Italian Vacation in Southern Tuscany

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A Spectacular Vacation in Valdorcia

For an Italian vacation in southern Tuscany, there is a stunning area called Val d’Orcia, also known as Valdorcia, an enchanting valley near the Orcia river plane and one of the most beautiful locations in the Province of Siena.

Italian Vacation in Valdorcia Tuscany
Romantic Farmhouse in Beautiful Tuscany

It’s no wonder Val d’Orcia is also a Unesco World Heritage Site. The landscape is picture perfect and every turn in the winding roads offers spectacular views.


For a romantic Italian vacation, plan early to select a room or suite at one of the many charming farmhouses or Tuscany villas because they are all so beautiful and get booked very quicky.

There are many wonderful and unique farmhouses and Tuscany villas to suit any vacation dream so do take the time to choose which ones meet your vacation checklist.

The difficult task will be making your final selection.

Italian Vacation Farm Near Montalcino Tuscany
Enjoy the Tuscany Countryside with its Cypress-Lined Roadways

All of Tuscany is stunning, but here I am featuring Val d’Orcia, a region of southern Tuscany which extends from the hills south of Siena to Monte Amiata and characterised by gentle, meticulously-cultivated hills and picturesque towns and villages such as Pienza and Radicofani.


On your Italian vacation, include a visit to car-free Montepulciano and its vineyards for one of Italy’s oldest wine, Vino Nobile di Montepulciano.

While you are in Montepulciano you may want to visit Cortona, the main filming location of the famous movie “Under the Tuscan Sun”.

Italian Vacation Farmhouse near Valdorcia
There are Fantastic Farmhouses and Tuscany Villas that You can Rent for Your Italian Vacation

Tuscany has a landscape which has become familiar through its depiction in works of art from the Renaissance painting to the modern photograph.

Italian Vacation a Villa in Southern Tuscany
A Villa Near Montalcino Valdoricia

Val d’Orcia is blessed with luxurious spa baths and springs to enjoy on your Italian vacation, such as Bagno Vignoni, Terme di San Filippo, Chianciano Terme and San Casciano dei Bagni.

Herons and kestrels can be seen on the paved hiking path that leads from Rocca d’Orcia to the castle of Ripa d’Orcia and on to Bagno Vignoni.

Italian Vacation in a Hamlet in Val d’Orcia

On one of my visits to Italy, I and a group of friends decided to stay at one of the beautiful Tuscany villa San Simeone in a hamlet in Val d’Orcia.

Italian Vacation at San Simeone Tuscany
Hotel San Simeone in Southern Tuscany

Hotel San Simeone is located in the medieval village of Rocca d’Orcia in a magnificent corner of the Province of Siena.

Italian Vacation at Hotel San Simeone
Front Entrance to Hotel San Simione

This Tuscany villa hotel offers refined and luxurious bed and breakfast accommodations for your Italian vacation in southern Tuscany.

Italian Vacation Luxury Villa San Simeone Valdorcia
Breakfast was Fantastic at Hotel San Simeone in Valdorcia

It’s a little challenging to find the hotel and to drive up the steep cobblestone driveway, so try to arrive during the day.

We arrived at night in a heavy thunderstorm and the experience was like a drama movie with lightening flashes surrounding the hamlet and the castle.

We continue to laugh about the adventures of our Italy vacations.

Italian Vacation Views of Valdorcia Tuscany
Views of Valdorcia Valley

The next day we awoke to a beautiful Tuscan morning with breathtaking views of the fog in the valley which lifted as the sun got hotter.

We had breakfast on the terrace high above Val d’Orcia and the hot water springs of Bagno Vignoni.

Italian Vacation Breakfast on the San Simeone Terrace in Valdorcia Tuscany
Breakfast on the Terrace at Hotel San Simeone

After the fog lifted, we could see Radicofani in the south, the castle at Ripa d’Orcia or San Quirico d’Orcia in the north and west, and Pienza and Montepulciano in the east.

The October sun was warm on this splendid morning as we relaxed and enjoyed the view of Tuscany and savoured our espresso, cappuccino and haute cuisine.

Italian Vacation View of Valdorcia from Hotel San Simeone
View of Tuscany from Valdorcia

It felt surreal and heavenly.

I had to pinch myself to realize that I was really here overlooking this glorious view of Tuscany.

Italian Vacations Views ot San Quirico d'Orcia
Views of the Countryside of San Quirico d’Orcia

I gladly recommend a southern Tuscany Italian vacation at Hotel San Simeone.

The accommodations in this ancient villa are exquisite.

Italian Vacation Suites at San Simeone Valdorcia Tuscany
A Suite at Hotel San Simeone Valdorcia

If you want to escape to a quiet yet adventurous dream world, this is the place for you.

Here you can enjoy antiquity, peaceful countryside settings, stunning vistas of Tuscany, and luxury.

Italian Vacations Luxury Accommodations at Hotel San Simeone Valdorcia
Villa at Rocca d’Orcia

Here you are surrounded by world famous vineyards and magical hiking trails.

If you are staying at the Hotel San Simeone, you will be treated by the jewel of a swimming pool overlooking the Val d’Orcia valley of Tuscany and the enchantining rock gardens embracing the villa.

Italian Vacation Luxury Swimming Pool at Hotel San Simeone Valdorcia
Spectacular Pool at Hotel San Simeone in Valdorcia

Not far are the vineyards of Montalcino and the medieval towns of Castiglion d’Orcia, Pienza, Radicofani and Montepulciano, and for your Italian vacation, the holiday experience is all about relaxation and beauty.

Italian Vacation Hotel San Simeone Valdorcia Tuscany
Morning Sun at Hotel San Simeone in Valdorcia

A short walk from Hotel San Simeone is the Rocca di Tentennano, the fortress standing high on the summit of a craggy rock above the small medieval village of the Rocca d’Orcia, and overlooking the valley of Val d’Orcia.

The Rocca di Tentennano is constructed of limestone and, like so many other castles in the area, played a role in the never-ending territorial conflicts between Florence and Siena.

Some History for Your Italian Vacation

Most of the Rocca was built around 1250 – 1258, but the peak on which it stands was used as a military lookout and point of defence from the 10th century onward.

To visit the medieval village of Rocca d’Orcia and the fortress Rocca di Tentennano, it is best to park at the foot of the steep slope leading up to the fortress.

Italy Vacation Rocca d'Orcia in Valdorcia Tuscany
The Steep Streets of Rocca d’Orcia

You can then walk along the cypress-lined hill that leads to the main entrance. Looking down, you can see the rocky and steep little village of Rocca d’Orcia which lies directly below the terraces of the Rocca.

After your visit to the fortress, take a stroll down into Rocca d’Orcia and visit the Chiesa di San Simeone, a church which was built in 1200 AD. This ancient church once housed art treasures that were stolen in the 1980s.

Italian Vacation Piazza del Cisterna Near Chiesa di San Simeone Valdorcia
The Well at Piazza del Cisternia at Rocca D’Orcia

A cobblestone walkway leads from Chiesa di San Simeone through the main part of the village, the Borgo Maestro, and nearby lies the Piazza del Cisterna, a tiny but rich Folk Art Museum, and the ruins of the Palazzo Comunale.

For your Italian vacation in this hamlet, the village has a grocery store, a couple of romantic restaurants and a charming bar on route to the Rocca di Tentennano where you can meet and chat with the friendly locals.

Italian Vacations in Valdorcia Tuscany
A Romantic Restaurant in the Village of Rocca d’Orcia

From Rocca di Tentennano you can see the twin town and nearby ruined fortress of Castiglione d’Orcia.

The views of the fortress are absolutely stunning.

Italian Vacation Castiglione Val d'Orcia Near Rocca d'Orcia
View of Castiglione d’Orcia

The hamlet Castiglione d’Orcia and imposing fortress can be seen from a great distance away.

The morning sunrise in Tuscany is fabulous.

Italian Vacation Sunrise in Valdorcia Tuscany at Tuscany Hotels San Simeone
A Morning Walk in Valdorcia Southern Tuscany

You have to plan a morning stroll and experience Tuscany when the cock crows, and the fog is lifting above the vineyards and the olive groves and magically reveals the cypress trees which guard Tuscany.

Italian Vacation Farmhouse in Tuscany
Discover Romantic Tuscan Farmhouses and Villas on Your Italian Vacation ]]>


In Tuscany, whether you are planning a family vacation or a romantic holiday, you can escape to the medieval ages in modern times.

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