All-Inclusive Italy: Under the ‘Middle-Aged’ Tuscan Sun

Italy Vacations, All-Inclusive Italy

All-Inclusive Italy

All-Inclusive Italy

Just as the sun was beginning to peek into my 18th-century room at a luxury hamlet in Tuscany, I begin to wake out of one of the deepest sleeps I had been in for a while. The glow of the sun tossed shadows on to the whitewashed walls and hardwood floors and I was curled up in my white comforter with deep hunter green and red flowers. My world had been turned upside down by all the changes going on in my new empty-nester life. Desperate to hang on to the past, yet searching still for the bigger meaning in my life. I had needed a break for a while, so I decided on this all inclusive Italy vacation.

I thought I heard the faintest sound coming from outside my window.

What was that?

All-Inclusive Italy

All-Inclusive Italy

Two of my sons moved away to college.

My boys were my anchors to the past and just like that… poof, they were gone in a flash. And I can’t blame them, I mean, who couldn’t wait to leave our parent’s house and get on with our lives? But I was a bit unsettled, in a funk. Many things in my life revolved around them, their school, and their world. Suddenly that whole chunk of my life was just GONE. These are supposed to be the best times of my life, right? The kids are gone! How is it that I can feel so empty? I was in that deep thought about who I am supposed to be when I heard that sound again.

All-Inclusive Italy

Sort of a “heeeee” sounds, then it faded away.

All-Inclusive Italy

All-Inclusive Italy

Then I remembered, I am not only at a luxury hamlet in Tuscany, Italy, but I am also on a working farm, an agriturismo. That is a very European word, that basically means that the government granted farmers the ability to turn their properties into places for people to stay as long as they were also a working farm. Well, this was the best looking working farm I have ever seen and perfect for all inclusive Italy!

All-Inclusive Italy


Villa Pipistrelli, Montestigliano, Tuscany, Italy, All-Inclusive Italy

Villa Pipistrelli, Montestigliano, Tuscany, Italy

All-Inclusive Italy

Quick Tuscan Farm History

There used to be farm workers who lived in this tiny town on the land that I am resting. But they worked for the landowner and in return, he built them housing and they shared in the profits of the farm. Basically, he would provide them a “tiny town” complete with a chapel where the priest would come once a week and they would work the land. Eventually though, after WWII, the industrialized world began to take over and the farm workers left the farm for better jobs in the city. Now the farmer was left with these “tiny towns” or hilltop estates, that would eventually become abandoned and go unused. That’s where my middle-aged Tuscan Sun story comes in!

Enter Montestigilano and its History

All-Inclusive Italy

All-Inclusive Italy

My friends, the Donati family, decided to turn their “tiny town” into a luxury hamlet that they had acquired in the 1950’s. In fact, they received the very first permit ever granted in Tuscany for an agriturismo! They turned their hilltop estate into the luxurious Montestigilano. But this agriturismo is unlike any you have ever seen. It is like your deepest fantasy of luxury Tuscany Italy coming to life. It is the epitome of being under the Tuscan sun. It is the place where you will want to go and never leave. This is the perfect all-inclusive Italy.

It is the perfect place for me in this middle age of my life.

Montestigliano, Tuscany, Italy, All-Inclusive Italy

Montestigliano, Tuscany, Italy

All-Inclusive Italy

I was fascinated upon my arrival the first time I had been here and this time I knew I needed it more than ever. A place where I could go and actually sleep and dream. A place that is truly in your imagination, but quickly becomes a reality once you have arrived. A place that makes you wonder about the way you do things and the way you live your life. A place with long family tables and a chef that is a member of the family.

All-Inclusive Italy

Where his delights are to showcase and serve you his handmade Italian specialties. Where real people come for dinner outside and make conversation without their cell phones. Where you can take long walks in the woods with a stream nearby, where you can wake up early or late with magnificent and iconic Tuscan views.

All-Inclusive Italy

All-Inclusive Italy

Where you can go for a dip in the pool or have an olive oil tasting demonstration. Where wine is flowing and so is the friendships you will make.

All-Inclusive Italy

All-Inclusive Italy

This time on my visit, instead of staying in the hamlet up at the top of the hill, Villa Pipistrelli, I decided to stay down amongst the other apartments within the private town, at Casa Luisa. Other options included the two-story Villa Donati that sleeps 14 (but that was too large for me on this trip to Italy) with its private garden, or the smaller Casa Massimo near the chapel, or the Casa Emilio, a stand-alone apartment. Casa Luisa, the 5 bedrooms, 2 bath hamlet with a full kitchen and living area was perfect as I was going to be with a group of middle-aged travel writers and we needed our space. That’s the deal here at Montestigliano, the choices are endless on what you need for the perfect Tuscany vacation. The choices are seamless depending on what you need and where you are at in the timing of your life. And all the luxury apartments have easy access to the olive groves, the views of the Siena towers, and the iconic cypress trees jutting out of the landscape. Every apartment has easy access to some of the most beautiful countryside in all of Tuscany. But that is not ALL they have.

All-Inclusive Italy

That is only the view!

Montestigliano, Tuscany, Italy, All-Inclusive Italy

Villa Pipistrelli, Montestigliano, Tuscany, Italy

All-Inclusive Italy – The true luxury of this place…

is the serenity, peace, and the food-coma-induced family gatherings. Those are things that I remember the most about Montestigliano. The stillness of the misty mornings, the sounds of the land waking up in the morning. And the family gatherings with the most amazing food that your belly has ever had to digest. Here the people gather, they laugh and talk, deep into the night around copious amounts of food and wine. Here in Tuscany, they know how to truly live at this all-inclusive Italy resort.

All-Inclusive Italy

All-Inclusive Italy

Oh, and by the way, that sound I heard was the sound of a donkey braying!

All-Inclusive Italy

You may recall the last time I was here, I felt as though it was like a religious experience, A Journey for the Soul! This time, I knew a few days in Italy could help me with the anxiety of my changing life.

Montestigliano, Tuscany, Italy, All-Inclusive Italy

Montestigliano, Tuscany, Italy

If you want to feel like you are “Under the Tuscan Sun”, I have found that place where you can feel like Diane Lane without actually moving in… Montestigliano – a quiet gem of a luxury farmhouse in Tuscany.

All-Inclusive Italy

You may have heard that “Orange is the new Black?”

 Well, in Italy,

 “Luxury Farmhouse Stays are the New Luxury Hotels in all inclusive Italy.”

All-Inclusive Italy

Recommended Reading Before You Go

To find out what there is to do there, read my article on Huffington Post:

The Masterpiece that is Montestigliano

or my

Flipboard Magazine  entitled: The Masterpiece that is Montestigliano

Authentic Italian Recipes for the Soul

For other reading about Italy by Region:

*LeMarche Region, Italy:

Make this Your Next Authentic Italian Vacation

Food, Friendship, and Wine in Le Marche Region, Italy

The Lost Art of Print Blocking in Carpegna, Italy Regenerated

*The property mentioned above in all three articles, Palazzo Donati, is also own by the Donati Family and is a separate, but just as authentic journey deep into Italy.

Donati Family, Montestigliano, Tuscany, Italy, All-Inclusive Italy

Donati Family, Montestigliano, Tuscany, Italy

Disclosure:  The writer believes in full disclosure and wanted to let you know that this trip was provided by Montestigliano.  As is common in the travel industry, the writer was provided with accommodations, meals, and other compensation. 

All-Inclusive Italy

All-Inclusive Italy


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  1. Jenn August 3, 2017 at 7:47 am

    What a beautiful place to visit. You photos are stunning. I bet it was even nicer in person than it looks in your photos.I would love to travel to Tuscany one day. As much I enjoy traveling, our budget doesn’t let us very often. maybe someday though.

    • Cacinda Maloney August 3, 2017 at 7:51 am

      Thanks, and yes, this place is stunning!

  2. Vicky August 3, 2017 at 9:58 am

    I feel like I went on a getaway just reading this post! Wow, I would love to go there some day and it seems like the perfect place to deal with an empty nest. The food must have been amazing and the scenery and nature. You are a lucky lady!

  3. Lisa Favre August 3, 2017 at 10:33 am

    What a wonderful set up you have right now. Architecture and history aside, the food that you have photographed looks fresh and incredible! Enjoy yourself and looking forward to more articles on this!

    • Cacinda Maloney August 8, 2017 at 11:47 am

      Ahhh, thanks, yes many more stories to tell!

  4. Melanie August 3, 2017 at 8:38 pm

    Your photos make this place look so amazing. I would like to visit one day. I have four kids at home, and I can only imagine how much empty nest syndrome that I will have when they are graduated and gone.

    • Cacinda Maloney August 8, 2017 at 11:46 am

      I know, right? They grow up so fast! Thanks for the comment on my photos, it is a joy of my life!

  5. Kimberly @ Berly's Kitchen August 4, 2017 at 5:34 am

    Oh, my! I am absolutely in love with your photos and this area. It looks so quaint and peaceful. Sounds like you had a wonderful time. What a lovely place to vacation. I could easily stay there permanently if given the option! Lol!

  6. NYC Single Mom August 4, 2017 at 6:07 am

    I love the idea of staying at “farm” The last time I went to Italy we rented a house in Tuscany but used it as a base to travel the region and had to cook for ourselves. This sounds like such an amazing option. Will be bookmarking this post for later!

  7. liz Cleland August 4, 2017 at 1:24 pm

    Now, this is a place I would love to visit. The wonderful structures of that deep almost red clay. Wonderfully photographed!

  8. adriana August 4, 2017 at 9:09 pm

    Isn’t Italy just amazing?! I love Tuscany too – it’s gorgeous! My family is from Italy so I go there a lot, but stay in the south a lot. I love taking trips to the north! So gorgeous and your pictures are so amazing!

  9. Bites for Foodies August 5, 2017 at 4:18 am

    Such a beautiful place! I’m living in Sardinia right now….we usually come every summer but have decided to stick around for a few years. If you ever got out this way you have to go to my compare’s agriturismo, Tenuta Pilastru! It’s stunning and the food is amazing!

    • Cacinda Maloney August 8, 2017 at 11:43 am

      Yes, I will have to try it out!

    • Cacinda Maloney August 8, 2017 at 11:44 am

      Thank you! and yes, I love Italy, too!

  10. Ali Rost August 5, 2017 at 6:37 pm

    I remember the season of life when I too became an empty nester. How surprised I was that it felt so strange. For a while I was sad, but then decided it was such a great opportunity to reinvent my life. Good for you for going to a place that was peaceful and made your soul happy. I can’t believe how beautiful it is. My grandparents were missionaries and lived all over the world. The place my grandmother loved most? Italy. xxxoo

    • Cacinda Maloney August 8, 2017 at 11:42 am

      Yes, I am sure it is just a season and will pass! Isn’t this a wonderful place to stay?

  11. Burcin Kolak August 16, 2017 at 1:31 am

    What a wonderful telling of the place.. Your sentences take me there I feel I were there. Stillness of the misty mornings and sounds of the land waking up in the morning in Montestigliano. Thanks for sharing.THis is amazing post and pictures are perfect.

    • Cacinda Maloney August 16, 2017 at 10:11 am

      Thanks! As you can tell, I love Montestigliano.

  12. Agness of Fit Travelling August 23, 2017 at 6:08 am

    I loved your pictures, Cacinda! When’s the best time of the year to visit Tuscany?

    • Cacinda Maloney August 23, 2017 at 11:10 pm

      Ahhh, thanks! April, May, June, September, and October is best, peak season and pleasant weather.

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