Exploring Val d'Orcia with IntoTuscany

Why visit Val d’Orcia in Tuscany?

Immerse yourself fully in Val d’Orcia, making cheese in the countryside and living the region from the inside, without having to manage a single logistical detail, even if you’re used to planning every trip yourself.

Val d’Orcia, a UNESCO World Heritage site, offers an enchanting blend of natural beauty, rich history, and authentic Italian culture.

You might have spotted glimpses of this beautiful region in famous movies like The Gladiator, The English Patient, and Under the Tuscan Sun. If you dream of spending a few days in a quiet and serene countryside, Val d’Orcia is definitely for you.

Just an hour south of Siena, and far enough from the over-touristy and overcrowded Florence, this valley offers rolling hills, cypress-lined roads, and picturesque vineyards. It’s a perfect destination for travelers seeking tranquility, a soothing landscape, and delicious, genuine food.

2026 Tours at a glance

OCTOBER 26th-30th 2026

or Anytime in the Spring and Fall (5 days and 4 nights)

Price per person:

  • Single occupancy, starting at US $ 3800
  • Double occupancy, starting at US $ 3500
Inquire here

Day-to-day itinerary Exploring Val d'Orcia Tour

  • Day 1: Arrival and Introductions

2:00 PM: Transfer from Florence with a private driver to our agriturismo in Val d’Orcia.
• Afternoon: Check-in and settle into our rooms.
• Evening: Meet our local guide in Pienza for a delightful stroll to discover the village, followed by aperitivo and dinner.

  • Day 2: Let’s cook together traditional Tuscan food!

Breakfast at the agriturismo
Morning: Head to the hills of Montepulciano for a cooking class with
Pamela Sheldon Johns, author of the cookbook Cucina Povera. Pamela’s property has a 15-acre olive grove where she produces her own olive oil. As a certified olive oil sommelier, she will guide us through an olive oil tasting and a tour of her grove.
We will cook several dishes together and enjoy lunch.
Afternoon: Visit Montepulciano with a local guide for a town tour, aperitivo, and dinner.

  • Day 3: Cheese Making Day

Morning: Drive to Pienza to meet Ulisse, owner and cheese maker of Podere il Casale. You’ll get to see all it takes to produce delicious raw pecorino cheese and enjoy a real farm to table lunch in one of the most beautiful location of Val D’Orcia.

Afternoon: Free time

Evening: cozy dinner at Agriturismo

  • Day 4: Flower Farm Experience

Morning: Breakfast at agriturismo.

 

Late Morning: Drive to a beautiful flower farm run by three sisters. Each season bring something beautiful in the garden, making it a little corner of paradise! We will tour the farm, pick flowers, learn preservation techniques, and create a composition to take home. Enjoy lunch at the farm with local Tuscan products under a centuries-old olive tree.

Late Afternoon: Head to Bagno Vignoni, a tiny village with thermal baths. We will relax in the hot springs and conclude the day with aperitivo and dinner at a local osteria.

  • Day 5: Wine Tasting

Morning: Breakfast at agriturismo
Late Morning:Drive to Montalcino, home of Brunello wine. Visit the town and then head to a small family farm to for a wine tasting and lunch
Late Afternoon: Drive back to Florence.

Choose Exploring Val d' Orcia tour if:

    • You’re passionate about food and how it’s produced and prepared
    • You love history and art and local stories.
    • You get inspired by artisans who are passionate about their craft
    • You love to spend time getting to know one region, instead of endlessly moving from place to place
    • You love to be in the countryside 
    • You appreciate comfort and relax, but want to do as well as to see.  

Accommodations

5 nights in Agriturismo near San Quirico d'Orcia

Price per person:
-Single occupancy, starting at US$ 3745
- Double occupancy, starting at US $3470

What’s included

Private transfer from Florence to Val d'Orcia and back

Private driver

A host and local guides

5 nights in a beautiful agriturismo

All meals: 5 breakfast, 4 lunches, 5 dinners (including wine) All planned outings and experiences

What’s not included

Airfare
Travel insurance (highly recommended)

You’ll come away from the Exploring Val d'Orcia tour:

    • Inspired by local farmers and makers
    • Relaxed, recharged, and eager to return to your daily life with new energy
    • Excited to share what you’ve learned in cooking and food preparation with your family and friends
    • Appreciative of local wines, cheeses, and olive oil not only for their taste, but also for the stories about how and where they were produced
    • Certain your slow tourism experience helped local farmers and artisans to live and prosper in the place they love
Jodi G, New York State
Carol G., New York State
Ratna O. Toronto, CA

Giuditta is a perfect guide, an organizer par excellence. Her local knowledge of the region, its hidden and other secrets as well as her connections with the community all served to make our trip to Greve unforgettable.

Anders G. Los Altos, California

When she had answered all our questions and was wondering if we were ready for cheese, my children were standing close by her and a few years older. For my part, besides being star struck, I was deeply appreciative as a parent, whispering to my wife that the last hour had been worth the family’s airfare to Italy

Golijeh Los Altos, California

The goats, the goat farm, the natural surroundings, all the ancient buildings and traditions that are still in use, all together really went right into my heart and made me feel connected, as if I had belonged to that land in some past life

Private Tour

Can’t travel on the dates above? No problem!
The Exploring Val d’Orcia tour is available year-round, with each season offering unique experiences.

Please contact me for more information. We love to accommodate families and small groups and will customize the tour to suit your schedule and preferences.

Yes, I want to know more

FAQ

We accept payment by credit card or check.

You can find our cancellation policy in our Terms and Conditions document by clicking here.

Absolutely! Giuditta will help you with suggestions and help with reservations.

We mainly walk on medieval villages, through small streets without cars. Walks are generally no longer that 1 km/0.6 mile. Given the ancient nature of the streets, the terrain can be uneven. We recommend comfortable shoes.

Unfortunately the agriturismo doesn’t provide a laundry service..

Nope! You don’t need to tip in restaurants or bars. Not should you tip guides or drivers. Tipping is a North American tradition that hasn’t taken root in Italy. For more about why you don’t need to tip in Italy, listen to my podcast here.

Absolutely! As professionals, they set their own pricing. We love to work with small farmers and makers and build strong relationships for the long term. That means that we sometimes suggest that they raise their prices if we think they’re undercharging.

Yes, we highly recommend travel insurance. 

Absolutely! Giuditta will work with you to accommodate your food preferences as much as possible. 

Let me take care of curating the best possible experience for you. And I’m always happy to customize the experience to your personal requirements.

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My Tuscan Roots is a newsletter from Into Tuscany, where I share stories, insights, and behind-the-scenes moments from curating boutique journeys across Tuscany and beyond, seeing familiar places with new purpose and guiding others to experience them deeply.