Stay in a Tuscan Villa in 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 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.

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.

Tuscan Villa in Italy
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.

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.


Florence Bucket List: 40 of the Best Things to Do in Italy’s Top City
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Stay in a Tuscan Villa in Italy
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24 thoughts on “Stay in a Tuscan Villa in Italy”

  1. This place looks awesome, I like the nature surrounding it and the rustic look the villa has. I wouldn’t mind spending some time there too :)

  2. When I saw your post I called my husband right away and told him we need to go. Well we have decided, although a little far into the future, that we will book a villa in Spring of 2017. We will be taking our three boys as well. Thank you for sharing your expereince.

  3. That Italian style breakfast is something I would very much enjoy eating every day for the rest of my life. I can’t believe how amazing everything looks. The whole experience seems really chill and relaxing.

  4. The whole place looks so beautiful. I loved Tuscany when I went there, but I never stayed anywhere as lovely as this place. It makes me want to go back there again. :)

  5. This place looks so beautiful and charming! I can see why you were sad to leave – it looks like the sort of place I would want to stay for at least a month!

  6. Wow, it isn’t discount prices for a discount traveler here but I’m sure it’s an awesome experience. Let alone, living in a country side in Italy. Mama mia! :)

  7. Where did you find that villa! I usually search Reservation Counter for places to stay but I have never seen such a beautiful place before. Yeah… but as I found the price is super steep! 7400 EUR in a low season? Can you recommend something cheaper in the range of 2000 EUR?

    • They have several other options on the Montestigliano estate starting at 700 euros per week. Villa Pipistrelli just happens to be the most luxurious, but it also large and sleeps up to 10 people, so this makes it ideal for two or three families to share.

  8. Annette, A stunning description of a spectacular property! I was part of a journalists group in the fall of 2012 and was so captivated by Villa Pipistrelli and the wonderful Donati family that we created a series of tour adventures to bring guests to the Villa. I’m not sure what your policy is about sharing travel opportunities…but our two Tuscan Harvest Adventures in October are still available. More details at

    Your photography captures the special mood of Villa Pipistrelli, and I agree that it’s a perfect destination for a family group, special friends, or a unique event for an intimate group. Thanks again for a wonderful article.

  9. Sounds like a great location to stay and write. Thanks for providing somewhere for me to dream about. The countryside sounds, from your descriptions, to be incredibly peaceful.


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Annette White the Owner of Bucket List Journey
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