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Tuscany: Val d’Orcia Travel Guide and Best Stay


Bucolic lifestyle, quaint hill towns, postcard worthy landscapes, rolling hills and cypress trees adorning the landscape, THIS is quintessential Tuscany.

This is going to be a 3 part series about the charming Tuscan countryside. There is so much to write about Tuscany. I felt that one big post is too long and does not do justice to this beautiful region of Italy. Tuscany is one of the most beautiful places and every place is gorgeous. You would need at least 3-4 days and some people ideally spend a week there.  We have explored parts of southern Tuscany: The city of Siena, the Chianti region, hill towns of Montepulciano, Montalcino, San Gimignano, Val d’Orcia and Crete Senesi. This is a 4-day itinerary if you are planning to visit.


Renting a car is ideal to explore the countryside of Tuscany. Having a car gives you the flexibility to stop wherever you want and take a picture of the poppy fields or capture that picture perfect postcard of Tuscany. It also gives you more time to actually explore places than spend time in transit. Taking a tour with a company may be another option but you would be limited by the tour’s schedule. For convenience, we rented a car from Chiusi and dropped it off in Florence. 


When in Tuscany, you must stay in an Agriturismo. Agriturismos are farm houses that open their homes to tourists and offer bed and breakfast. In some cases, they also offer cooking classes, wine tours etc. This is an authentic Tuscan experience. This was also our best stay in Italy. Where else would one get to stay in an 18th century Villa on a hill top, wake up to the rooster crowing and birds singing delicately, peer through the window and watch the sun rising over the mountains, open the door to unobstructed views of rolling hills and olives groves and vineyards, feel the wet grass as you walk around, watch the carefully tended garden flowers come to life on a beautiful spring day and at the end of the day, while watching the sunset by the pool sipping some Brunello and feeling grateful for the hospitality of your amazing hosts, you pause for a moment and realize this isn’t a dream… This is the charm of Tuscany. Oh, how I wish we had more time.

Some tips: Choose an Agriturismo centrally located to the places you’d like to explore. We stayed in a place called Agriturismo Podere Cunina in Buonconvento and it was surreal. The hosts Silvana and her husband were sweethearts and made us feel right at home. I would definitely recommend this place to anyone who is planning to visit Val d’Orcia or Siena. Look at the pictures and decide for yourself!

Val d’Orcia

Val d’Orcia is the heart of Tuscany, the picture perfect Tuscany you see on every postcard. It’s gorgeous landscape has been depicted in works of iconic renaissance painters. In Val d’Orcia, such care is given to aesthetics for centuries that you cannot help but marvel at it’s beauty. Rolling hills culminate with a villa atop, cypress groves pave the path while bed of wild poppies urge you to stop and notice them. This landscape has been so well preserved for centuries and protected by UNESCO.

According to UNESCO,

The landscape of Val d’Orcia is part of the agricultural hinterland of Siena, redrawn and developed when it was integrated in the territory of the city-state in the 14th and 15th centuries to reflect an idealized model of good governance and to create an aesthetically pleasing picture. The landscape’s distinctive aesthetics, flat chalk plains out of which rise almost conical hills with fortified settlements on top, inspired many artists. Their images have come to exemplify the beauty of well-managed Renaissance agricultural landscapes.

Even though Val d’Orcia has small area to cover, you will make a lot of stops and time soon flies by. The hill towns are unique and charming and the views of the valley from these towns are not to be missed.

The Drive

We drove from Chiusi to Val d’Orcia. On the way, we stopped at Montepulciano. I am going to write about Montepulciano in a latter wine-themed post but if you are going to follow this itinerary, definitely stop at Montepulciano.

Montepulciano to Pienza is only 14km away through the main highway but I strongly recommend taking the scenic route of SP88, SP53 through Val d’Orcia, Bagno Vignoni and San Quirico d’Orcia. This is one of the most scenic and picturesque drives. All through the drive, you will find some gorgeous views of the valley. Take in the views and stop every now and then at a winery or a poppy field and appreciate the valley’s beauty. 

The drive takes a lot more time than you’d anticipate and by the time you reach San Quirico, you will be starving!

San Quirico is a cute hilltown with amazing views of Val d’Orcia. It is a small town and easy to walk around with the most beautiful gardens!

From San Quirico, I suggest driving a little north before heading to Pienza. A few kms north of San Quirico is where you will find the famous circle of Cypresses. Deeply breathe in the fresh air and absorb the 360degree views of the majestic landscape!

San Quirico to Pienza is another 10km with a few more picturesque spots. Once you arrive in Pienza, the first thing to do is try the Pecorino cheese. It is a famous cheese made with sheep’s milk in Pienza. Not everyone might like it but it is one of the best cheeses made of sheep’s milk. Pienza is a quaint town with a unique character. You’d think all these towns would look the same but each one has a character of it’s own. You will find something interesting in each town. Have dinner or just chill with a glass of wine. The valley’s best views can also be found along the walls of Pienza. Pienza is a nice town to stay if you prefer hill towns to agritourismos. There are several Agritourismos in the area to choose from as well.

I’m sure you’ll are tired of reading me raving about the valley. Take a good rest and chill at your choice of stay. The next day, we’ll head out to the wine countries of Tuscany! Exciting!

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Hi there!

I am Aswani Kurra. I am a luxury travel expert and a Certified Sommelier who traveled extensively in Italy and the Mediterranean and lived in multiple countries including the state of California for 15 years. Join me as I share luxurious itineraries and bucketlist destinations from vineyards of California to the rolling hills of Tuscany, sweeping views of the Amalfi Coast and more.

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  1. Sami on June 23, 2020 at 9:43 pm

    Your photos of Tuscany are so lovely and make me so sad my trip got delayed earlier this year!

    • Aswani on June 25, 2020 at 12:21 am

      Aww. Hope you can reschedule it soon. I know we’ve all had to cancel a lot of travel plans. Thank you so much Sami!

  2. Ellen on February 28, 2022 at 4:14 am

    Hey! When did you go to Tuscany? I’m thinking of going in April as I want the fields to be green! Do you think that’s the case? Thank you in advance! 🙂

    • Aswani on March 3, 2022 at 4:47 am

      Hey! We went end of May and it was gorgeous. I think April would be beautiful too as it is spring time. Enjoy! 🙂

  3. Andia on April 12, 2022 at 3:48 am

    Can you please post where your photos were taken? They are stunning

  4. Paige on December 13, 2022 at 5:42 am

    Can you link the home that you stayed in? We are traveling there in September:)!

  5. Mariana on February 19, 2023 at 4:23 am

    Thank you for shearing all this information. It is very helpful and interesting to be red.

  6. Nimisha on March 1, 2023 at 1:43 am

    Lovely post!
    You mentioned offbeat cities, no mention of cities like Florence, Siena. Is it not worth going there..pls share your thoughts

    • Aswani on April 9, 2023 at 11:33 am

      We had visited both Florence and Siena and love the cities. This post is focused on the off beat areas as not many people venture out of the cities in Tuscany.

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