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

About Montestigliano Farm Holidays in Tuscany

The agricultural estate of Montestigliano is centrally located in the heart of Tuscany. Perched high on a hill, at a height of approximately 300 metres, the estate commands magnificent views of the Sienese landscape. It has been owned by the Donati family for over 50 years and is still today a working farm.
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