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.

OLIVE OIL TASTING
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

HIKING
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.

WINE TASTING
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!
TAKE A DAY TRIP
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)
DINE AT THE ESTATE
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.
Details
Website/Booking: Montestigliano Farmhouse Holidays in Tuscany
Location: Loc. Montestigliano Fraz. Brenna 53018 Sovicille (SI) Italy
Traveling Soon? Use my Favorite Resources for Booking Your Trip!
Book Your Flight
Skyscanner is my favorite flight search engine, because it checks dozens of airlines so you can easily find the best fare deals. You can also select ‘cheapest month’ to find the lowest fares for your destination (I use this all the time!).
Book Your Accommodations
I use both Booking.com and Expedia for hotels, because each offers a couple different hotel choices and I like to compare the reviews on each one. If you have a group or are looking for more of a home atmosphere, head over to VRBO or AirBNB that has houses, apartments and even just a room for rent in every price range.
Book Your Rental Car
If love the freedom to explore like I do, driving from place to place is the best option! I always book with Discover Cars for the best prices and top brand options.
Book Some Fun Tours!
Viator and Get Your Guide are my go-to search engines for cool bucket list experiences! Each one can have different tours, so check both—why limit yourself, right?
Don’t Forget Travel Insurance
Travel can be unpredictable. Whether it’s a last-minute cancellation, an injury, or (ugh) theft, things happen. That’s why I recommend never leaving the country without travel insurance. Here are my faves: Safety Wing and World Nomads.
Get Packing & Travel Essentials Ready
Check out the Bucket List Journey Amazon Store to find all my favorite travel essentials. Everything from Packing cubes, to travel adapters and toiletry containers to walking shoes.
*Lastly, check travel.state.gov for visa requirements and safety information.
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Beautiful scenery, impressive wall designs. It’s enjoyable to admire the lovely Tuscan views.
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
Tuscany is just as beautiful as I imagined. I can’t wait to see it next year! <3