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.
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.
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.
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.
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.
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.
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.
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.
Related
Florence Bucket List: 40 of the Best Things to Do in Italy’s Top City
Northern Italy Dream: A Stay at a Luxury Farmhouse in Tuscany
10 Foods for your Italy Bucket List
Stay in a Tuscan Villa in Italy
Drink a Bellini at Harrys Bar in Venice, Italy
11 Things Restaurants in Italy Do Differently
Scale the 463 Stairs of the Florence Duomo
Italian Adapters, Converters & Voltage (AKA: The Flat Iron Dilemma)
10-Day Northern Italy Itinerary
It looks like a Hollywood movie fantasy come to life! I could happily spend a week there.