Northern Italy Dream: A Stay at a Luxury Farmhouse in Tuscany

Because there are so many incredible places in the world to see, there are only a select few destinations that I ever return to on my travels. Northern Italy is one of those locations that I could never turn down. I never say no to pasta!

After my first holiday stay at Montestigliano luxury farmhouse in Tuscany, there was no question when the opportunity came around for a second visit that the answer would undoubtedly be “yes”. Its burnt orange 18th-century buildings, million dollar landscape view and peaceful lifestyle makes it the perfect place to getaway to again and again.

It is a Tuscan dream.

About Montestigliano

Montestigliano is a sprawling 2500 acre estate where people come on holiday to be immersed in the Italian countryside. Whether it be sitting on the terraces to take in the view of the July sunflowers or hiking through the cypress lined trails, it is truly a place to unwind.

It is particularly memorable in the summer months where the warm nights bring opportunities for dining alfresco in the large community courtyard or simply sipping on a glass of Chianti in the garden patio.

The estate is a family-run agritourism, a working farm that brings visitors to stay on holiday. The Donati family acquired it in 1959 after researching over 80 properties before deciding on this one.

So you know it must be special.

The farmland that surrounds the luxury villas features a large olive grove, that produces some of the most delicious Tuscan olive oil, along with a vegetable garden and meditation garden — Il Giardino Sei Sensi.

It is the epitome of a family run business, everyone is involved in some way.

From Luisa, the sweet marketing director, to her older brother Massimo who tends to the land and is affectionately called “the farmer”. There is also Damiano whose title as the head of hospitality is fitting after you hear him belt out a rendition of “That’s Amore” during a meal at the estate. Plus Francesco, who is in charge of guest relations, is always around the property offering a charming smile.

You can see and feel their love for this property.

The Hamlet

The hamlet is an area with 11 renovated villas that give you luxury while still keeping their old world charm. There is also a central piazza that holds many lively meals, complete with all the Tuscan food you could possible dream of (my favorite was the creamy pesto gnocchette!). It is a section of the estate where guests can be as secluded or social as they want.

On this particular visit, my lodging was in Casa Luisa, a traditional farmhouse that boasted views of the Chianti hills. Each morning, opening my windows led to the sweet sound of birds chirping and a walk through the yard led to crawling rose vines to my left and olive trees to my right.

Can I just live here?

The Montestigiano hamlet includes every farmhouse, except for Villa Pippistrelli…

Villa Pippistrelli

As if this Tuscan dream wasn’t good enough, further up a gravel road, through the fog encrusted trees that lined it, you will find the extraordinary Villa Pippistrelli. Walking distance from the hamlet, this splendid villa is tucked back in the woodlands with views of the Siena hills.

It is the sort of place that fairytales are made of.

The elegant rooms of the villa can sleep up to 14 people comfortably, perfect for a bridal party or an exquisite family holiday. With its own infinity edge pool, secluded garden and surrounded by layers of trees, Pippistrelli is meant for privacy.

On my first visit to the estate I was lucky enough to stay here. Read about it: Stay in a Tuscan Villa

What to Do

At Montestigliano you can be as relaxed or active as you like. Believe me, you’ll be surprised by how many hours can easily be spent just sitting in a Bougainvillea covered courtyard reading a good book with a glass of Italian wine.

On any given day you may just choose to lounge on one of the many chairs scattered throughout the estate or go for a refreshing swim, but you may also choose to take advantage of the optional activities that the estate and nearby towns have to offer.


The Montestigliano property has over 2,000 olive trees, which produces about 2,000 liters of delicious olive oil each season. The olives at the estate are handpicked and then brought to the grainery to be turned into an Italian treasure.

In this grainery is where you can do a blind olive oil tasting. Massimo (the farmer) will explain how to cultivate and properly taste an olive oil, then lead you in a sampling to see if you can pick out the best.

Read More: A Blind Olive Oil Tasting


The estate is surrounded by with nature and there are plenty of opportunities to enjoy it. It could be a simple 45-minute hike through the 2000 year old cypress trees to the town of Brenna for a cappuccino or a longer walk along the river channels  to one of the three castles: Castiglion Che Dio Sol Sa, Spannochia and Montarrenti.

You can choose to stroll alone or let Caterina, a local guide, escort you while explaining the local history and foliage along the way.


Set up a wine tasting at the estate where you can learn about the local growing regions and taste a selection of Italian varietals. We tasted a number of different Chiantis from the nearby region. This is a special treat because it was done on a perched terrace overlooking the hills of Tuscany. It doesn’t get much better than that!


Another beauty to Montestigliano is that it is located near many cute towns. Within an hour you can have hundreds of different Tuscan experiences! The main city that draws visitors to the area is Siena, and it’s only about 20 minutes away.

Siena (distance: 12 miles, approx. 20 minutes)

Siena is a city in Tuscany thats historic center is recognized as an UNESCO World Heritage site. It’s best know known for its medieval architecture, yearly Palio horse race and cobbled roads lined with quaint shops. It’s close proximity to the estate, makes Montestigliano the perfect destination for a balance between big city life and relaxing farmhouse.

There are so many other cute towns close by too, here’s a few:

Volterra (Distance: 32 miles, approx. 1 hour)
San Gimignano (Distance: 30 miles, approx. 1 hour)
Montepulciano (Distance: 45 miles, just over an hour)
Chianti (Distance: 37 miles, just over an hour)


While staying at Montestigliano it is an option to participate in some specially cooked meals where the guests either dine alfresco in the piazza or, in the colder months, inside a large stone hall.

These meals are lively and so much fun, not to mention filled with absolutely delicious food. If one of the options at your time of stay is “Pizza Night”, BOOK IT. It was my favorite (because who doesn’t love pizza!?!). Wine will be flowing and the chef will bring a seemingly endless stream of fresh pizza cooked in the wood burning oven. To top it all off, the dessert was nutella and orange pizza.

The Montestigiano estate is perfect for everyone. It is great for groups who want to organize a retreat, for a stunning destination wedding or simply for couples who want the romance of Tuscany to spill over into their lodging.


Website/Booking: Montestigliano Farmhouse Holidays in Tuscany

Location: Loc. Montestigliano Fraz. Brenna 53018 Sovicille (SI) Italy

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12 thoughts on “Northern Italy Dream: A Stay at a Luxury Farmhouse in Tuscany”

  1. I loved these photographs really they are very awesome and staying in these types of farmhouse gives the best feeling of life thanks for sharing this post.

  2. Food is looking delicious and place is looking amazing. Thanks for sharing such a great article. It’s luxurious.

  3. Italy is so gorgeous, and that view is amazing! I love how they have the long family style table. After watching Under the Tuscan Sun, I’ve wanted to go back to Italy to see Tuscany, and you’ve captured exactly what I imagine Tuscany to be!

  4. Annette, you’re a woman after my own heart! You captured Northern Italy so beautifully and thanks for showcasing the quieter gems in Tuscany – too often it’s Florence, Florence, Florence. Farm stays are definitely where the action is – so happy you got to experience that. If you’re in Puglia or Piemonte we can recommend two we stayed in – still friends with the owners today! Like Robbie said in her comment – the first time I stayed in one I felt like Diane Lane in Under the Tuscan Sun (without actually moving in!). Congrats on your stay and thank you for sharing so deeply about your trip!

  5. We’ve been tossing up weather to do an agriturismo stay in Italy and this is definitely swaying us to book. Looks delightful. Thanks for sharing


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Annette White the Owner of Bucket List Journey
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