesque hiking trails on the estate. But, the one that was the most rewarding (and the trail that I hiked) is the trek that will bring you to a hot cappuccino reward.

It was a moderate hike that took about an hour and led to Vecchio Tinaio café in the Tuscan town of Brenna.
Annette White Hiking in Tuscany, Italy
Italian Cafe

There were only two customers when we arrived, two older men who seemed like regulars. One of them, Juliano, spent a half  hour chatting with us in broken English and a version of Italian charades about marriage, children and his wife that had gone to heaven, as we gathered from him pointing to the sky.

I have hiked to many things: a waterfall, a lake, a vista peak. But, this one from a Tuscan villa to a cappuccino in an small Italian town may have been the most rewarding.

The last day on the estate was bittersweet as I knew we must move on to explore other areas of Northern Italy. But, a little piece of my heart was left at Villa Pipistrelli, because it is a place that dreams are made of.

DETAILS: Villa Pipistrelli is a luxury Tuscan villa that is part of the Montestigliano estate and located about 15 minutes Southwest of Siena. Not only can you do the activities mentioned above, but many other adventures can be arranged while staying at any of the beautiful Montestigliano Tuscan villas.

Prices vary depending on the season and size of villa, but the range starts from 700 Euros per week.  Montestigliano Pricing. Villa Pipistrelli Pricing.

Address: Montestigliano Fraz. Brenna 53018 Sovicille (SI) Italy | Map
Website: Montestigliano Estate and Villa Pipistrelli | Contact:

Disclosure: I was a guest of Montestigliano, but all the words I write come straight from my, sometimes distorted, mind. Just as it should be.

Stay in a Tuscan Villa in Italy – Bucket List Journey

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